Sunset Windjammer Cruise Along the Coast of Portland Maine

Overview

2 hours

Mobile ticket

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds.

(NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites).

All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Additional Info

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Suitable for all physical fitness levels

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What‘s Included

Environmentally friendly marine composting toilet

Life jackets for adults and children

2 Hour Cruise

Food and drink—But feel free to bring your own!

Gratuities

Group Narration - Our captain and crew are happy to answer questions about the harbor sights!

What To Expect

Casco Bay

Enjoy the beauty of the rugged coastline, complete with lighthouses and seals, as we slip through the pristine waters of Casco Bay.

Admission Not Applicable

See the gorgeous skyline of Portland, Maine's largest city which was established in 1786. Observe Portland's working waterfront as fishing boats depart and return to the wharves that form the heart of Portland and are home to local businesses that have been passed down for generations.

Admission Not Applicable

Options

Sunset Windjammer Cruise Along the Coast of Portland Maine

Reviews

4.81

113 reviews

Total reviews and rating from Viator & Tripadvisor

102

Lovely experience !
Kristine G,
Sep 17, 2025
- Viator
5.00
Be right on time -the crew is prompt ! We had a great time and enjoyed our own bottle of wine , which was a great option !
Absolutely beautiful and...
Amy S,
Sep 15, 2025
- Viator
5.00
Absolutely beautiful and peaceful sail....it was perfect...crew were professional and knowledgeable. Thank you
Sunset cruise
Joey M,
Sep 14, 2025
- Viator
5.00
Beautiful evening sunset cruise of the Portland, Maine coast. The staff was very attentive and made sure we had a great experience.
Lovely boating activity!
sarahtownswick,
Aug 31, 2025
- Viator
5.00
Had a gorgeous sunset cruise with An experienced staff and friendly people. Couldn’t recommend enough!
Great experience for...
Chandria M,
Aug 29, 2025
- Viator
5.00
Great experience for being our first time on a sail boat! It was relaxing and a wonderful way to see Casco Bay from the water.