Top 8 luxury & private 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. Private e-bike tour of Portland, Maine

Five hours through Portland's coastal scenery by e-bike — explore Old Port, enjoy a lobster roll, and take in views from iconic lighthouses.

3. Private sunset charter on a vintage lobster boat in Casco Bay

Two-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

4. Private vintage lobster boat cruise in Casco Bay

Two-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

5. Private boat tour to Fort Scammel in Casco Bay

Two to three hours aboard the Elizabeth Grace — explore historic Fort Scammel and enjoy views of lighthouses in Portland Harbor.

“This was an excellent trip from start to finish. Our guides and the boat captain were fantastic and had a lot of knowledge. I would highly recommend this experience.”— chrisjZ9090KE

6. Private lighthouses and Kennebunkport tour from Portland

Six hours in a comfortable vehicle — explore Portland's sites and South Portland lighthouses, including Portland Headlight, then visit historic Kennebunkport.

“Our day with Don, our private tour guide, was fantastic. He surpassed our hopes for a beautiful experience in coastal Maine. As a lifelong resident, Don shared incredible insights into the area's history and geography, along with personal stories. His knowledge of local tales, like those of York and its lighthouse, added depth to our tour, including the story of the baby taken to the lighthouse and details about the Bush Compound and Churchill. Lunch at Barnacle Billy’s was a highlight, featuring excellent lobster rolls, great service, cold draft beers, and a wonderful atmosphere. Our table offered a stunning waterfront view, just five minutes from downtown Ogunquit. We also enjoyed time to shop in Kennebunkport, marveling at the beautiful architecture, including the famous wedding cake house, and we visited both York and Kennebunk. Spending the day with Don was truly enjoyable. It was a fabulous experience.”— ginnys237

7. Afternoon lighthouse cruise in Portland Harbor

Two hours on the Elizabeth Grace — a scenic cruise of lighthouses, historic forts, and islands with local drinks included.

“The boat ride was wonderful, offering stunning views of several lighthouses. The city's skyline from the water was breathtaking. We felt very comfortable aboard the small boat. Our captain was friendly, and the deckhand provided a warm welcome and great insights. We are happy we included this experience in our plans.”— Kate_W

8. Sunset boat cruise in Portland Harbor with local drinks

One and a half hours on the Elizabeth Grace — local craft beer as you enjoy sunset views over Portland Harbor and explore Casco Bay's lighthouses and islands.

“The sunset boat ride was wonderful. The captain and crew were excellent. I enjoyed the location, the sights, and the historical context. We even spotted seals, which was a delightful bonus. I highly recommend it.”— Margaret_L