Top 10 water & beach 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. 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

4. 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

5. Maine lighthouse tour from Portland

Three-hour tour of Maine's scenic coastline — visit three historic lighthouses with opportunities for close-up views and exploration of their architectural details.

“This tour showcased some fascinating sights, and our local guide was both informative and friendly. I highly recommend it.”— Terence_M

6. 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

7. 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

8. 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

9. 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

10. Sunset cruise around lighthouses in Casco Bay

A 105-minute fully narrated cruise through Casco Bay's lighthouses and islands, showcasing evening breezes and city lights.

“Experiencing Portland from the water at sunset was truly unforgettable. Everything we had learned and encountered on land was great, but this was an extraordinary experience. The tour guide and captain were knowledgeable and friendly. I would definitely do it again!”— Jayne_V