Find My Trip
Use the “Find 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.
We found 276 sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
August 27–31, 2025 Wednesday to Sunday |
4 nights | $1358 | Camden Windjammer Festival | Stephen Taber | Learn More |
|
August 31–September 6, 2025 Sunday to Saturday |
6 nights | $1950 | Music + Sailing Six Night Adventure | Grace Bailey | Learn More |
|
August 31–September 6, 2025 Sunday to Saturday |
6 nights | $1549 | Six-night Labor Day cruise | Angelique | Learn More |
|
August 31–September 6, 2025 Sunday to Saturday |
6 nights | $1465 | Maine knitting getaway | J. & E. Riggin | Learn More |
|
August 31–September 1, 2025 Sunday to Monday |
1 nights | $490 | One-night Staycation cruise | Mary Day | Learn More |
|
August 31–September 6, 2025 Sunday to Saturday |
6 nights | $1540 | Explore the Maine Coast | Heritage | Learn More |
|
September 1–5, 2025 Monday to Friday |
4 nights | $1328 | Music w/Chicky Stoltz & Ragged Co. | Stephen Taber | Learn More |
|
September 1–7, 2025 Monday to Sunday |
6 nights | $2798 | Six-nights; no set itinerary | Ladona | Learn More |
|
September 2–6, 2025 Tuesday to Saturday |
4 nights | $1185 | Knit-a-long with Captain Becky | Lewis R. French | Learn More |
|
September 3–6, 2025 Wednesday to Saturday |
3 nights | $958 | Just sail & relax | Mary Day | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights | $1950 | WoodenBoat Rendez-Vous | Grace Bailey | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights |
Inquire w/ Vessel |
FULL - private charter | Angelique | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights | $1460 | WoodenBoat Rendezvous | J. & E. Riggin | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights | $1550 | Wooden Boat Rendezvous | Mary Day | Learn More |
|
September 7–12, 2025 Sunday to Friday |
5 nights | $1370 | WoodenBoat Rendez-Vous | Lewis R. French | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights | $1638 | WoodenBoat Rendezvous | Stephen Taber | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights | $1540 | Wooden Boat Fleet Gathering | Heritage | Learn More |
|
September 7–13, 2025 Sunday to Saturday |
6 nights | $1578 | Woodenboat Sail-In | American Eagle | Learn More |
|
September 8–13, 2025 Monday to Saturday |
5 nights | $2318 | WoodenBoat fleet rendez-vous | Ladona | Learn More |
|
September 13–17, 2025 Saturday to Wednesday |
4 nights | $1185 | Four-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
