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 | ||
|---|---|---|---|---|---|
|
September 13–18, 2026 Sunday to Friday |
5 nights | $1420 | WoodenBoat Rendezvous | Lewis R. French | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $1678 | WoodenBoat Rendezvous | Stephen Taber | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $1550 | WoodenBoat Rendezvous | Mary Day | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $1590 | WoodenBoat Rendez-vous | J. & E. Riggin | Learn More |
|
September 14–19, 2026 Monday to Saturday |
5 nights | $2368 | WoodenBoat Rendezvous | Ladona | Learn More |
|
September 19–24, 2026 Saturday to Thursday |
5 nights | $1500 | Explore the Maine Coast | Heritage | Learn More |
|
September 19–22, 2026 Saturday to Tuesday |
3 nights | $995 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1184 | Celtic Isles | American Eagle | Learn More |
|
September 20–26, 2026 Sunday to Saturday |
6 nights | $1699 | Maritime historian and naturalist on board | Angelique | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1550 | Four night adventure | Grace Bailey | Learn More |
|
September 20–26, 2026 Sunday to Saturday |
6 nights | $1728 | Wine, Dine & Cheese | Stephen Taber | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1998 | Autumn on the Bay | Ladona | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1290 | No itinerary; just relax & sail | Mary Day | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1345 | Maine Lighthouse & Lobsters | J. & E. Riggin | Learn More |
|
September 23–27, 2026 Wednesday to Sunday |
4 nights | $1055 | Knit along with Captain Becky | Lewis R. French | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $1048 | Main sails & Lobster tails | American Eagle | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $1375 | Long weekend adventure | Grace Bailey | Learn More |
|
September 25–29, 2026 Friday to Tuesday |
4 nights | $1998 | Autumn on the Bay | Ladona | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $958 | Weekend getaway | Mary Day | Learn More |
|
September 25–29, 2026 Friday to Tuesday |
4 nights | $1445 | Sip & Sail: Craft beers of Maine | J. & E. Riggin | 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
