Sip local flavors and uncover Portland stories aboard a guided trolley
Tastings, snacks, chocolate truffle
Ride through Portland’s craft beverage scene with guided stories, waterfront views, and stops at local favorites. Pair the city’s prohibition-era past with an after-hours tasting experience.
All sales are final. This tour may be cancelled if the minimum number of passengers is not met.
Customer parking is not available at Portland Discovery. Allow extra time for downtown parking; nearby public options include Ocean Gateway Lot, Angelo’s Acre Lot, and Simba Parking Lot, a 7- to 20-minute walk from the ticket booth.
The trolleys are heated and can stay warm, but they do not have air conditioning. Open windows provide a breeze while the trolley is moving.
Portland Discovery, 170 Commercial Street, Portland
The guides here really make or break the experience, and fortunately most travelers rave about their personalities and expertise. Tyler brings Portland's history to life on walking tours, while AJ wins people over with her humor and local recommendations. Ray and Timothy both get praise for their knowledge and storytelling abilities, though opinions vary on pacing. The oyster and bubbles boat tour sounds particularly special, with a master shucker guiding you through Portland's oyster scene. Tours cover both Portland and Bar Harbor locations, with options ranging from history walks to culinary experiences. Food portions generally satisfy guests, with most leaving pleasantly full from stops featuring lobster rolls, chowder, and other Maine staples. A few travelers felt the tours spent too much time on guide monologues rather than diving into building histories or meeting restaurant owners. The occasional complaint surfaces about pacing or wanting more variety in stops. Overall though, visitors appreciate getting a solid introduction to Portland's food scene and Old Port area, especially from guides who clearly love their city and know where locals actually eat.
My fiancé and I did the food tour with Randy and it was so much fun!! Easily one of our favorite things we did on our trip. We were able to taste a wide variety of what Bar Harbor had to offer us and get a little history with it as well!! Highly recommend Maine Day Ventures food tour!
Mabel Zwenger
July 1, 2026
My fiancé and I did the food tour with Randy and it was so much fun!! Easily one of our favorite things we did on our trip. We were able to taste a wide variety of what Bar Harbor had to offer us and get a little history with it as well!! Highly recommend Maine Day Ventures food tour!
Mabel Zwenger
July 1, 2026