Year Round Services

Weddings

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 and fall Saturdays book out 6-12 months ahead.

Travel with the Best!

Jolly Trolley was voted Best Delaware Wedding Transportation - Downstate by Delaware Today in 2026!

Wedding Transport Planning Tips

Testimonials

Hear From Our Clients

- Terry F.

"I wanted to let you know that your company was amazing to work with for my daughter’s wedding on 10/28. From first contact with Debra back in May through the end of the evening when the bus dropped our guests back at the hotel. The bride and groom said they’re driver was SO nice and the people who rode the bus said the driver was amazing and that there was singing and the whole atmosphere was just wonderful!! I am a very organized person and I absolutely loved how organized everything was down to receiving the trip manifest with every single bit of information!! It gave me such a sense of peace and calm that everything would indeed be perfect on that day!! I will 100% recommend your company to anyone looking for a charter, my experience was amazing!!! Thank you so much for such a wonderful experience!!!"

- Roberta D.

"I just wanted to take a moment to express my gratitude to you and Jolly Trolley for your help with coordinating transportation of our daughter and now son in law's wedding on October 6, 2024. Your knowledge and assistance of the area, routes and hotels as well with any questions/changes that I had was very reassuring along the way. As promised, all vehicles showed up on time as scheduled. It was very helpful that you shared names, phone numbers, of driver names, phone numbers, etc. for the actual day, should there have been any hiccups, but there were not! Again, thank you so much, it was a pleasure working with you and I would recommend you and Jolly Trolley to any of our friends in need of chartered transportation service in the future."

- Cecilia W

Where do I even begin? My husband and I had a two-year engagement, but knowing how busy October is here in Rehoboth, transportation was at the top of our to-do list. If you're getting married in Rehoboth or Dewey Beach, what better way to get around than the Jolly Trolley!?

We had the Trolley for our bridal party all day and night, and for our guests after the ceremony to the reception. They also picked everyone up at the end of the night. Our guests LOVED not having to worry about transportation, and the Trolley team made everything easy breezy!

The communication between me and the Trolley team was outstanding — they had an answer for every question I had. I would recommend the Jolly Trolley to anyone and everyone planning an event in the area! It's such a fun way to travel and arrive in style!

- Dana F.

Wedding Planner

"I highly recommend Jolly Trolley for any wedding or group transportation. They are a pleasure to work with and consistently provide excellent service. I've worked with them more times than I can count, and they have always taken great care of my clients, so I rarely use anyone else. We love working with the team at Jolly Trolley!"

- Anna L.

"The Jolly Trolley was just the perfect transportation for our wedding guests. From the initial conversation to the night of, everyone we interacted with were very professional and kind throughout. Our drivers were incredibly patient with us as plans changed. The drivers really went above and beyond! We are so happy that they were a part of our day. Thank you again Jolly Trolley!!!"

- Maria

"Jolly Trolley was incredible to work with from start to finish. Easy to book, reliable, great customer service, and our shuttle arrived on time! Highly recommend "

- Nancy

"Want to let you know that everything went smoothly for our wedding at the Indian River Life Saving Station this past Saturday. The trolley and bus were on time and our wedding guests had a great time. Your drivers were terrific.

Thank you for everything and all the best"