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.
217 sailing adventures found.
| Dates | Length | Vessel | ||
|---|---|---|---|---|
| July 20–23, 2025 Sunday to Wednesday |
3 nights | Kids & Family cruise | J. & E. Riggin | Learn More |
| July 20–26, 2025 Sunday to Saturday |
6 nights | Six-night cruise | Lewis R. French | Learn More |
| July 20–26, 2025 Sunday to Saturday |
6 nights | Explore the Maine Coast | Heritage | Learn More |
| July 21–26, 2025 Monday to Saturday |
5 nights | Camden Classics Regatta | Angelique | Learn More |
| July 22–26, 2025 Tuesday to Saturday |
4 nights | Camden Classics Regatta | Grace Bailey | Learn More |
| July 22–26, 2025 Tuesday to Saturday |
4 nights | Just sail & relax | Mary Day | Learn More |
| July 22–26, 2025 Tuesday to Saturday |
4 nights | Full - private charter | Stephen Taber | Learn More |
| July 23–26, 2025 Wednesday to Saturday |
3 nights | Skygazing: new moon | J. & E. Riggin | Learn More |
| July 23–26, 2025 Wednesday to Saturday |
3 nights | Main Sails and Lobster Tails | American Eagle | Learn More |
| July 26–30, 2025 Saturday to Wednesday |
4 nights | Full - private charter | Ladona | Learn More |
| July 27–30, 2025 Sunday to Wednesday |
3 nights | Three Night Adventure | Grace Bailey | Learn More |
| July 27–August 2, 2025 Sunday to Saturday |
6 nights | Whales and seabirds cruise | Angelique | Learn More |
| July 27–August 2, 2025 Sunday to Saturday |
6 nights | Music & storytelling cruise | J. & E. Riggin | Learn More |
| July 27–August 2, 2025 Sunday to Saturday |
6 nights | Lighthouse cruise | Mary Day | Learn More |
| July 27–30, 2025 Sunday to Wednesday |
3 nights | Three-night cruise | Lewis R. French | 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
