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.
Product ID: 9EQF7F
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.
Pete was a great guide. Very knowlegeable and the food was fantastic.
Madison Miller
August 30, 2026
Pete was a great guide. Very knowlegeable and the food was fantastic.
Madison Miller
August 30, 2026
Trace Portland's ghost stories and history on a private lantern-lit walk
Cruise Casco Bay with waterfront narration and a local drink included
Pair fresh oysters and prosecco with Portland coastal views
Sail into dusk with Casco Bay views, landmark narration, and a local drink
Pair Portland history with local beer on a guided Old Port stroll