Uncover 300 years of maritime and cultural heritage with a guided stroll through the Old Port.
2 hrs
Guided walking tour, Bakery treat
Stroll Portland’s working waterfront and cobblestoned Old Port with a guide who weaves 300 years of stories into every stop. Feel the salt air, admire Victorian architecture and finish with a bakery treat.
Wear comfortable walking shoes, dress for changeable Maine weather, and arrive at least 10 minutes early.
Due to preservation efforts the route includes uneven surfaces and steps, making it unsuitable for some mobility devices.
Tickets without tour insurance are non-refundable and tours run rain, snow, or shine. Tour insurance must be purchased during initial booking and cannot be added later.
Portland's historic streets limit full accessibility for wheelchairs or walkers.
Use a parking garage or lot; Custom House Square at 25 Pearl Street is the nearest.
Well-behaved dogs are welcome with advance notice noted in your booking.
Andy's Old Port Pub, 94 Commercial Street, Portland, ME 04101.
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