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.
Maine resident? Learn more about our Maine resident discounts!
Hoping to sail in August? Visit our featured August sailings.
We found 127 total 4 night and 5 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
August 24–29, 2027 Tuesday to Sunday |
5 nights | $1760 | Maine Knitting cruise w/Bristol Ivy | J. & E. Riggin | Learn More |
|
August 27–31, 2027 Friday to Tuesday |
4 nights | $1686 | Bays & islands | American Eagle | Learn More |
|
August 31–September 4, 2027 Tuesday to Saturday |
4 nights | $1590 | Camden Windjammer Festival | J. & E. Riggin | Learn More |
|
August 31–September 4, 2027 Tuesday to Saturday |
4 nights | $1398 | Camden Windjammer Festival | Stephen Taber | Learn More |
|
August 31–September 4, 2027 Tuesday to Saturday |
4 nights | $1705 | Camden Windjammer Festival | Grace Bailey | Learn More |
|
September 5–10, 2027 Sunday to Friday |
5 nights | $1725 | Lighthouses & Shore Trips | Heritage | Learn More |
|
September 6–11, 2027 Monday to Saturday |
5 nights | $1590 | Knit along with Captain Becky | Lewis R. French | Learn More |
|
September 6–10, 2027 Monday to Friday |
4 nights | $1398 | Music w/Chicky Stoltz and Ragged Company | Stephen Taber | Learn More |
|
September 12–17, 2027 Sunday to Friday |
5 nights | $1590 | WoodenBoat Rendezvous | Lewis R. French | Learn More |
|
September 18–22, 2027 Saturday to Wednesday |
4 nights | $1525 | Lobsters, Sailing & Music | Heritage | Learn More |
|
September 19–23, 2027 Sunday to Thursday |
4 nights | $1475 | Bays & Islands | American Eagle | Learn More |
|
September 19–23, 2027 Sunday to Thursday |
4 nights |
Inquire w/ Vessel |
Four-night sail | J. & E. Riggin | Learn More |
|
September 19–23, 2027 Sunday to Thursday |
4 nights | $1550 | Four Night Adventure | Grace Bailey | Learn More |
|
September 22–26, 2027 Wednesday to Sunday |
4 nights | $1190 | Classic Windjamming Adventure | Lewis R. French | Learn More |
|
September 24–28, 2027 Friday to Tuesday |
4 nights | $1525 | Fall Foliage | Heritage | Learn More |
|
September 24–28, 2027 Friday to Tuesday |
4 nights | $1550 | Sip & Sail: Craft beers of Maine | J. & E. Riggin | Learn More |
|
September 26–30, 2027 Sunday to Thursday |
4 nights | $1278 | Autumn on the Bay | Stephen Taber | Learn More |
|
September 27–October 1, 2027 Monday to Friday |
4 nights | $1190 | Classic Windjamming Adventure | Lewis R. French | Learn More |
|
September 28–October 2, 2027 Tuesday to Saturday |
4 nights | $1364 | Autumn on the Bay | American Eagle | Learn More |
|
September 28–October 2, 2027 Tuesday to Saturday |
4 nights | $1450 | Fall Foliage Four Night Adventure | 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
