Find My Trip
Use the “Find My Trip” tool to search for cruises by date. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page. Clicking “Learn more” will bring you to each Windjammer’s individual website where you can find cabin availability and all the details.
Prices start at $875 per person. Your cruise fare covers the entire experience: the sailing, all home-cooked meals, hors d’oeuvres, and desserts, and your private cabin aboard a historical schooner. Shore excursions—including the beloved island lobster bake—are included, with no hidden fees or extra charges along the way.
We found 110 total 4 night and 5 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
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 6–11, 2026 Sunday to Friday |
5 nights | $1500 | Explore the Maine Coast | Heritage | Learn More |
|
September 7–12, 2026 Monday to Saturday |
5 nights | $1495 | Knit-a-long w/The Cashmere Goat | 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 13–18, 2026 Sunday to Friday |
5 nights | $1495 | WoodenBoat Rendezvous | Lewis R. French | 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 20–24, 2026 Sunday to Thursday |
4 nights | $1184 | Celtic Isles | American Eagle | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1550 | Four night adventure | Grace Bailey | 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 | $1450 | 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 | $1120 | Lighthouses! | Lewis R. French | Learn More |
|
September 25–29, 2026 Friday to Tuesday |
4 nights | $1998 | Autumn on the Bay | Ladona | Learn More |
|
September 25–29, 2026 Friday to Tuesday |
4 nights | $1445 | Sip & Sail: Craft beers of Maine | J. & E. Riggin | Learn More |
|
September 26–30, 2026 Saturday to Wednesday |
4 nights | $1300 | Fall Foliage | Heritage | Learn More |
|
September 27–October 1, 2026 Sunday to Thursday |
4 nights | $1228 | Autumn on the Bay | Stephen Taber | 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
