PORTLAND · MAINE
Portland's standouts, both coasts.
The 10 standout city tours of Portland, Maine. Old Port cobblestones, Eastern Promenade harbour views, hidden histories and Black-history walks — Maine's working waterfront the way a local would show you.
Old Port + 3 Maine lighthouses in 2 hours from Portland Beer Hub. Small-group van tour with views and history. $69.
“This was basically transportation to the 3 lighthouses with a little history. The tour we actually would have enjoyed more was already booked by the time we decided to go”
Vintage fire truck tour of Portland, Maine: 50-minute ride with waterfront and lighthouse views, live narration, Old Port shopping time, $45.
“Learned a lot of facts about Portland and saw a lot of the city - that’s all I have to say - stop asking me to”
Portland hidden histories walking tour with Dugan. Small-group, funny storytelling across Downtown, Old Port, and Commercial Street.
“Unfortunately I was unable to make to the tour due to immigration check in from the cruise. Unable to reschedule or obtain a refund. Tour guide did try to get me on your even late.”
Old Port Maine food tour with lunch, a small group walk, chowder and lobster roll tastings, plus dessert on Fore Street.
“Do not eat breakfast before starting this tour.”
2-hour Windjammer sail in Casco Bay from Portland Maine. BYO snacks and drinks on a historic schooner, see lighthouses and seals.
“The experience of sailing the waters of Portland as they did centuries ago was truly amazing. Sailing the water was so relaxing to the soul. Taking in the beauty of the harbor and bay from aboard the Timberwind can not be topped. The Captain and his crew were professional and polite. The check in tea”
Old Port Seafood Lovers walking lunch in Portland: lobster roll, chowder, beer, lobster-fishing stories, and a sweet finish.
“Ray was amazing. Extremely knowledgeable and personable. I’d do the tour again just for him. I learned so many new things regarding the history of food and Portland.”
Portland, Maine Black history walking tour with Dugan. Small group, iconic stops, Underground Railroad stories, and donation to Abyssinian Meeting House.
“Dugan was amazing with historical knowledge and the ability to answer questions appropriately. Recommend this as a must do. If it is in the colder season layer and bundle up because you will want to give your full attention.”
Sail a historic schooner through Casco Bay on a Portland, Maine sunset cruise. Bring your own snacks and drinks for 2 hours.
“Even though it was a very foggy night, the sun still peaked through and we really enjoyed the views on the sailboat. We made some friends along the way and really enjoyed talking to the crew! Highly recommend you do this awesome experience.”
A 90-minute afternoon lighthouse cruise from Portland, Maine with Casco Bay wildlife, classic lights, and Fort Gorges views. Bring snacks.
“We had such a great time! The captain and Nash were very knowledgeable and friendly. It was great to get out on the water and learn about lobstering, the history of the area and lighthouses, and see so much wildlife. Highly recommend. Very fun!”
A self-guided audio walk through Portland’s Old Port with standout history stops, easy pacing, and great value at about $7.75.
“Nice walking tour that provides some history. I like that it isn't too long and helps you get oriented to the Old Wharf area.”
