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 30–31, 2026 Sunday to Monday |
1 nights |
Inquire w/ Vessel |
Available for private charter | Stephen Taber | Learn More |
|
August 30–September 5, 2026 Sunday to Saturday |
6 nights | $1550 | Camden Windjammer Festival | Mary Day | Learn More |
|
August 31–September 5, 2026 Monday to Saturday |
5 nights | $1500 | Camden Windjammer Festival - Fleet Gathering | Heritage | Learn More |
|
September 1–5, 2026 Tuesday to Saturday |
4 nights | $1705 | Camden Windjammer Festival | Grace Bailey | Learn More |
|
September 1–5, 2026 Tuesday to Saturday |
4 nights | $1358 | Camden Windjammer Festival | Stephen Taber | Learn More |
|
September 1–5, 2026 Tuesday to Saturday |
4 nights | $1480 | Camden Windjammer Festival | J. & E. Riggin | Learn More |
|
September 3–6, 2026 Thursday to Sunday |
3 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
|
September 6–12, 2026 Sunday to Saturday |
6 nights |
Inquire w/ Vessel |
Booked for private charter | Angelique | Learn More |
|
September 6–12, 2026 Sunday to Saturday |
6 nights | $2105 | Music & Sailing with Mike & Amy Aiken | Grace Bailey | Learn More |
|
September 6–11, 2026 Sunday to Friday |
5 nights | $1500 | Explore the Maine Coast | Heritage | Learn More |
|
September 6–12, 2026 Sunday to Saturday |
6 nights | $1550 | Lighthouse Cruise | Mary Day | Learn More |
|
September 6–12, 2026 Sunday to Saturday |
6 nights | $1660 | Maine Knitting retreat w/Margaret Radcliffe | J. & E. Riggin | Learn More |
|
September 7–12, 2026 Monday to Saturday |
5 nights | $1420 | Lighthouses! | Lewis R. French | Learn More |
|
September 7–11, 2026 Monday to Friday |
4 nights | $1358 | Music w/Chicky Stoltz and Ragged Company | Stephen Taber | Learn More |
|
September 7–13, 2026 Monday to Sunday |
6 nights | $2858 | 6-night sail | Ladona | Learn More |
|
September 9–12, 2026 Wednesday to Saturday |
3 nights | $1048 | Coastal Classics | American Eagle | Learn More |
|
September 12–18, 2026 Saturday to Friday |
6 nights | $1700 | WoodenBoat Rendez-vous - Fleet Gathering | Heritage | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $1657 | WoodenBoat RendezVous | American Eagle | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $1650 | WoodenBoat RendezVous | Angelique | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $2105 | WoodenBoat Rendez-Vous | Grace Bailey | 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
