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
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
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!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
147 reviews
Total reviews and rating from Viator & Tripadvisor
Fun excursions on the harbor on a historic ship.
James M,Jun 5, 2026
- Review from Viator
5.00The crew is friendly and professional. The boat is over 100 years old and completely seaworthy. If I could have afforded it, I think that a four hour cruise would have been perfect.
Lived our first sail experience with Windjammer!
RachaelLeissner,Jun 4, 2026
- Review from Tripadvisor
5.00We decided last minute to do a sunset sail and picked the best one! Had an amazing time, adventurous at times, relaxing at times, and we just had a blast! Loved the crew and captain as well as the views you never get to see of the sites, the view from the water looking to land! Stunning.
Great scenery, but very cold and uncomfortable.
Ray S,Nov 1, 2025
- Review from Viator
3.00It was EXTREMELY COLD! I wish there had been seats. The seating situation wasn't comfortable at all. The scenery was nice.
Great boat, fun trip
jasonbI3745UK,Nov 1, 2025
- Review from Tripadvisor
4.00Great boat, nice folks. The fall views were amazing. No real seats so be ready to sit on the center of the boat. I would recommend bringing a seat pad. They don’t provide drinks or do any tour guide taking.
A must do for beautiful memories
Cecily C,Oct 29, 2025
- Review from Viator
5.00I booked the sunset schooner cruise for 10/26/25 and it was wonderful! The sunset was gorgeous, the wind was perfect, the skipper looked the part, and the crew was very well trained. One of the absolute highlights of our 12 day Canada-New England cruise and the perfect way to spend the last evening before getting into Boston to fly home. A must do if you want to make a beautiful memory.
Best Sailing experience EVER!!!!!
bethbI9226TJ,Oct 26, 2025
- Review from Tripadvisor
5.00So fun! Great crew super relaxing. A great atmosphere. We had so much fun it went by so fast. We wanted to say longer. Great price especially with how beautiful and picturesque everything was.
Experience a true sailing ship!
DewSherr,Oct 25, 2025
- Review from Tripadvisor
4.00Really enjoyable and awesome view of the sunset. Was able to help lift the main sail and you're welcome to ask the crew questions. No actual seats are available, you sit on the top deck and have a direct view of the water. You can bring your own drinks and snacks but if it’s a windy day that will be quite the challenge as the ship leans heavily and the waves rock the boat pretty significantly. If you have motion sickness this is not for you. Loved the experience of being on a true 100 plus year old actual sail boat.
Outstanding experience
Kyle W,Oct 22, 2025
- Review from Viator
5.00Amazing experience - the captain was great! Very knowledgeable and shared great stories. Highly recommend to see the Portland coastline.
Great sailing experiance
David S,Oct 20, 2025
- Review from Viator
5.00The crew was great. It was a very windy day, and the crew took the time to explain the sailing process and what to expect.
Beautiful evening on the water.
Blanca L,Oct 19, 2025
- Review from Viator
4.00A wonderful tour that would have been better if the weather and been more cooperative (gray, cloudy, and not much wind for actual sailing). That is the way it goes with a tour dependent on nature. Still, the crew were amazing and kept us entertained. They made us feel welcome in helping with hoisting sails. Can’t wait to try this tour, possibly in the spring.
Related Experiences
Operated by Portland Schooner Co.