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 50 total 1 night, 2 night and 3 night sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
September 9–12, 2026 Wednesday to Saturday |
3 nights | $1048 | Coastal Classics | American Eagle | Learn More |
|
September 19–22, 2026 Saturday to Tuesday |
3 nights | $1080 | Classic Windjamming adventure | 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 25–28, 2026 Friday to Monday |
3 nights | $1360 | Weekend getaway | Mary Day | Learn More |
|
October 5–8, 2026 Monday to Thursday |
3 nights | $1048 | One Last Turn around the Bay | American Eagle | Learn More |
|
October 10–13, 2026 Saturday to Tuesday |
3 nights | $1478 | Fall colors | Ladona | Learn More |
|
May 28–31, 2027 Friday to Monday |
3 nights |
Inquire w/ Vessel |
Booked for private charter | Angelique | Learn More |
|
May 28–31, 2027 Friday to Monday |
3 nights | $930 | Memorial Day weekend | Lewis R. French | Learn More |
|
June 1–4, 2027 Tuesday to Friday |
3 nights | $1220 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
June 2–5, 2027 Wednesday to Saturday |
3 nights | $950 | Wildlife cruise | Angelique | Learn More |
|
June 2–5, 2027 Wednesday to Saturday |
3 nights | $1325 | Lobsters, Sailing & Music | Heritage | Learn More |
|
June 18–21, 2027 Friday to Monday |
3 nights | $1223 | Weekend Escape | American Eagle | Learn More |
|
June 18–21, 2027 Friday to Monday |
3 nights | $1135 | Classic Windjamming Adventure | Lewis R. French | Learn More |
|
June 18–21, 2027 Friday to Monday |
3 nights | $1360 | Father's Day Weekend Getaway | Mary Day | Learn More |
|
June 20–23, 2027 Sunday to Wednesday |
3 nights | $1200 | Father's Day Adventure | Angelique | Learn More |
|
June 23–26, 2027 Wednesday to Saturday |
3 nights | $1200 | Lighthouse cruise | Angelique | Learn More |
|
June 25–28, 2027 Friday to Monday |
3 nights |
Inquire w/ Vessel |
Three-night sail | J. & E. Riggin | Learn More |
|
June 25–28, 2027 Friday to Monday |
3 nights | $1240 | Long Weekend Adventure | Grace Bailey | Learn More |
|
June 27–30, 2027 Sunday to Wednesday |
3 nights | $1135 | Photography with Justin | 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
