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 | ||
---|---|---|---|---|
September 14–18, 2025 Sunday to Thursday |
4 nights | Sip & Sail: Craft cocktails | J. & E. Riggin | Learn More |
September 14–18, 2025 Sunday to Thursday |
4 nights | Just sail & relax | Mary Day | Learn More |
September 14–20, 2025 Sunday to Saturday |
6 nights | Wine, Dine and Cheese tasting | Stephen Taber | Learn More |
September 14–17, 2025 Sunday to Wednesday |
3 nights | Lobsters, sailing and music | Heritage | Learn More |
September 14–19, 2025 Sunday to Friday |
5 nights | Fall Eastbound (Booked for private charter) | American Eagle | Learn More |
September 14–18, 2025 Sunday to Thursday |
4 nights | Full - private charter | Ladona | Learn More |
September 18–21, 2025 Thursday to Sunday |
3 nights | Three-night cruise | Lewis R. French | Learn More |
September 19–22, 2025 Friday to Monday |
3 nights | Three Night Adventure Hosted by Marc Evan Jackson | Grace Bailey | Learn More |
September 19–23, 2025 Friday to Tuesday |
4 nights | Lighthouses & lobster cruise | J. & E. Riggin | Learn More |
September 19–22, 2025 Friday to Monday |
3 nights | Fall weekend getaway | Mary Day | Learn More |
September 19–23, 2025 Friday to Tuesday |
4 nights | Autumn on the Bay | Ladona | Learn More |
September 20–26, 2025 Saturday to Friday |
6 nights | Explore the Maine Coast | Heritage | Learn More |
September 21–27, 2025 Sunday to Saturday |
6 nights | Six-night cruise with naturalist on board | Angelique | Learn More |
September 21–25, 2025 Sunday to Thursday |
4 nights | Autumn on the Bay | Stephen Taber | Learn More |
September 21–25, 2025 Sunday to Thursday |
4 nights | Celtic Isles | American Eagle | 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