Top 8 kids-friendly 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 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

3. 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

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. Vintage fire truck sightseeing tour in Portland

Fifty minutes on a vintage fire engine — explore Portland’s history with a guide and see lighthouses, Civil War forts, and iconic parks.

“This is a brief and efficient tour that offers a fantastic view of the downtown area. The staff is welcoming, and blankets are provided if the weather gets chilly.”— Jimmie_M

6. 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

7. 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

8. 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