PORTLAND
Portland's standouts, both coasts.
The 10 standout evening experiences a Portland traveller will actually book. What each one covers, who runs it, and what it costs from the dock or the trailhead.
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.”
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!”
Sunset sea kayaking on Casco Bay from Portland: small-group tour with gear and dry bag, seals, wharves, and distant lighthouses.
“This was a wonderful, memorable trip. We are not kayakers, but our guide, Joe’s, love of the the water was infectious. He shared many interesting stories regarding the history of Portland’s harbor. The staff provides all the gear, and you will get a quick lesson and tips. Then you are on the water. Great fun.”
A 3.5-hour sunset shuttle through six Gorge waterfalls, with reserved Multnomah parking, short hikes, and Crown Point sunset views for $99.
“Great tour and our guide James was very knowledgeable. I was able to complete the tour despite some snags in the schedule. Portland Falls is a must see. Hope to do this tour sometime in the summer when it is less cold.”
Private sunset cruise on a vintage lobster boat in Casco Bay with drinks, onboard comfort, and guided lighthouse history.
“It was an outstanding tour! First mate and Captain were the best. Very scenic tour and relaxing. Highly recommend it. Score big points with your date.”
A $33, 90-minute Portland night walk linking 9 haunted spots, short stops, and a live guide. Starts at 10:30pm near transit.
“It was a great experience very cool kid friendly and very informative I would do it again if possible”
Casco Bay sunset cruise on the Ruth: 4 Maine lighthouses, seals, seabirds, Fort Gorges views. Bring your own food or wine.
“An amazing evening on the water of history and scenery. Would highly recommend this to anyone. Barrett, the Captain and Nico the first mate were well informed on all the sites and did a great job. Bring your own wine and or food.”
Private sunset boat tour around Portland and Casco Bay with Captain Kevin and Sarah, Portland Head Light views, and comfy blankets.
“We had a fun afternoon seeing the islands of Casco Bay. Kevin and Sarah provided a fun, relaxed time and expertly showed us many scenic views. Near the end, we visited a great restaurant for food and drinks then ended the trip right at dusk when the light turned golden.”
Private 2-hour Willamette River sunset cruise in Portland with a USCG-licensed captain, bridge views, White Stag sign, and BYOB.
“A lovely time on the river in covered (pontoon style?) boat. Nice seating. We took our own snacks. 5:00 PM tour in summer sunset is prolly 7 or 7:30. If you want to see the sunset and city lights go later. It was bright and clear our whole trip and didn’t rain. Would do it…”
