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.
216 sailing adventures found.
Dates | Length | Vessel | ||
---|---|---|---|---|
June 13–16, 2025 Friday to Monday |
3 nights | Father's Day Getaway | Mary Day | Learn More |
June 13–16, 2025 Friday to Monday |
3 nights | Father's Day weekend cruise | Lewis R. French | Learn More |
June 15–21, 2025 Sunday to Saturday |
6 nights | Music + Sailing Six Night Adventure | Grace Bailey | Learn More |
June 15–21, 2025 Sunday to Saturday |
6 nights | Nature and photography cruise | Angelique | Learn More |
June 15–19, 2025 Sunday to Thursday |
4 nights | Maine knitting getaway | J. & E. Riggin | Learn More |
June 15–19, 2025 Sunday to Thursday |
4 nights | Bays and Islands | American Eagle | Learn More |
June 16–21, 2025 Monday to Saturday |
5 nights | Lighthouses & Shore Trips | Heritage | Learn More |
June 17–21, 2025 Tuesday to Saturday |
4 nights | Just sail & relax | Mary Day | Learn More |
June 17–21, 2025 Tuesday to Saturday |
4 nights | Four-night cruise | Lewis R. French | Learn More |
June 17–21, 2025 Tuesday to Saturday |
4 nights | Summer solstice with live music | Stephen Taber | Learn More |
June 17–21, 2025 Tuesday to Saturday |
4 nights | Summer solstice and live music | Ladona | Learn More |
June 19–23, 2025 Thursday to Monday |
4 nights | Summer solstice getaway | J. & E. Riggin | Learn More |
June 20–24, 2025 Friday to Tuesday |
4 nights | Summer Solstice | American Eagle | Learn More |
June 22–28, 2025 Sunday to Saturday |
6 nights | Western Wanderer | Grace Bailey | Learn More |
June 22–28, 2025 Sunday to Saturday |
6 nights | Six-night cruise with naturalist on board | Angelique | 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