PORTLAND
Portland's standouts, both coasts.
The 10 standout walking tours a Portland traveller will actually book. What each one covers, who runs it, and what it costs from the dock or the trailhead.
Walk Portland’s donut scene with a local guide, tasting at shops and ending at Voodoo. Vegan and gluten-free options.
“Great tour! Donuts and wonderful info about Portland!! Did I mention donuts ?? Kayla was an amazing guide.”
Portland hidden histories walking tour with Dugan. Small-group, funny storytelling across Downtown, Old Port, and Commercial Street.
“This is a MUST DO experience. Our daughter had recommended it to us after she participated in this excursion as part of a bachelorette weekend! Dugan is a gifted orator and shares an abundance of knowledge regarding the history of Portland, Maine which spans over centuries. BTW—there are many surprises along the way as well!”
A 2-hour Portland Maine walking tour with a local guide, small groups, and included snacks. See Old Port lobster sites and more.
“Anne was very knowledgeable about history of Portland. The tour was informative and fun at the same time.”
Old Port Maine food tour with lunch, a small group walk, chowder and lobster roll tastings, plus dessert on Fore Street.
“Having just done a food tour in Boston a few days prior, I was excited to hear about the Portland food scene! While the history and background of the wharf area was interesting, our guide (Timothy) seemed more interested in pushing his personal art business than providing quality food options. The first stop, fish tacos,…”
A 2–2.5 hour small-group walk through downtown Portland’s parks, architecture, and public squares with a certified local guide for $29.
“Kind and intelligent guide, architecturally beautiful city, lots to see! Be sure to check out Voodoo doughnuts and Powell's book store afterwards. It’s totally worth it xD”
Portland walking food tour with Holy Donut skip-line stops, six Maine donut samples, and local history on a scenic Old Port walk.
“This tour was so fun and the donuts were amazing! Our guide Chris gave us so many fun facts and showed us the highlights”
Old Port Seafood Lovers walking lunch in Portland: lobster roll, chowder, beer, lobster-fishing stories, and a sweet finish.
“Everything was wonderful, from the guide to the food!! Definitely recommend this tour for you!! It will not disappoint.”
Portland, Maine Black history walking tour with Dugan. Small group, iconic stops, Underground Railroad stories, and donation to Abyssinian Meeting House.
“The tour is weaved through the streets of Portland and thanks to the In-depth research which the tour guide has done, it brings history to life through landmarks and visuals!”
Four Portland pizza styles, four full slices, a ~1-mile walk in about 2 hours, with local guide Beau and neighborhood food tips for $75.
“A surprisingly diverse variety of pizzas. And I’m from New York so I thought I knew pizza 😆 it was fun to try the variety. And walking between stops gave me just enough time to stretch and breathe a bit between slices. The tour guide Beau was excellent, and very knowledgeable about both pizza and…”
A self-guided audio walk through Portland’s Old Port with standout history stops, easy pacing, and great value at about $7.75.
“Our first walking tour. The did such a good job. We look forward to doing more tours like it. Directions were easy to follow and it was interesting”
