Top 10 cultural & heritage 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. Lighthouse bicycle tour along South Portland's greenbelt

Two hours cycling through South Portland — visiting Portland Breakwater Light and Spring Point Ledge Light along the scenic Greenbelt Pathway.

“I arranged a 2-hour guided tour for myself and five friends and family members while our cruise stopped in Portland, Maine. Although I preferred the longer tour, we opted for the shorter one since some hadn’t ridden bikes in a while. Everyone enjoyed themselves, with one person declaring it the highlight of her trip. The ride was easy-going, featuring gentle climbs and mostly flat paths that meandered through parks and picturesque spots. Our guide, Ian, maintained a relaxed pace that suited everyone and skillfully navigated intersections and traffic zones. He provided insights on historical, geological, and local points of interest, engaging with us during the ride to answer questions and highlight key features. His laid-back demeanor and knowledge of Portland's history were well-received. We visited the two advertised lighthouses and also glimpsed the Portland Head Lighthouse from a distance, along with wetlands, Civil War fort structures, and a memorial for Victory ships built in Portland during World War II. Ian allowed ample time at key locations. The total distance was precisely 7 miles, and it felt swift. I highly recommend this tour and look forward to returning for the longer option.”— Don_W

4. Guided walking tour of Portland's hidden histories

Two hours of storytelling on a 1.5-mile route through Old Port, focusing on diverse narratives and local history with a knowledgeable guide.

“This was undoubtedly the best walking tour I have experienced. Dugan, our guide and owner, impressed us with his extensive knowledge of Portland's history. He was entertaining and engaging, adept at addressing our group's interests and answering every query while providing both historical and geographical context. I wholeheartedly recommend this tour.”— MTeatum

5. Historical tour of Portland and three lighthouses

One hour and 45 minutes by minibus — see Portland's highlights and three lighthouses with a local guide sharing insider knowledge throughout the tour.

“Derek provided excellent guidance and shared a valuable local perspective on Portland. The lighthouses are truly a sight to behold.”— Kent_P

6. 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

7. 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

8. 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

9. 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

10. Portland lighthouse bicycle tour with lunch from a local food truck

Three 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