Find My Trip
Use the “Book My Trip” box above to search for cruise dates. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page.
136 sailing adventures found.
Dates | Length | Vessel | ||
---|---|---|---|---|
September 22–26, 2024 Sunday to Thursday |
4 nights | Autumn on the Bay | Stephen Taber | Learn More |
September 24–28, 2024 Tuesday to Saturday |
4 nights | Fall foliage! | Mary Day | Learn More |
September 24–28, 2024 Tuesday to Saturday |
4 nights | Lighthouse cruise | Lewis R. French | Learn More |
September 24–28, 2024 Tuesday to Saturday |
4 nights | Four-night adventure | Grace Bailey | Learn More |
September 25–29, 2024 Wednesday to Sunday |
4 nights | Scenic Maine Photography cruise | J. & E. Riggin | Learn More |
September 25–29, 2024 Wednesday to Sunday |
4 nights | Four-night cruise | Ladona | Learn More |
September 25–29, 2024 Wednesday to Sunday |
4 nights | That's it for 2024! | American Eagle | Learn More |
September 27–October 1, 2024 Friday to Tuesday |
4 nights | Autumn on the Bay | Stephen Taber | Learn More |
September 28–October 1, 2024 Saturday to Tuesday |
3 nights | Lobsters, sailing and music | Heritage | Learn More |
September 29–October 3, 2024 Sunday to Thursday |
4 nights | Lighthouse and foliage cruise | Angelique | Learn More |
September 29–October 5, 2024 Sunday to Saturday |
6 nights | Six-night cruise | Lewis R. French | Learn More |
September 29–October 3, 2024 Sunday to Thursday |
4 nights | Fall Foliage Four-night adventure | Grace Bailey | Learn More |
September 30–October 4, 2024 Monday to Friday |
4 nights | Maine Lighthouses and Lobsters | J. & E. Riggin | Learn More |
September 30–October 4, 2024 Monday to Friday |
4 nights | Fall colors cruise | Ladona | Learn More |
October 3–7, 2024 Thursday to Monday |
4 nights | Fall Colors | Stephen Taber | Learn More |
Trying to book last minute?
You can find cabin availability on each vessel’s website. OR use this form to let us know when you’re hoping to sail, how many people are in your party and what length trip you’re looking for. This form goes to all our member vessels at once. Any of the windjammers that can accommodate you,will get back to you with cabin availability asap!
Stay in the Know
With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!
Monthly Newsletter SignupBrochures
You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.
Request a Packet Visit the Fleet Page