# Jolly Trolley > Rehoboth Beach's Original Mass Transit System ## Pages - [Delaware Brewery & Wine Tours](https://www.jollytrolley.com/delaware-brewery-wine-tours/): Delaware Brewery & Wine Tours Jolly Trolley Tours Southern Delaware quietly built one of the best beer-and-wine scenes on the... - [BWI Airport Car Service to the Delaware Beaches](https://www.jollytrolley.com/bwi-airport-car-service/): BWI Airport Car Service to the Delaware Beaches Jolly Trolley Airport Transportation BWI is where the cheap fares live, and... - [PHL Airport Car Service to the Delaware Beaches](https://www.jollytrolley.com/phl-airport-car-service/): PHL Airport Car Service to the Delaware Beaches Jolly Trolley Airport Transportation Philadelphia International Airport is the region’s biggest hub,... - [Car Service in Milton, Delaware](https://www.jollytrolley.com/milton-car-service/): Car Service in Milton, Delaware Jolly Trolley Car Service Milton is one of southern Delaware’s treasures: a historic shipbuilding town... - [Car Service in Millsboro, Delaware](https://www.jollytrolley.com/millsboro-car-service/): Car Service in Millsboro, Delaware Jolly Trolley Car Service Millsboro sits at the crossroads of Sussex County, one of the... - [Car Service in Bethany Beach, Delaware](https://www.jollytrolley.com/bethany-beach-car-service/): Car Service in Bethany Beach, Delaware Jolly Trolley Car Service Bethany Beach anchors Delaware’s Quiet Resorts, and quiet is exactly... - [Car Service in Lewes, Delaware](https://www.jollytrolley.com/lewes-car-service/): Car Service in Lewes, Delaware Jolly Trolley Car Service Lewes calls itself the first town in the first state, and... - [Blog](https://www.jollytrolley.com/blog/) - [Jolly Bus (seats 28)](https://www.jollytrolley.com/our-fleet/jolly-bus-seats-28/): The Jolly Trolley Jolly Bus Make a Reservation Seats 28 Our 28 passenger Jolly Bus features premium leather seats, overhead... - [Leave Us a Review](https://www.jollytrolley.com/review-us/): Share Your Experience With Us! Review Our Charter Services Thank you for traveling with the Jolly Trolley Charter services! Your... - [Rehoboth Art League Events Page](https://www.jollytrolley.com/ral-event-shuttle/): – Rehoboth Art League Events – Rehoboth Art League Event Transportation! Jolly Trolley Charter Services provides safe and reliable transportation... - [Premium Classic Trolley (seats 36 max)](https://www.jollytrolley.com/our-fleet/premium-classic-trolley/): The Jolly Trolley Premium Classic Trolley Make a Reservation Seats up to 36 Our Premium Classic Trolley seats 36 passengers,... - [Team Building Activities](https://www.jollytrolley.com/team-building/): Corporate Services Team Building Activities Make a Reservation Safe and Reliable Transportation for your next Team Building Event! Volunteer Projects... - [Special Events & Occasions](https://www.jollytrolley.com/year-round-services/special-events/): Year Round Services Special Events & Occasions Make a Reservation For life’s biggest moments our professional transportation team has the... - [Opportunities](https://www.jollytrolley.com/about/opportunities/): The Jolly Trolley Opportunities Advertise with Us! Reach the Heart of Rehoboth Beach, Dewey Beach and Southern Delaware with moving... - [FAQs](https://www.jollytrolley.com/about/faqs/): Jolly Trolley Shuttle Service Frequently Asked Questions – Seasonal Shuttle – Frequently Asked Questions The World’s Original since 1970, the... - [Testimonials](https://www.jollytrolley.com/about/testimonials/): The Jolly Trolley Testimonials Let our valued clients, passengers & Jolly Riders tell the story – Hear From: – Marie... - [Our Family](https://www.jollytrolley.com/about/our-family/): The Jolly Trolley Our Family Your Iconic Transportation Service since 1970 The World’s Original Jolly Trolley originated in 1970 as... - [About Us](https://www.jollytrolley.com/about/): The Jolly Trolley About Us Your Iconic Transportation Service Since 1970! The World’s Original Jolly Trolley originated in 1970 as... - [Corporate Services](https://www.jollytrolley.com/corporate-services/): The Jolly Trolley Corporate Services Make a Reservation Safe and Reliable Transportation for your next Corporate Event For over 30... - [Jolly Lincoln Nautiluses](https://www.jollytrolley.com/our-fleet/jolly-lincoln-nautiluses/): The Jolly Trolley Lincoln Nautilus Make a Reservation Seats 3 w/ Luggage Our fleet of Lincoln Nautilus Mid-Size SUVs seat... - [Jolly FT](https://www.jollytrolley.com/our-fleet/jolly-ft/): The Jolly Trolley Jolly FT Van Make a Reservation Seats up to 14 Our Jolly FT seats up to 14... - [Jolly Bus (seats 25)](https://www.jollytrolley.com/our-fleet/jolly-bus-seats-25/): The Jolly Trolley Jolly Bus Make a Reservation Seats 25 The Jolly Bus – Touring Model is our NEW Jolly... - [Jolly Bus (seats 32)](https://www.jollytrolley.com/our-fleet/jolly-bus-seats-32/): The Jolly Trolley Jolly Bus Make a Reservation Seats 32 The Jolly Bus seats 32 passengers with light luggage, and... - [Jolly Bus (seats 38, or 30 w/large luggage space)](https://www.jollytrolley.com/our-fleet/jolly-bus-seats-38-or-30-w-large-luggage-space/): The Jolly Trolley Jolly Bus Make a Reservation Seats 38, or 30 w/ Large Luggage Space Our 38 passenger Jolly... - [Classic Trolleys](https://www.jollytrolley.com/our-fleet/classic-trolleys/): The Jolly Trolley Classic Trolleys Make a Reservation Seats 28 to 36 Our Classic Trolleys seat 28 to 36 passengers,... - [Our Fleet](https://www.jollytrolley.com/our-fleet/): The Jolly Trolley Our Fleet Make a Reservation Reserve our Vehicles Today! From Wedding Party & Guest transportation to Large... - [Year-Round Services](https://www.jollytrolley.com/year-round-services/): Year-Round Services Make a Reservation Our Private Transportation Services Trusted since 1992 we have provided safe and reliable transportation services... - [Seasonal Rehoboth-Dewey Shuttle](https://www.jollytrolley.com/shuttle-information/): Jolly Trolley Seasonal Rehoboth-Dewey Shuttle Fixed Route Shuttle FAQ Shuttle Map & Schedule Track the Trolley Day & One-Way Tickets... - [Local Events](https://www.jollytrolley.com/year-round-services/local-events/): Year Round Services Local & Non-Profit Events Make a Reservation Local & Non-Profit Events When planning a large event we... - [Proms/Homecoming](https://www.jollytrolley.com/year-round-services/proms-homecoming/): The Jolly Trolley Proms/Homecoming Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation... - [Concerts & Sports Venues](https://www.jollytrolley.com/year-round-services/concerts-sports-venues/): Year Round Services Concerts & Sports Venues Make a Reservation Freeman Arts Pavilion Ocean City Festivals Philadelphia Washington D. C.... - [Celebrations of Life](https://www.jollytrolley.com/year-round-services/celebrations-of-life/): The Jolly Trolley Celebrations of Life Make a Reservation Your Special Event Specialists Since 1992 we have provided safe and... - [Bar/Bat Mitzvah](https://www.jollytrolley.com/year-round-services/bar-bat-mitzvah/): The Jolly Trolley Bar/Bat Mitzvah Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered... - [Bachelor/Bachelorette](https://www.jollytrolley.com/year-round-services/bachelor-bachelorette/): The Jolly Trolley Bachelor/Bachelorette Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation... - [Birthday](https://www.jollytrolley.com/year-round-services/birthday/): The Jolly Trolley Birthday Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation... - [Night Out](https://www.jollytrolley.com/year-round-services/night-out/): The Jolly Trolley Night Out Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered... - [Tours](https://www.jollytrolley.com/year-round-services/tours/): Year Round Services Jolly Trolley Tours Make a Reservation Customized & Scheduled Tours Experience stress free travel to inspiring destinations... - [Airport Transit](https://www.jollytrolley.com/year-round-services/airport-black-car-services/): Year Round Services Private Airport Transfers & Black Car Service Make a Reservation When traveling for work, planning a family... - [Weddings](https://www.jollytrolley.com/year-round-services/weddings/): Year Round Services Weddings Make a Reservation Wedding Day Specialists Your wedding day should arrive on time, every time. Since... - [Contact](https://www.jollytrolley.com/contact/): The Jolly Trolley Contact Us Make a Reservation We would love to hear from you! Please fill out the form... - [Home](https://www.jollytrolley.com/): Award Winning Professional Transportation Services – Exceeding Expectations Year Round – Rehoboth-Dewey Seasonal Shuttle Information Year-Round Reservations Weddings Airport Transit... ## Posts - [How to Plan Corporate Event Transportation in Southern Delaware: A Checklist](https://www.jollytrolley.com/how-to-plan-corporate-event-transportation-in-southern-delaware-a-checklist/): A corporate event is judged on a hundred details, but transportation is the one everyone notices when it goes wrong.... - [What to Look for in a Delaware Beach Transportation Company](https://www.jollytrolley.com/choosing-a-delaware-beach-transportation-company/): Booking transportation for a wedding, an airport run or a corporate event should be simple, but from the outside most... - [Wedding Day Transportation Planning: A Guide for Delaware Beach Weddings](https://www.jollytrolley.com/delaware-wedding-transportation-guide/): Your wedding day is one of the most important days of your life. Family and friends are traveling from near... - [Our Jolly History: From 1970 to Today](https://www.jollytrolley.com/history-of-the-jolly-trolley/): The Jolly Trolley and its bright, colorful vehicles are a local icon, a familiar sight between Rehoboth Beach and Dewey... - [Day Trips from Southern Delaware: DC, Philadelphia, NYC and Closer to Home](https://www.jollytrolley.com/day-trips-from-southern-delaware/): One of the best things about living in or visiting the Delaware beaches is how much sits within a day’s... - [PHL, BWI or Salisbury? Choosing the Best Airport for Your Delaware Beach Trip](https://www.jollytrolley.com/choosing-the-best-airport-for-your-delaware-beach-trip/): Planning a trip to the Delaware beaches, or bringing family and guests in from out of town? The first decision... # # Detailed Content ## Pages - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/delaware-brewery-wine-tours/ Delaware Brewery & Wine Tours Jolly Trolley Tours Southern Delaware quietly built one of the best beer-and-wine scenes on the East Coast, from a world-famous brewery in Milton to Delaware's first winery in Lewes and a string of taprooms in between. Jolly Trolley runs private brewery and wine tours across all of it: your group, your stops, your schedule, and a professional driver so nobody counts their tastings. How Our Brewery Tours Work Every tour is private and built around your group. Pick three to five stops (we will happily suggest a route), and we handle the rest: pickup at your rental home, hotel or venue anywhere in the beach towns, comfortable rides between stops, and a safe trip home at the end. Most tours run four to six hours. Groups from 2 to 36 ride in the vehicle that fits, and yes, you can do the whole thing in one of our iconic classic trolleys, which tends to upgrade the day from outing to event. The Classic Stops Dogfish Head (Milton): the bucket-list brewery, with tastings at the Milton brewery itself. Nassau Valley Vineyards (Lewes): Delaware's first winery. The Lewes taprooms: Big Oyster and Crooked Hammock anchor an easy multi-stop loop. Rehoboth's craft row: Revelation and Thompson Island, minutes from the boardwalk. Dewey Beer Co. (Dewey Beach): the beach-town favorite. Salted Vines Vineyard (near Bethany Beach): the southern winery stop for Quiet Resorts groups. The local lineup keeps growing, and hours change seasonally, so tell us your date and... - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/bwi-airport-car-service/ BWI Airport Car Service to the Delaware Beaches Jolly Trolley Airport Transportation BWI is where the cheap fares live, and for many Delaware beach travelers the savings on a Southwest or budget-carrier ticket more than cover a comfortable ride to the coast. Jolly Trolley provides private car service between BWI Marshall Airport and the Delaware beaches: black cars, vans and mini buses, flight tracking on every pickup, and drivers who have crossed the Bay Bridge more times than they can count. Door-to-Door from BWI, However You Land Send us your flight number and your ride is handled. We watch your arrival in real time, adjust for delays automatically, and meet you curbside at arrivals, with baggage-claim meet-and-greet available on request. From there it is one vehicle, one driver, straight to your door at the beach. No connections, no surge pricing, no two-hour rideshare gamble. BWI to Every Delaware Beach Town Typical drive times from BWI: Rehoboth Beach: about 2 hours 15 minutes to downtown and the boardwalk. Dewey Beach: roughly 2 hours 15 minutes. Lewes: about 2 hours 15 minutes, including ferry terminal connections. Millsboro: around 2 hours 15 minutes via Route 404 and 113. Milton: about 2 hours 15 minutes. Bethany Beach: roughly 2 and a half hours, covering all of the Quiet Resorts. The Bay Bridge, Handled Every BWI-to-beach trip crosses the Chesapeake Bay Bridge, and on summer weekends that crossing is the difference between a smooth ride and a two-hour crawl. Our drivers run this corridor every... - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/phl-airport-car-service/ PHL Airport Car Service to the Delaware Beaches Jolly Trolley Airport Transportation Philadelphia International Airport is the region's biggest hub, and for most Delaware beach travelers it is the first or last leg of the trip. Jolly Trolley runs private car service between PHL and the Delaware beaches every week: black cars for individuals and couples, vans and mini buses for families and groups, with flight tracking on every single pickup. We have been driving this route since before GPS existed. Door-to-Door Service from PHL Give us your flight number and forget the rest. We monitor your arrival in real time, so an early landing or a two-hour delay adjusts your pickup automatically. Your driver meets you curbside at arrivals (meet-and-greet inside baggage claim is available on request), loads your luggage, and takes you straight to your door, rental home, or hotel. No shuttle transfers in Wilmington, no hoping a rideshare driver accepts a two-hour trip. PHL to Every Delaware Beach Town We serve every town at the beach and inland Sussex County. Typical drive times from PHL: Milton: about 2 hours, the shortest beach-area run from Philadelphia. Lewes: about 2 hours, including Cape May-Lewes Ferry connections. Rehoboth Beach: roughly 2 hours 15 minutes to downtown or the boardwalk hotels. Dewey Beach: about 2 hours 15 minutes. Millsboro: around 2 hours 15 minutes for Long Neck and the Indian River communities. Bethany Beach: about 2 and a half hours, serving all of the Quiet Resorts. Summer Friday and Sunday traffic... - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/milton-car-service/ Car Service in Milton, Delaware Jolly Trolley Car Service Milton is one of southern Delaware's treasures: a historic shipbuilding town on the Broadkill River that now draws visitors from around the country to its most famous resident, Dogfish Head. Jolly Trolley provides private car service in Milton year round: black car airport transfers, brewery group rides, theatre nights and wedding transportation, from the family-run team serving southern Delaware since 1970. Private Car and Black Car Service in Milton From the Victorian homes of Milton's historic district to Broadkill Beach on the bay, our chauffeured black cars cover Milton and its surroundings in every season. Catch a show at the Milton Theatre without thinking about parking, head to dinner in Lewes or Rehoboth Beach, or set up a comfortable ride for visiting guests. Scheduled service, professional drivers, no seasonal disappearing act. Airport Transfers from Milton As the northernmost of the beach-area towns, Milton enjoys the shortest runs to Philadelphia and Wilmington: Philadelphia (PHL): about two hours, the region's largest hub. Wilmington Amtrak: roughly an hour and a half for train connections to Philly, NYC and DC. Baltimore (BWI): around two and a quarter hours via the Bay Bridge. Salisbury (SBY): about 55 minutes for the closest commercial flights. Delaware Coastal (GED): minutes away in Georgetown for private and charter aviation. Every airport trip includes flight tracking, so delays adjust your pickup automatically. Not sure which airport to book? Our guide to choosing the best airport for your Delaware beach trip breaks... - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/millsboro-car-service/ Car Service in Millsboro, Delaware Jolly Trolley Car Service Millsboro sits at the crossroads of Sussex County, one of the fastest growing corners of Delaware, where Route 113 meets the road to the beaches. Jolly Trolley provides private car service in Millsboro year round: black car airport transfers, cruise port connections, weddings and group transportation, from the family-run team that has served southern Delaware since 1970. Private Car and Black Car Service in Millsboro Millsboro is a year-round town, and so are we. Our chauffeured black cars serve Millsboro, Long Neck and the Indian River Bay communities every month of the year, whether that is a ride to a dinner reservation in Rehoboth Beach, an evening event, or a comfortable trip for visiting family. When the app-based options thin out after Labor Day, our schedule does not change. Airport Transfers from Millsboro Living inland puts Millsboro closer to more travel options than most people realize: Delaware Coastal Airport (GED): just minutes up the road in Georgetown for private and charter flights. Salisbury (SBY): about 40 minutes for the closest commercial service. Philadelphia (PHL): roughly two and a quarter hours, the region's biggest hub. Baltimore (BWI): about two and a quarter hours via the Bay Bridge. Wilmington Amtrak: around an hour and forty five minutes for train connections. Every trip includes flight tracking and a driver who knows which of these routes runs cleanest at your departure hour. Comparing options? Start with our guide to choosing the best airport for your... - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/bethany-beach-car-service/ Car Service in Bethany Beach, Delaware Jolly Trolley Car Service Bethany Beach anchors Delaware's Quiet Resorts, and quiet is exactly how your transportation should feel. Jolly Trolley provides private car service in Bethany Beach: chauffeured black car airport transfers, rides to dinners and concerts, wedding shuttles and group transportation, from the family-run team that has served the Delaware beaches since 1970. Private Car and Black Car Service in Bethany Beach From a pickup at a Sea Colony rental to a dinner reservation on Garfield Parkway or a night out in Fenwick Island or Ocean City, our chauffeured black cars handle point-to-point trips throughout the Quiet Resorts year round. No surge pricing, no waiting on an app to find a driver in the off season, just a scheduled car and a professional behind the wheel. Airport Transfers from Bethany Beach Bethany Beach has a secret advantage: it is the closest of the Delaware beach towns to Salisbury Regional Airport. Here is what we drive every week: Salisbury (SBY): about 45 minutes, the shortest airport run at the beach. Baltimore (BWI): roughly two and a half hours via the Bay Bridge. Philadelphia (PHL): about two and a half hours up Route 1. Wilmington Amtrak: around two hours for train connections to Philly, NYC and DC. We track every flight, so a delay adjusts your pickup automatically. Weighing which airport makes sense? Our guide to choosing the best airport for your Delaware beach trip compares them, and our airport black car service page... - Published: 2026-07-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/lewes-car-service/ Car Service in Lewes, Delaware Jolly Trolley Car Service Lewes calls itself the first town in the first state, and getting around it should feel just as effortless as the town itself. Jolly Trolley provides private car service in Lewes, Delaware: black car airport transfers, point-to-point rides, ferry terminal pickups and group transportation, backed by a local team that has served the Delaware beaches since 1970. Private Car and Black Car Service in Lewes Whether you need a professional ride to a dinner reservation on Second Street, a pickup from a rental home near Cape Henlopen, or reliable transportation for a night out, our chauffeured black cars and larger vehicles cover Lewes year round. We are FMCSA and USDOT regulated, interstate licensed and insured, so the same team can take you across town or across state lines. Airport Transfers from Lewes Lewes sits within comfortable reach of several airports, and we drive these routes every week: Philadelphia (PHL): roughly two hours, the region's largest hub. Baltimore (BWI): about two and a quarter hours via the Bay Bridge. Salisbury (SBY): under an hour, the closest commercial airport. Wilmington Amtrak: about an hour and a half for Northeast Corridor train connections. Every airport trip includes flight tracking, so a delayed arrival means an adjusted pickup, not a missed one. Not sure which airport fits your trip? Our guide to choosing the best airport for your Delaware beach trip compares them all, and our airport black car service page covers the full list... - Published: 2025-08-15 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/jolly-bus-seats-28/ The Jolly Trolley Jolly Bus Make a Reservation Seats 28 Our 28 passenger Jolly Bus features premium leather seats, overhead storage, charging ports and reading lights for each passengers comfort. For trips long and short! Click an image below to expand: Reserve Email Us Return To Our Fleet - Published: 2025-07-30 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/review-us/ Share Your Experience With Us! Review Our Charter Services Thank you for traveling with the Jolly Trolley Charter services! Your safety and comfort are always our top priority and we work very hard behind the scenes to make sure your travel plans are performed precisely as scheduled. For over 30 years Transit U Inc & The Jolly Trolley have provided safe and reliable transportation service in Southern Delaware and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. All reviews are admired, but not required - please take the time to share your experience with our Jolly Trolley Charter services! Reviews on Google, Facebook, Trip Advisor etc. are sincerely appreciated to spread the word amongst our community & Southern Delaware. We thank you for traveling with us, and look forward to serving you again in the future! Google Reviews Facebook Reviews TripAdvisor Reviews - Published: 2025-07-07 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/ral-event-shuttle/ - Rehoboth Art League Events - Rehoboth Art League Event Transportation! Jolly Trolley Charter Services provides safe and reliable transportation for the Rehoboth Art League Cottage Tour & Outdoor Show again in 2025! We look forward to transporting you to your next Rehoboth Art League experience! For over 30 years Transit U Inc & The Jolly Trolley have provided safe and reliable transportation service in Southern Delaware and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Track Our Vehicles! Unmatched Limousine & Charter Service Our year-round Limousine and Charter Service provides our clients with experienced and customized transportation programs for trips large and small! FMCSA, & USDOT regulated, interstate licensed and insured with our Jolly Trolley Limousine Service LLC. From large groups to small, trips to all airports or around town we are here to provide safe and reliable transportation for your upcoming travel plans. Experience the Jolly Trolley Charter services today! Year Round Service Original Jolly Trolley Shuttle The Jolly Trolley Fixed Route operates from Memorial Day weekend through Labor Day Monday! BASIC SCHEDULE - Departing every 30 minutes (off-peak), :00 & :30 from our Rehoboth Avenue & the Boardwalk Stop in Rehoboth Beach, and at :15 & :45 from Dickinson St. in Dewey Beach on the Rehoboth Bay. During PEAK TRAVEL times, The Jolly Trolley arrives... - Published: 2025-04-25 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/premium-classic-trolley/ The Jolly Trolley Premium Classic Trolley Make a Reservation Seats up to 36 Our Premium Classic Trolley seats 36 passengers, and feature open air rear windows, and iconic trolley standards such as natural wood interior and seating, intricate wrought-iron seat framework, and timeless etched accent designs! Reserve our unique and iconic Premium Classic Trolleys for your Wedding Day travel plans or next Special Event at the Delaware Beaches! Click an image below to expand: Reserve Email Us - Published: 2025-04-11 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/team-building/ Corporate Services Team Building Activities Make a Reservation Safe and Reliable Transportation for your next Team Building Event! Volunteer Projects Cooking Competitions Bay or Ocean Voyages Sporting Events When its time for a team building event such as learning about a new culinary trend or artistic technique, soaking up the sun at the beach or bay, or simply enjoying a day or night on the town with fellow co-workers let us be your safe and reliable transportation to make sure your group travels together to a fun new experience! Contact us today to reserve our transportation expertise for your next corporate event! Reserve our Vehicles Email Us Hear From Our clients Sherry S. HR Director I wanted to let you know that a good time was had by all once again ! ! ! Denise was a great driver and The Jolly Trolley was the way to go! ! We will continue to sing your praises and, of course, use you again for future fun activities! - Jim L. General Manager I cannot thank you enough for the great transportation experience on Saturday. Mr. Bob was AWESOME! He is kind, accommodating and provided us great recommendations. Couldn't be happier with the choice. I will absolutely spread the word on the wonderful experience!   - Published: 2025-03-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/special-events/ Year Round Services Special Events & Occasions Make a Reservation For life's biggest moments our professional transportation team has the experience and local knowledge to help make your special day even more special! Since 1992 we have performed safe and reliable transportation for countless Special Events & Occasions and have strong relationships with all major venues in Southern Delaware. Birthday Parties Family Reunions Bachelorette/Bachelor Parties Proms/Homecoming Holiday Parties Bar/Bat Mitzvahs Celebrations of Life When you reserve our vehicles you can rest assured that we are working diligently, utilizing our proven quality control methods to make sure your event travel plans are performed as scheduled so that you can fully enjoy your special day. From our luxury sedans to our iconic Classic Trolleys, we have the perfect vehicles and professional chauffeurs ready for your upcoming event! Reserve our Vehicles Today! Hear From Our Clients - Norah L. "We booked the Jolly Trolley to transport a group of teenagers into Rehoboth for the Cape Henlopen Prom. Christine Hastings was the fabulous chauffeur and chaperone for the one mile journey and we were just thrilled. Not only was she perfectly pleasant and welcoming to our crew of 20+ teenage riders, she was as enthusiastic as they were about going to prom after two years of Covid cancellations. The Jolly Trolley is always a Rehoboth tradition but it made our kids' night even more special with a drop off right in town and right on time. I am definitely booking again next year and... - Published: 2025-01-23 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/about/opportunities/ The Jolly Trolley Opportunities Advertise with Us! Reach the Heart of Rehoboth Beach, Dewey Beach and Southern Delaware with moving Billboards for a Postcard Price. Your advertising travels with us to Weddings, and Special Events year round. Contact Us to find out how we can spread the word about your business! Please, complete the form to the right to contact us about our unique advertising opportunities ~ Email us Today! 302-644-0400 Fill out my online form. Join Our Driver & Chauffeur Team! Fill out my online form. - Published: 2025-01-23 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/about/faqs/ Jolly Trolley Shuttle Service Frequently Asked Questions - Seasonal Shuttle - Frequently Asked Questions The World's Original since 1970, the iconic Jolly Trolley has provided safe and reliable transportation for visitors and locals alike at the Delaware Beaches. The Jolly Trolley Fixed Route Shuttle Service offers relaxing beach shuttle transportation between Rehoboth Beach & Dewey Beach from Memorial Day to Labor Day. Park your car, relax, and let us take care of the driving for you! We know you're on vacation, or at least taking some well deserved time off! Let us make your life easier with a few answers to frequently asked questions that may answer any questions you have about our iconic Fixed Route Shuttle service between Rehoboth & Dewey Beach. 1. ) Bandstand Performance Pickup/Drop-off Location: - During Rehoboth Beach Bandstand performances our vehicles will pickup at the Bandstand bathrooms and will not travel to our normal Boardwalk & Bandstand Jolly Trolley Stop. 2. ) Inbound VS Outbound Travel: - When our Jolly Vehicles are traveling North to Rehoboth Beach (Ocean on the right), we are traveling Inbound. - When our Jolly Vehicles are traveling South to Dewey Beach (Ocean on the left), we are traveling Outbound. 3. ) Southbound Dewey Beach Pickups: - We recommended that all Jolly Riders in Dewey Beach wishing to travel to Rehoboth Beach to board our Trolleys at our Northbound (Inbound) Jolly Trolley Stops located approximately every two blocks in Dewey Beach. Our Jolly Vehicles may not pickup passengers who want... - Published: 2025-01-23 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/about/testimonials/ The Jolly Trolley Testimonials Let our valued clients, passengers & Jolly Riders tell the story - Hear From: - Marie W. You won't find a better transportation service. A Thoughtful, professional and caring company. - Nicole B. I have been working with Jolly Trolley professionally as a wedding planner and personally for over 5 years. They constantly deliver. Their team is friendly and accommodating. Its a joy to work with them! - Sherry L. I took the Jolly trolley to Longwood Gardens. What a wonderful experience at a great price. The driver and Deborah were very helpful and accommodating. We will-certainly will use Jolly trolley again and again and again. Thank you for a great experience - Robert A. Trip to St. Michaels. Excellent driver and hostess. Fun trip! ! - Eileen Had a great experience with Jolly Trolley yesterday. Rented one of the buses for a pub crawl group trip in Rehoboth. Our driver, Will, was wonderful and he returned us safely home! Communicated well. Great experience! - Ashley L. We had a great ride on the Jolly Trolley. Thank you for being so compassionate about our circumstances. We appreciate you being flexible to accommodate our family's needs. We made great memories - Madison I hired numerous of shuttles/busses from Jolly Trolley for my wedding day. They picked up from the hotels, took back to the hotels and served as party busses to the after party. I can not say enough about the amazing customer service and professionalism. They... - Published: 2025-01-23 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/about/our-family/ The Jolly Trolley Our Family Your Iconic Transportation Service since 1970 The World's Original Jolly Trolley originated in 1970 as the first tour transportation service in Rehoboth & Dewey Beach. Family owned and operated since 1992, the Hastings family purchased, developed, and have privately operated Transit U Inc. & the Jolly Trolley, building it into the iconic, safe and reliable service it is today in the Nation's Summer Capital! As the local transportation industry pioneer, Jolly Trolley has evolved from a seasonal trolley transportation service to a year-round leader providing a large diversified vehicle fleet and a variety of services to meet your travel needs. Throughout our expansion we have maintained our original mission statement "To provide professional, safe, reliable, stress free transportation". For over 30 years Transit U Inc & The Jolly Trolley have provided safe and reliable transportation service in Southern Delaware and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs many of whom are former business professionals, firefighters, and safety personnel. Our experienced Transportation Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods! - Published: 2025-01-23 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/about/ The Jolly Trolley About Us Your Iconic Transportation Service Since 1970! The World's Original Jolly Trolley originated in 1970 as the first tour transportation service in Rehoboth & Dewey Beach. In 1992 the Hastings family purchased, developed, and have privately operated Transit U Inc. & the Jolly Trolley, building it into the iconic, safe and reliable service it is today in the Nation's Summer Capital! We operate our year round Professional Charter Service, Private & Public Tours, School Shuttle Services, and the direct coastal Fixed Route Service between Rehoboth Beach & Dewey Beach! Leave your car parked, jump on a Jolly Trolley vehicle, and enjoy your travel the Jolly way! Learn more Unmatched Limousine & Charter Service Our year-round Limousine and Charter Service provides our clients with experienced and customized transportation programs for trips large and small! FMCSA, & USDOT regulated, interstate licensed and insured with our Jolly Trolley Limousine Service LLC. From large groups to small, trips to all airports or around town we are here to provide safe and reliable transportation for your upcoming travel plans. Experience the Jolly Trolley Charter services today! Year Round Service Original Jolly Trolley Shuttle The Jolly Trolley Fixed Route operates from Memorial Day weekend through Labor Day Monday! BASIC SCHEDULE - Departing every 30 minutes (off-peak), :00 & :30 from our Rehoboth Avenue & the Boardwalk Stop in Rehoboth Beach, and at :15 & :45 from Dickinson St. in Dewey Beach on the Rehoboth Bay. During PEAK TRAVEL times, The Jolly Trolley... - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/corporate-services/ The Jolly Trolley Corporate Services Make a Reservation Safe and Reliable Transportation for your next Corporate Event For over 30 years our transit team has provided safe and reliable transportation in southern Delaware and beyond for thousands of companies. Whatever your event needs to move, from a single executive to an entire conference, one call puts our fleet, drivers and dispatch behind your schedule. Corporate Event Transportation Company celebrations, client entertainment, holiday parties and offsites: we work directly with your company liaison on logistics and bring the local knowledge that keeps a plan realistic, from venue loading zones to summer Route 1 timing. Over three decades we have built strong relationships with all the major venues in southern Delaware, and our quality control methods and proprietary systems make sure your group arrives on time, every time. Planning one now? Our corporate event transportation checklist covers the details planners forget. Conference & Meeting Shuttles For multi-day conferences we run continuous hotel-to-venue shuttle loops with published frequencies, staged arrival waves from PHL and BWI, and consolidated billing so your accounts payable team gets one invoice instead of forty receipts. Executive Black Car & Airport Transfers Our Lincoln Nautilus black cars handle executive and client pickups with flight tracking on every run; see our airport black car service for every airport, station and cruise port we cover. En route, the quiet cabin works as well as your office does. Team Outings That Actually Bond From team building activities to brewery and winery tours,... - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/jolly-lincoln-nautiluses/ The Jolly Trolley Lincoln Nautilus Make a Reservation Seats 3 w/ Luggage Our fleet of Lincoln Nautilus Mid-Size SUVs seat up to 3 with luggage! Travel in comfort & quiet luxury, with extra luggage space and Lincoln's award winning all-wheel-drive safety systems for trips to all major Airports, Train Stations, & Cruise Ports, as well as City-to-City Transfers & Non-Emergency Medical transportation. Click an image below to expand: Reserve Email Us Return To Our Fleet - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/jolly-ft/ The Jolly Trolley Jolly FT Van Make a Reservation Seats up to 14 Our Jolly FT seats up to 14 passengers, or 8 passengers with standard luggage. Featuring premium reclining leather seats, phone charging ports, plus a large separate luggage storage area this versatile vehicle is great for travel to/from Airports & Travel Hubs, Wedding Parties, Day Trip Tour Groups, and Nights Out! Click an image below to expand: Reserve Email Us Return To Our Fleet - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/jolly-bus-seats-25/ The Jolly Trolley Jolly Bus Make a Reservation Seats 25 The Jolly Bus - Touring Model is our NEW Jolly Bus which can transport up to 25 passengers! This vehicle type is available for any type of trip. We are fully licensed and insured to provide service for local outings as well as travel out of Delaware to nearby cities and destinations for sporting events, concerts, tours or a variety of other outings. This Jolly Bus type is equipped with 6 monitors (and DVD player), overhead storage and reclining seats. A Jolly way to travel to and from your out of town destination. Click an image below to expand: Reserve Email Us Return To Our Fleet - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/jolly-bus-seats-32/ The Jolly Trolley Jolly Bus Make a Reservation Seats 32 The Jolly Bus seats 32 passengers with light luggage, and features premium seats and overhead storage for comfort for trips long and short! Click an image below to expand: Reserve Email Us Return To Our Fleet - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/jolly-bus-seats-38-or-30-w-large-luggage-space/ The Jolly Trolley Jolly Bus Make a Reservation Seats 38, or 30 w/ Large Luggage Space Our 38 passenger Jolly Bus features premium seats and overhead storage for comfort during trips long and short! Includes seating for up to 38 passengers with light carry-on luggage, or 30 with standard checked luggage. Click an image below to expand: Reserve Email Us Return To Our Fleet - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/classic-trolleys/ The Jolly Trolley Classic Trolleys Make a Reservation Seats 28 to 36 Our Classic Trolleys seat 28 to 36 passengers, and feature open air rear windows, and iconic trolley standards such as natural wood interior and seating, intricate wrought-iron seat framework, and timeless etched accent designs! Reserve our unique and iconic Classic Trolleys for your Wedding Day travel plans or next Special Event at the Delaware Beaches! Click an image below to expand: 3D Walkthrough! Reserve Email Us Return To Our Fleet - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/our-fleet/ The Jolly Trolley Our Fleet Make a Reservation Reserve our Vehicles Today! From Wedding Party & Guest transportation to Large Events & Transit Logistics, Airport Transfers to In-Town trips we are your safe and reliable professionals in transit. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Contact our Charter Office at 302-644-0200, reserve online or email us to reserve our vehicles for your upcoming travel plans! Classic Trolleys(Seats 28 to 36) Learn More Premium Classic Trolley(Seats 36) Learn More Jolly Bus (38)(Seats 38, or 30 w/standard luggage) Learn More Jolly Bus (32)(Seats 32, or 20 w/standard luggage) Learn More Jolly Bus (28)(Seats 28) Learn More Jolly Bus (25)(Seats 25) Learn More Jolly FT(Seats up to 14) Learn More Lincoln NautilusLuxury Mid-Size SUVs (Seats 3 w/ luggage) Learn More - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/ Year-Round Services Make a Reservation Our Private Transportation Services Trusted since 1992 we have provided safe and reliable transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Transportation Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Click on a tile below to learn more! Weddings Airport Transit Night Out birthday Bachelor/bachelorette Bar/Bat Mitzvah Celebrations of life Concerts & Sports Venues Proms/Homecoming Tours Local Events Non-Profit Events - Published: 2025-01-22 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/shuttle-information/ Jolly Trolley Seasonal Rehoboth-Dewey Shuttle Fixed Route Shuttle FAQ Shuttle Map & Schedule Track the Trolley Day & One-Way Tickets The World's Original since 1970! The World's Original since 1970, the iconic Jolly Trolley has provided safe and reliable transportation for visitors and locals alike at the Delaware Beaches. The Jolly Trolley Fixed Route Shuttle Service offers relaxing beach shuttle transportation between Rehoboth Beach & Dewey Beach from Memorial Day to Labor Day. Park your car, relax, and let us take care of the driving for you! Upcoming Shuttle Information Our Seasonal Shuttle Service begins Friday, May 22nd, 2026! Daily Service BEGINS - Saturday, June 13th, 2026! Friday & Saturday - 3:00pm to 12:00am Sunday to Thursday - 3:00pm to 11:00pm The Jolly Trolley Experience! 3D Trolley Walkthrough! Hear From Our Jolly Riders! - Kianna K. We go to Dewey Beach every year, but this is the first time we took the trolley into Rehoboth. This is how my family will visit the boardwalk from now on. The driver was helpful , considerate, and patient with passengers. The ride was smooth and quick. Despite the rain, hands down the one thing we will be sure to do again. - Dell T. My family and I have enjoyed the Jolley Trolley since it began. As an owner of multiple rental properties I always recommend the Jolley Trolley to my tenants. I tell them not only about it being a unique fun experience but how much easier it is not to have... - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/local-events/ Year Round Services Local & Non-Profit Events Make a Reservation Local & Non-Profit Events When planning a large event we understand that the details matter! From Cottage Tours to Holiday Events, Fundraisers to Art Shows we are your experts in mass public transportation, and have both the experience and logistical organization to make sure your event guests are transported on schedule in groups large or small. Reserve our Vehicles Email us Charter Office: (302) 644-0200 Hear from our clients - Devon C. VIP Liaison I couldn't have asked for a better experience than the one provided by Jolly Trolley. From the moment they arrived, the professionalism, punctuality, and courtesy of their team made a world of difference. The transportation was seamless, with the shuttle service offering smooth, comfortable rides to and from the festival venues. Jolly Trolley ensured that authors arrived on time and stress-free, which was so important in keeping our schedule running smoothly. Their commitment to providing top-notch service was evident, and I truly appreciated the care and attention they showed to every detail. If you're looking for reliable and friendly transportation for any event, I highly recommend Jolly Trolley. They made our festival experience fabulous! Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/proms-homecoming/ The Jolly Trolley Proms/Homecoming Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Wedding & Event Transit Logistics Private Airport Transfers Customized & Scheduled Tours Freeman Arts Pavilion Shuttle - 2026 shuttle schedule posted! Reserve Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/concerts-sports-venues/ Year Round Services Concerts & Sports Venues Make a Reservation Freeman Arts Pavilion Ocean City Festivals Philadelphia Washington D. C. Travel stress free with our safe & reliable services to the big game or can't-miss performance! Extend your experience by letting us do the driving for you, no parking/hassle or worrying about missing the opening play, our experienced chauffeur team will make sure you never miss a beat! We are your 2026 FIFA World Cup transit professionals! Our team has a passion for safe and reliable transportation - let us take care of the driving for your upcoming World Cup travel needs. We provide service throughout Delaware, Maryland and the Philadelphia Region and are ready to make sure your group arrives to the game on time and ready for a great game!   2026 Freeman Arts Pavilion Summer Shuttle Schedule Below! Click Here for our Upcoming Concert Shuttle Schedule Reserve our Vehicles Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/celebrations-of-life/ The Jolly Trolley Celebrations of Life Make a Reservation Your Special Event Specialists Since 1992 we have provided safe and reliable chartered transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Reserve our vehicles Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/bar-bat-mitzvah/ The Jolly Trolley Bar/Bat Mitzvah Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Wedding & Event Transit Logistics Private Airport Transfers Customized & Scheduled Tours Freeman Arts Pavilion Shuttle - 2026 shuttle schedule posted! Reserve Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/bachelor-bachelorette/ The Jolly Trolley Bachelor/Bachelorette Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Wedding & Event Transit Logistics Private Airport Transfers Customized & Scheduled Tours Freeman Arts Pavilion Shuttle - 2026 shuttle schedule posted! Reserve Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/birthday/ The Jolly Trolley Birthday Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Wedding & Event Transit Logistics Private Airport Transfers Customized & Scheduled Tours Freeman Arts Pavilion Shuttle - 2026 shuttle schedule posted! Reserve Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/night-out/ The Jolly Trolley Night Out Make a Reservation Our Charter Services Since 1992 we have provided safe and reliable chartered transportation services to the Delaware Beaches and beyond with fully licensed & insured vehicles, and trained & professional chauffeurs. Our experienced Charter Team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Wedding & Event Transit Logistics Private Airport Transfers Customized & Scheduled Tours Freeman Arts Pavilion Shuttle - 2026 shuttle schedule posted! Reserve Email us Charter Office: (302) 644-0200 Return To Year-Round Services - Published: 2025-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/tours/ Year Round Services Jolly Trolley Tours Make a Reservation Customized & Scheduled Tours Experience stress free travel to inspiring destinations with our customized and scheduled Tours! From our Rehoboth Beach Historical Tours & trips to the Freeman Arts Pavilion, to our Longwood Gardens Tours & trips to Washington DC, we have crafted an exciting array of upcoming trips to unique and unforgettable locations in Southern Delaware & beyond. All of our scheduled tours may also be reserved as a private tour for your travel group and are perfect for birthdays, family reunions, and bachelorette or bachelor parties! Click here for a full list of our Upcoming Tours! Upcoming Tours Freeman Arts Pavilion Shuttle Reserve Our Vehicles Private Tours Our Private Tours are the perfect transportation program for neighborhood, community, or school groups interested in traveling with our stress free tour services to inspiring destinations in the Mid-Atlantic Region. Our experienced Reservations team are familiar with all major venues in this region and we work closely with each group to schedule one of our established tours or create a custom tour based on the group's travel needs. Our diverse and organized transportation programs include pricing and tour itineraries for all tour groups large or small, with an option to include a tour host, admission/entrance ticket purchases, and private online sign up and payment link for your group members. Contact Us! Public Tours Our Public Tours are perfect for individuals or groups of 2-4 that are interested in traveling with one of... - Published: 2025-01-17 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/year-round-services/airport-black-car-services/ Year Round Services Private Airport Transfers & Black Car Service Make a Reservation When traveling for work, planning a family vacation, or only a few days away, trust our safe, reliable, fully licensed and insured Black Car services. Plan your travel on your schedule and travel exactly when you want, while utilizing our vehicles as your workplace or extending your vacation time while you relax in our vehicles. Travel with Jolly Trolley Airport Transportation & Black Car services - we provide private chauffeured transportation to all Mid-Atlantic transit hubs including: Philadelphia Airport Cape Liberty Cruise Port Wilmington Amtrak Station JFK International Airport Wilmington (ILG) Airport Newark (EWR) Dulles International BWI Airport Baltimore Cruise Terminal & Much More! Private Airport Car Service Across Southern Delaware We provide door-to-door airport transfers throughout Sussex County, including Lewes, Bethany Beach, Millsboro, Milton, Rehoboth Beach and Dewey Beach. Contact us today to experience why our Private Airport services are the best value in our market! Reserve Our Vehicles Email Us Hear From Our Clients - Annette S. After trying several local services, Jolly Trolley became our 'go to' for getting our clients to the airports. They have always been extremely reliable, arriving on time or a few minutes early with very clean and well maintained vehicles managed by professionally dressed and polite drivers. I would highly recommend them for your transportation needs. - Alexandra A. I have used Jolly Trolley on several occasions over the last three years to take me from my home in... - Published: 2025-01-17 - Modified: 2026-08-12 - URL: https://www.jollytrolley.com/year-round-services/weddings/ Year Round Services Weddings Make a Reservation Wedding Day Specialists Your wedding day should arrive on time, every time. Since 1992 we have performed hundreds of thousands of wedding trips at the Delaware beaches, and we have strong working relationships with all the major venues in southern Delaware, from beach ceremonies in Rehoboth and Dewey to receptions at landmarks like the Indian River Life Saving Station. Our team knows the loading zones, the traffic patterns and the timelines, so your day runs on schedule while you enjoy it. Every Ride Your Wedding Needs From our luxury black car sedans to our iconic Classic Trolleys, our team covers the whole day: bridal party transportation with time built in for photos, continuous guest shuttles between hotels, ceremony and reception, and a private black car send-off at the end of the night. Our full fleet handles wedding parties and guest lists of every size. Serving Every Wedding Town at the Beach We provide wedding transportation throughout southern Delaware, including Rehoboth Beach, Dewey Beach, Lewes, Bethany Beach, Millsboro and Milton, plus Fenwick Island, Ocean City and beyond. Out-of-town guests flying in? We meet flights at PHL and BWI too. Start With the Plan Not sure how many vehicles you need or when to book? Our wedding transportation planning guide walks through bridal party timing, guest shuttles and hotel pickups. Better yet, tell us your date and venues and we will sketch the plan with you: call (302) 644-0400 or contact us today. Peak spring... - Published: 2016-05-17 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/contact/ The Jolly Trolley Contact Us Make a Reservation We would love to hear from you! Please fill out the form to contact our offices about any questions or updates you may have, or for more information about the Jolly Trolley, our private transportation vehicles, and our shuttle services. Fill out my online form. Or Email Us Directly: General Inquiries Advertising Reservations Employment - Published: 2016-05-17 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/ Award Winning Professional Transportation Services - Exceeding Expectations Year Round - Rehoboth-Dewey Seasonal Shuttle Information Year-Round Reservations Weddings Airport Transit Night Out birthday Bachelor/bachelorette Bar/Bat Mitzvah Celebrations of life FIFA World Cup, Concerts & Sports Venues Proms/Homecoming Tours Local Events Non-Profit Events About The Jolly Trolley The World's Original Jolly Trolley since 1970 and your tour & transportation professionals in Southern Delaware & the Mid-Atlantic Region offering Reservations for Weddings, Airport Transfers & Black Car service, Special Events, Tours and much more! Our experienced, fully licensed and insured team is here to help with all of your upcoming ground travel plans utilizing decades of experience, modern technology systems, and proven quality control methods. Learn More Year-Round Services Learn More Seasonal Shuttle Learn More Corporate Services Learn More The Jolly Trolley Your Iconic Transportation Service Since 1970 Make a Reservation ## Posts - Published: 2026-04-08 - Modified: 2026-07-27 - URL: https://www.jollytrolley.com/how-to-plan-corporate-event-transportation-in-southern-delaware-a-checklist/ - Categories: Travel Tips A corporate event is judged on a hundred details, but transportation is the one everyone notices when it goes wrong. Attendees stuck at the airport, a keynote speaker circling for parking, half the team arriving at dinner twenty minutes late: these are the moments that undo months of planning. After more than three decades of moving companies around southern Delaware, from conference hotels in Rehoboth Beach to celebrations at Dogfish Head in Milton, here is the checklist we walk every event planner through. 1. Start with headcount and flow, not vehicles Before you think about buses, sketch the movement of your event: how many people, arriving from where, moving between which points, and when. A board retreat with eight executives is a different plan than a 200-person conference with attendees flying into three different airports. Map the arrival wave, the daily hotel-to-venue loop, the offsite dinner, and the departure crunch. The vehicle list falls out of that map naturally. 2. Plan airport arrivals early Most corporate groups reach the Delaware beaches through Philadelphia (PHL), Baltimore (BWI) or the Amtrak station in Wilmington, and each has different drive times and traffic patterns. Our guide to choosing the best airport for a Delaware beach trip breaks down the options. For events, the keys are collecting flight numbers ahead of time, grouping arrivals into pickup waves, and using flight tracking so a delayed connection adjusts the schedule instead of breaking it. Executives and VIPs typically ride private black car; arrival waves fill mini... - Published: 2026-03-12 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/choosing-a-delaware-beach-transportation-company/ - Categories: Travel Tips Booking transportation for a wedding, an airport run or a corporate event should be simple, but from the outside most companies look the same: a website, some photos of vehicles, a phone number. After more than five decades serving the Delaware beaches, we know exactly which differences matter when something goes sideways at 5pm on a summer Friday. Here is what we would check before booking any transportation company, ourselves included. 1. Licensing and insurance, in writing This is the least glamorous item and the most important one. Ask whether the operator is FMCSA and USDOT regulated, and specifically whether they hold interstate authority. Any trip that crosses a state line, which at the Delaware beaches means every PHL and BWI airport transfer and every Washington or Philadelphia day trip, legally requires it. Our charter service operates as Jolly Trolley Limousine Service LLC: FMCSA and USDOT regulated, interstate licensed and insured. A legitimate operator will not hesitate to confirm this; hesitation is your answer. 2. Real local experience Southern Delaware in summer is its own driving discipline. Route 1 between Rehoboth Beach and Dewey Beach crawls on weekends, the Bay Bridge can add an hour to a BWI run, and every venue from Lewes to Bethany Beach has its own loading quirks. We have been driving these roads since 1970, family owned and operated since 1992, and that experience is built into every schedule we quote. An out-of-area operator discovers these problems on your wedding day; a local one planned... - Published: 2026-01-26 - Modified: 2026-08-12 - URL: https://www.jollytrolley.com/delaware-wedding-transportation-guide/ - Categories: Travel Tips Your wedding day is one of the most important days of your life. Family and friends are traveling from near and far to celebrate with you, and there is so much to plan before the big day. Transportation is the piece that quietly holds the schedule together, and after hundreds of thousands of wedding trips across southern Delaware since 1992, we can tell you it rewards a little early planning. Here is how we walk every couple (or their wedding planner) through it. Start with three details Everything in your transportation plan flows from three things: the start and end times and locations of your ceremony and reception, the number of people who need a ride, and any special travel needs. Bring those to your first conversation with us and we will go to work to craft your customized transportation program. We have decades of working relationships with the major wedding venues and hotels in southern Delaware, so chances are we already know your venue's drop-off points, boarding quirks and timing. Wedding party transportation A wedding is not a wedding without the couple and their closest friends and family. A few questions settle the wedding party plan: Will the bridal party and groomsmen travel together, or is arriving separately the better choice? Do the girls need to be at the venue early for hair and makeup, or is arriving just before the ceremony more your style? Will you need transport for photos at a memorable location, either a first look... - Published: 2026-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/history-of-the-jolly-trolley/ - Categories: Travel Tips The Jolly Trolley and its bright, colorful vehicles are a local icon, a familiar sight between Rehoboth Beach and Dewey Beach every summer for more than five decades. But most riders do not know how it all started, who started it, or how a pizza legend and a sign boat fit into the story. Here is the history of Rehoboth Beach's original trolley. 1970: The original Jolly Trolley The original Jolly Trolley hit the road in 1970 as a tour service for residents and visitors in Rehoboth and Dewey Beach. Its first owners and operators were Mr. and Mrs. Rodgers, Dewey Beach residents who simply enjoyed showing newcomers around town. The trolley quickly became part of the scenery, even appearing on Rehoboth Beach postcards of the era. The Jolly Trolley on a Rehoboth Beach postcard, circa 1970. The Grotto Pizza years More than fifteen years later, the trolley caught the eye of another local legend. Dominick Pulieri, founder of Rehoboth Beach's iconic Grotto Pizza, purchased the Jolly Trolley in the late 1980s. Dominick saw its potential as a moving advertisement, since it was already a beloved attraction at the beaches. But he quickly discovered that growing a booming pizza business and running a transportation service at the same time was a lot to handle. 1991: A sign boat and a new family Enter David and Christine Hastings. In the early 1990s, Grotto Pizza advertised on a local sign boat called the Aatcos, fondly known as Ms. Aatcos, which the Hastings... - Published: 2026-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/day-trips-from-southern-delaware/ - Categories: Travel Tips One of the best things about living in or visiting the Delaware beaches is how much sits within a day's reach. Washington, Philadelphia and even New York City are all close enough for a day trip from southern Delaware, and some of the best outings never leave Sussex County at all. Here are the trips our drivers get asked about most, with honest notes on timing so you can plan a day that feels easy instead of rushed. Washington, DC Around two and a half to three hours from Rehoboth Beach, Washington makes a full but comfortable day. The Smithsonian museums are free, the monuments are walkable, and spring cherry blossom season is worth planning a trip around. December brings the holiday displays. The biggest headache of a DC day trip is parking, which is exactly why groups charter: everyone rides together, gets dropped at the door, and nobody circles the block. Philadelphia and Longwood Gardens Philadelphia is roughly two to two and a half hours north: Independence Hall, the Liberty Bell, world-class museums and a lunch stop at Reading Terminal Market make an easy itinerary. Just outside the city, Longwood Gardens in Kennett Square is one of the most popular Pennsylvania day trips we run, especially for garden clubs and senior groups. The conservatory and fountain shows are spectacular in summer, and A Longwood Christmas is a beloved holiday tradition. Art lovers can push a little farther to Grounds for Sculpture in New Jersey. New York City Yes, New... - Published: 2026-01-21 - Modified: 2026-07-28 - URL: https://www.jollytrolley.com/choosing-the-best-airport-for-your-delaware-beach-trip/ - Categories: Travel Tips Planning a trip to the Delaware beaches, or bringing family and guests in from out of town? The first decision is which airport to fly into. No major airport sits right at the beach, but several are within a comfortable drive of Rehoboth Beach, Dewey Beach, Lewes and Bethany Beach. The right choice depends on where you are staying, your flight options, and how much summer traffic you are willing to sit through. Our team has been driving these routes since 1970, so here is an honest local comparison. Philadelphia International Airport (PHL) PHL is the region's largest hub, with the widest choice of nonstop domestic and international routes. From the airport, the drive to Rehoboth Beach runs roughly two to two and a half hours, mostly straight down Route 1 through Delaware. Lewes and Milton are a few minutes closer, Bethany Beach a few minutes farther. Best for: international arrivals, travelers who want the most flight choices, and anyone connecting through a major hub. Watch out for: summer Friday and Sunday backups on Route 1 near the beach towns. Build in a cushion if you have a tight schedule. Ready to book the ride from Philadelphia? See our PHL airport car service page. Baltimore/Washington International Airport (BWI) BWI is a similar drive, about two to two and a half hours to Rehoboth Beach, coming across the Chesapeake Bay Bridge and down Route 404. It is a major base for low-cost carriers, so it often wins on fare price. Best...