PORTLAND
Portland's standouts, both coasts.
The 10 standout cruises & boat tours a Portland traveller will actually book. What each one covers, who runs it, and what it costs from the dock or the trailhead.
A 1 hour 45 minute Portland Harbor cruise with Casco Bay lighthouses, Civil War forts, and big water views for $54.
“Very informative. Great way to learn about the general area and history. Crew was friendly and knowledgeable. Beautiful views of lighthouses and city.”
A 2.5-hour Portland Willamette River dinner cruise with live piano, a 3-course local meal, and bridge-by-bridge city lights views.
“Food, atmosphere and all over experience was great! The food was perfect and the wait staff paid great attention to detail. It wasn't too crowded so you could enjoy conversation with others!”
A 2-hour Willamette River lunch cruise in Portland with live piano, reserved seating, and bridge-by-bridge landmark narration for $88.
“Best experience ever, viwing the wonderful Portland bridges and a great lunch served!. It was really worth it.”
One hour on Portland Harbor seeing four lighthouses and Fort Gorges, with onboard snacks, restrooms, and fun, clear history for $39.
“Honestly I bet it would have been a great experience. I drove up from RI and got there about a minute late. Coming from out of town I wasn’t sure about parking and then found the parking lot. Then I had to try figuring out which ship was the one I was supposed to be…”
Sail Casco Bay from Portland on a historic Maine windjammer. Bring snacks and drinks, enjoy 2 calm hours, and maybe help with sails.
“Lovely experience wandering the harbor. Had a mid afternoon flight. Do the perfect am activity. Staff was lovely”
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”
Casco Bay sunset from Portland. See Maine lighthouses, hear WWII shipyard stories, and watch for seals and dolphins. 1h45, $56.
“This was an amazing experience. All that we previously learned/experienced via land was great, but experiencing Portland from the water at sunset was truly unforgettable. Tour guide/captain very knowledge and personable. I would do this again in a heartbeat!”
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 1.5-hour Willamette River happy hour cruise in Portland with captain narration, major bridges, and buy-on-board snacks and drinks.
“This was a great way to see the bridges and the city. The staff is amazing! Truly enjoyed this experience ❤️”
Small-group Portland Maine sunset lighthouse cruise on Casco Bay with local craft drinks, views of Fort Gorges, Portland Head Light, and Peaks Island.
“The Portland beer club is a fantastic meet up spot where we met Christopher- he is such a gem that we decided to go back after the boat ride for a round of beer and cider. Denny and the captain were super warm and knowledgeable about the history. Highly reccomend this company and the tour!”
