Overview
Available languages
2 hours
Mobile ticket
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is 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. See Fort Gorges, Bug Light Park, and the beautiful Portland coastline. 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
Not recommended for travelers with poor cardiovascular health
Public transportation options are available nearby
Infants and small children can ride in a pram or stroller
Suitable for all physical fitness levels
What To Expect
Casco Bay
See the beautiful inlet of Casco Bay in the Gulf of Maine. Staying within the bay, you will experience the calm, cool waters as the wind takes us along.
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
Casco Bay Morning Windjammer Sail
What‘s Included
Life jackets for adults and children
2 Hour Cruise
Environmentally friendly marine composting toilet
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
22 reviews
Total reviews and rating from Viator & Tripadvisor
Relaxing cruise
albertolG141TG,Jun 15, 2026
- Review from Tripadvisor
4.00The cruise was very relaxing. Crew members were nice. I would rate this as 5/5 if it was narrated. Although you can ask questions, but most of the young crew were busy with the sails. So for two hours you end up seating and wondering what you are seeing. Parking is outrageous. If you are not careful where you park as they are all marked public parking.. you can end up paying 9$ or more an hr. There’s one place (Simba) very close to the pier that’s charge 20$ the whole day which is a better deal.
Beautiful start to the day.
Frank C,May 17, 2026
- Review from Viator
5.00Relaxing tour of the bay. Fresh air & sun! Don’t forget a hat and sunscreen. Staff are friendly and extremely helpful.
Great Customer Service
Serena C,Mar 2, 2026
- Review from Viator
5.00I wasn’t able to make it however they were kind enough to call me and offer a different time slot which was highly appreciated
Try this cruise-you won't be disappointed
Steven C,Sep 20, 2025
- Review from Viator
5.00We got to sail on a 101 year old schooner. The weather was great but we did not have enough wind to fill the sails. The sails were raised and anyone who was willing was able to join in. It was lovely to see the huge sails ready to push us along . Even if we could not have the wind take across the water-the crew was great. Heill was a great tour guide and so interesting. She answered all our questions and listened to our stories. We felt very safe having her and Jake crew the boat. Our captain was very friendly and made us know we were safe.
Excellent vibes
Samuel H,Sep 2, 2025
- Review from Tripadvisor
5.00Friendly crew, great ride around the harbor on a beautiful working sailboat, and all around great vibes. This booking is def more of a ride than a tour— the crew do not have a pre-planned narrative describing the highlights of the bay— but the crew will answer any questions you have and were very friendly.
Fun way to get out on the...
Steve W,Aug 27, 2025
- Review from Viator
5.00Fun way to get out on the water. Leisurely cruise. It isn’t narrated but the crew is happy to answer questions.
Had such a great time on...
Haley S,Aug 13, 2025
- Review from Viator
5.00Had such a great time on the Casco Bay Morning Windjammer sail! The breeze was perfect, the views were beautiful, and the crew was super chill and friendly. It’s a really relaxing way to spend the morning in Portland. Oh, and definitely bring your own drinks and snacks if you want — makes it even better. Totally 5 stars from me!
Awesome time with Jacob and Erica!
Gisela D,Aug 10, 2025
- Review from Tripadvisor
5.00Thanks to Karen, Jacob and Erica for a wonderful time this morning. We had the luck to have a private sail where they complied to our petitions! They were easy going and very professional! We strongly recommend it!
Great views!
R5081TWaustind,Aug 3, 2025
- Review from Tripadvisor
5.00Went for a bachelor party and had a great time. Beautiful views of the bay and friendly/knowledgeable crew! Would go again!
I got engaged on the...
Stephen D,Aug 2, 2025
- Review from Viator
5.00I got engaged on the timberwind, and the captain and crew were excellent. A great experience and wonderful memory.
Related Experiences
Operated by Portland Schooner Co.