Top 7 adventure things to do in Portland

1. Private yacht cruise around Casco Bay in Portland

Two, four, or six-hour private powerboat cruise — explore iconic lighthouses and marine wildlife, swim, and enjoy the coastline at your own pace.

2. Portland Lighthouse Boat Cruise with Oysters and Prosecco

Two-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

3. Sunset sea kayak tour in Casco Bay

Two hours of kayaking on Casco Bay — enjoy the sunset views with a guided trip suited for all skill levels.

“Tom was an excellent guide who effectively taught the less experienced kayakers in our group. The weather was wonderful, contributing to an unforgettable sunset.”— Joseph_J

4. Lighthouse cruise along Portland's coastline

Ninety 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

5. Two-hour sunset Windjammer sail in Casco Bay, Portland

Two 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

6. Two-hour Windjammer cruise in Casco Bay, Portland

Two 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

7. Whale watching tour from Portland, Maine

Three to four hours, on a comfortable vessel — spot humpback, fin, and minke whales along the rugged coastline with expert naturalist guidance.

“Understanding that whales are wild animals, we were thrilled to see two Fin Tail whales, with one nearly 100 yards from our boat at the season's end. Coming from a coastal town, I felt prepared for offshore conditions. We were fortunate with calm seas of 1-2 feet. The guides were respectful and knowledgeable. While the boat was somewhat small, this was clearly a whale watching trip rather than a leisure cruise. Embrace the adventure!”— Q2475SUlisar