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.
“Beautiful views of Portland and all the lighthouses! Your guide was wonderful and very informative about all the different places we visited.”
Sail a historic schooner through Casco Bay on a Portland, Maine sunset cruise. Bring your own snacks and drinks for 2 hours.
“Fantastic crew, beautiful weather even if windless….helped create the most peaceful glassy water…it is a must do!”
Small-group Portland Maine sunset lighthouse cruise on Casco Bay with local craft drinks, views of Fort Gorges, Portland Head Light, and Peaks Island.
“one word- AMAZING! the lighthouses were incredible, we even got to see a good amount of seals either perched up on a big rock or in the water swimming!! 100% recommend and would definitely do again!!”
Sunset sea kayaking on Casco Bay from Portland: small-group tour with gear and dry bag, seals, wharves, and distant lighthouses.
“Such an amazing way to experience Portland! Guides are knowledgeable and offer local insights into the city. I will say it was pretty physical, my friend and I are both in our mid twenties with no physical impairments and definitely felt like we got a good workout in. Just keep that in mind but if…”
A 3.5-hour sunset shuttle through six Gorge waterfalls, with reserved Multnomah parking, short hikes, and Crown Point sunset views for $99.
“Our tour guide, Branden, was AMAZING! We were lucky enough to be on a very small tour, only our family of 4 & one other couple. Branden’s passion for everything Columbia River Gorge was infectious. My 19-year-old son & 13-year-old daughter totally bought into the tour & listened attentively. Braden knew EVERYTHING about the geology,…”
Private sunset cruise on a vintage lobster boat in Casco Bay with drinks, onboard comfort, and guided lighthouse history.
“This experience was amazing! We just got married and this was the first time where we just got to sit back and relax since the wedding. Captain Zach and Deckhand Lauren were incredible! They showed us all the lighthouses and were knowledgeable! They answered all our questions. We really enjoyed our time with each other…”
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.
“Very relaxed and fun, don't forget to bring food and drink! It is a little crowded but not bad. Good for family or a couple, I wouldn't go with your friend(s).”
Private sunset boat tour around Portland and Casco Bay with Captain Kevin and Sarah, Portland Head Light views, and comfy blankets.
“Kevin and Sarah showed us a great time on our boat trip. The vessel was in excellent condition and we thoroughly enjoyed the outing. We visited with several islands off the mainland.”
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…”
