Casco Bay Windjammer Sail: Historic Schooner Cruise

Experience a two-hour Windjammer Sail on Casco Bay, Portland, Maine. Enjoy lighthouses, seals, and seabirds. Perfect for all ages. Bring your favorite wine or beer.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Casco Bay - Experience the stunning rugged coastline, adorned with lighthouses and seals, as the journey glides through the clear waters of Casco Bay.
  • Portland - Admire the beautiful skyline of Portland, Maine’s largest city, founded in 1786. Witness Portland’s bustling waterfront as fishing boats set sail and return to the wharves, which are…
What's Included
  • Environmentally friendly marine composting toilet
  • Life jackets for adults and children
  • 2 Hour Cruise
What's Not Included
  • 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!
Additional Information

Join us for a delightful two-hour Windjammer Sail on Casco Bay in Portland, Maine, an ideal way to admire the stunning rugged coastline, featuring lighthouses, seals, and seabirds.
(Note: This is not a narrated tour, but our crew is more than happy to answer any questions you may have about the sights).
People of all ages are welcome, whether you’re nine…

Location
56 Commercial St
Commercial Street
Please check your reservation to see the meeting point for your cruise. We are at the end of the Maine State Pier. Walk past Gate 5 of the Casco Bay Ferry to the dock house on the right-hand side to receive your tickets.
Cancellation Policy

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

Customer Ratings
4.8
(144 Ratings)
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Cecily_c
Oct 29, 2025
A must do for beautiful memories - I 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.
Review provided by Viator
Bethbi9226tj
Oct 26, 2025
Best Sailing experience EVER!!!!! - So 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.
Review provided by Tripadvisor
Kyle_w
Oct 22, 2025
Outstanding experience - Amazing experience - the captain was great! Very knowledgeable and shared great stories. Highly recommend to see the Portland coastline.
Review provided by Viator
David_s
Oct 20, 2025
Great sailing experiance - The crew was great. It was a very windy day, and the crew took the time to explain the sailing process and what to expect.
Review provided by Viator
Cody_c
Oct 16, 2025
Fun sunset cruise - Awesome experience. My girlfriend and I had a wonderful time. A little chilly but we prepared for it and stayed warm. The crew was great and full of good information on the sights. I would definitely recommend this trip to anyone in the area.
Review provided by Viator
Brian_m
Oct 16, 2025
I hadn't been Sailing in... - I hadn't been Sailing in a long while so going out on the ship was a real treat. Its really well maintained and perfect to take in the sights of Portlands harbor. The crew are all super nice and happy to share what they know about the boats history. 110% recommend it if your thinking about wanting to go on a ship like that
Review provided by Viator
Jasonbi3745uk
Nov 1, 2025
Great boat, fun trip - Great 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.
Review provided by Tripadvisor
Dewsherr
Oct 25, 2025
Experience a true sailing ship! - Really 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.
Review provided by Tripadvisor
Blanca_l
Oct 19, 2025
Beautiful evening on the water. - A 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.
Review provided by Viator
Ray_s
Nov 1, 2025
Great scenery, but very cold and uncomfortable. - It was EXTREMELY COLD! I wish there had been seats. The seating situation wasn't comfortable at all. The scenery was nice.
Review provided by Viator
From $77
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).