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 | ||
|---|---|---|---|---|
| October 3–6, 2025 Friday to Monday |
3 nights | Fall Foliage Three Night Adventure | Grace Bailey | Learn More |
| October 4–8, 2025 Saturday to Wednesday |
4 nights | Fall colors | Ladona | Learn More |
| October 5–11, 2025 Sunday to Saturday |
6 nights | Six-night cruise | Lewis R. French | Learn More |
| October 6–9, 2025 Monday to Thursday |
3 nights | Fall Colors | Stephen Taber | Learn More |
| October 7–11, 2025 Tuesday to Saturday |
4 nights | Fall Foliage Four Night Adventure | Grace Bailey | Learn More |
| October 9–12, 2025 Thursday to Sunday |
3 nights | Fall colors | Ladona | 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
