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 we will help you build an itinerary that works that day.
Wine Tours
Prefer grapes to grain? We run winery-focused afternoons pairing Nassau Valley and Salted Vines with a lunch stop in Lewes or Bethany, and we can mix one winery into a brewery day for the split-preference group. Wine tours are a favorite for birthdays, girls' weekends and anniversary trips.
Milton Brewery Tours
Milton deserves its own itinerary. Beer travelers fly in from around the country for Dogfish Head, and we have been driving those pilgrims for years, including transportation for corporate events at the brewery itself. A classic Milton day pairs the brewery with lunch in Milton's historic downtown and a stop or two heading back toward Lewes or Rehoboth. Staying in town? Our Milton car service covers the pickups.
Who Books These Tours
- Bachelor and bachelorette parties: the classic beach-week brewery crawl; see our bachelor and bachelorette transportation.
- Birthdays and celebrations: a trolley full of your favorite people; see birthday transportation.
- Corporate outings: team afternoons and client entertainment through our corporate services.
- Reunions and wedding weekends: a ready-made group activity the day before or after the big event.
Why Tour with Jolly Trolley
- The designated driver is built in: professional, licensed chauffeurs, FMCSA and USDOT regulated.
- Vehicles worth photographing: classic trolleys, plus black cars, mini buses and full buses in our fleet.
- Actually local: serving the Delaware beaches since 1970, so our route suggestions come from experience, not a listicle.
- More than breweries: we also run customized day tours, from Washington DC trips to local history rides.
Book Your Brewery or Wine Tour
Call (302) 644-0400 or request a reservation online with your date, group size and must-visit stops. Summer Saturdays and fall festival weekends book out early.