Year Round Services

Special Events & Occasions

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For life's biggest moments our professional charter 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 will recommend the JT to anyone looking for an authentic Rehoboth Beach experience. Thank you JT!!"

- Kathy

"We booked the Jolly Trolley for my Bachelorette Party to transport us from South Bethany to Dewey. The ability to use the Jolly Trolley for short blocks of time was what initially sold me. I didn't want to pay for a driver for 7+ hours out when we only needed drop off/pick up and I couldn't find any other transport service that made that as easy as the Jolly Trolley! They're drop off/pick up system makes so much sense. Our drivers were absolutely wonderful. They both were so kind, communicative and easy to work with. They even upgraded our transportation one way at no additional cost AND when we finished the evening a little earlier than expected, our driver picked us up a bit early. We would gladly use the Jolly Trolley again! Thank you Lydia and Jim!! "

- Dawn D.

We recently went down to Rehoboth for a girls weekend and used Jolly Trolley for our transportation to and from Dewey. Booking was super easy thanks to Lydia and they were very responsive and flexible to any changes we had. Our driver, Will Y, was THE BEST and truly was the topper on a great day for some long over due fun where we could finally let lose and not have to worry about a thing! Highly recommend Jolly Trolley and will absolutely be using them again!!!

Anna L.

Many thanks for hundreds of Jolly Trolley rides during my 34 years as a Dewey Beach resident. For a memorable / unique birthday gift, I arranged a Jolly Trolley tour with owner Christine Hastings as our tour guide. Christine's pleasant personality, excellent customer service skills, and incredible history of this area made it extra special. Treat yourself and others to a trolley ride. It's part of the beach culture our family and friends treasure year after year. It's much more than transportation... It's at the top of the Must-Do list.... the ultimate beach experience. With appreciation to our community's Jolly drivers and the Hastings Family

- Jeanine O.

"Most folks would not think about hiring Jolly Trolly for a funeral, but I did just that.  My husband’s funeral was in July in Rehoboth and his celebration was in Lewes at Irish Eyes.  The thought of hundreds of people, so many from out of town, trying to navigate traffic between the two spots was a nightmare.  My first thought was Jolly Trolly, being a local and knowing they do weddings and other celebrations.  From the first call the entire team was beyond amazing.  We had several vehicles running back and forth to and from the service and they coordinated beautifully with Parsells Funeral Home to make sure nobody was late or left behind.  I could not be more grateful for the kind, caring, professional and exceptional service from the drivers and all involved.  Thank you Jolly Trolly for making this happen!!  As a local small business owner, it meant so much to deal with a family run and local company.  I recommend you to anybody who needs transportation for any reason. "

- Dianne D.

My family has used the Jolly Trolley in a variety of ways in the 14 years we have lived at the beach. JT has provided safe, reliable transportation to and from the Cape prom, Dewey Beach, and while Christmas caroling around Rehoboth. The staff, especially Christine Hastings, has always been nothing but courteous, caring and concerned for our safety. The Jolly Trolley is a fabulous resource for visitors and residents alike. Thank-you, Hastings family, for being here.

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