11. Portland Lighthouse Boat Cruise with Oysters and Prosecco
5.0· 5 reviews· 1.5 hoursTwo-hour cruise from Portland Beer Hub with oysters and prosecco served on Casco Bay, enjoying coastal views and culinary delights.
“The Oysters and Prosecco experience was fantastic. The oysters were incredible, and the crew on the small boat made it enjoyable and intimate. I highly recommend it.”— baileyh927
22. Private sunset charter on a vintage lobster boat in Casco Bay
5.0· 40 reviews· 2 hoursTwo-hour private charter on a vintage lobster boat — sunset views, iconic lighthouses, and first round of drinks included.
“We had an incredible experience. My family and I spent our second leg of the Maine vacation near Portland and arranged a private sunset cruise with a chef as a surprise for our mom. It truly became a highlight of our trip. We were fortunate to enjoy excellent weather. The captain skillfully guided us through the bay without any sea sickness, while our hostess was fantastic at answering all our questions and sharing insights about this stunning area. However, the star of the show was our chef, who prepared the most delicious meals in a very small area. If you're on the fence about booking this cruise—or, I suspect, any of their offerings—don’t hesitate. Our family had a fantastic experience, and if we ever find ourselves in the region again, we would certainly book another cruise. It was the perfect way to conclude a memorable vacation on our second to last night.”— Christine23140
33. Private vintage lobster boat cruise in Casco Bay
4.8· 65 reviews· 2 hoursTwo-hour private sightseeing cruise from Portland, visiting four lighthouses with complimentary drinks included.
“This experience was a scam. I was notified just 15 minutes before the scheduled time that they had "engine trouble" and canceled. It cost $380 per person or $740 for a group of six, and it seems they just didn't want to proceed.”— Allen_C
44. Portland lighthouse bicycle tour with lunch from a local food truck
4.8· 151 reviews· 5 hoursThree hours cycling tour of Portland’s coastline, visiting four lighthouses and enjoying an XL lobster roll from the award-winning Bite into Maine food truck.
“This was my second time on this must-do tour. The guides are fantastic, the riding is smooth, and the scenery is unforgettable. The lobster rolls are outstanding.”— Sightseer38831662407
55. Culinary walking tour of Portland's Old Port
4.8· 426 reviewsThree hours through Portland's Old Port — taste Maine-inspired fare from 4-5 venues, including a sweet treat to finish.
“Book this tour with Ray during your next visit to Portland. It was the highlight of my birthday experience. Ray shared so much knowledge, and we truly loved all the delicious food.”— Betsybbbbb
66. Walking food tour of Portland — donuts and city history
4.8· 190 reviews· 1.8 hoursTwo hours on foot — taste local donuts at The Holy Donut and other top spots, plus insights into Portland's history.
“Fantastic tour with delicious doughnuts included! Kris was an outstanding guide, filled with knowledge about Portland's history and interesting anecdotes (some amusingly questionable). I had a wonderful experience!”— David B
77. Lighthouse cruise along Portland's coastline
4.8· 58 reviews· 1.5 hoursNinety minutes on a classic 39' boat — scenic views of lighthouses, seals, and seabirds in Casco Bay, with options to bring your own picnic.
“I had an excellent experience; both the captain and first mate were well-informed about the area and kept us entertained throughout the trip.”— Hunter_T
88. Walking lunch tour of Old Port's seafood scene in Portland
4.8· 148 reviews· 3 hours1.5-mile stroll through Portland's Old Port, featuring a classic Maine lunch with lobster roll, chowder, local beer, and surprise tastings.
“Ray was exceptional—very knowledgeable and friendly. I would gladly take the tour again just for him. I discovered a lot of fascinating information about the history of food and Portland.”— Teesha_G
99. Two-hour sunset Windjammer sail in Casco Bay, Portland
4.8· 144 reviews· 2 hoursTwo hours sailing aboard a historic wooden schooner — enjoy the rugged Casco Bay coastline with views of lighthouses and marine life.
“This was the most enjoyable sailing experience I've ever had. The crew was fantastic, and the atmosphere was incredibly relaxing. Time flew by; we wished it could have lasted longer. The price was excellent, especially considering the stunning views.”— bethbI9226TJ
1010. Two-hour Windjammer cruise in Casco Bay, Portland
4.6· 186 reviews· 2 hoursTwo hours on a historic wooden schooner — sail through Casco Bay, watch for seals, seabirds, and lighthouses, with room to pack your own meal and drinks.
“It was quite chilly for most of the trip, but the views were stunning. We spotted a few seals and gained more knowledge about Portland. Overall, it was a fantastic experience.”— carriemL7291VM
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