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.
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.
Options
Sunset Windjammer Cruise Along the Coast of Portland Maine
Reviews
128 reviews
Total reviews and rating from Viator & Tripadvisor
The crew was great, its a...
Katie S,
Oct 8, 2025
- Viator
5.00The crew was great, its a great sailing experience on beautifully restored sailboats. Sunset cruise was beautiful. Be sure to wear layers.
Wonderful experience! ...
Dan P,
Oct 4, 2025
- Viator
5.00Wonderful experience! Great views and crew! The sailboat was amazing and overall I'd recommend to anyone in the area.
Great Afternoon activity!
emily b,
Oct 4, 2025
- Viator
5.00The experience was exactly as described. We brought wine and cups. Crew was friendly and blankets were provided.
Sail Away
Kyle R,
Sep 29, 2025
- Viator
5.00Beautiful night to be sailing. Crew and captain were a joy ! Would do it again! Saw several lighthouses.
Sunset Views were stunning.
Kaitlyn V,
Sep 28, 2025
- Viator
5.00Chill and beautiful experience with fun and welcoming guides. The sunset cruise was a perfect anniversary celebration.
Related Experiences
Operated by Portland Schooner Co.