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 | ||
|---|---|---|---|---|---|
|
June 27–July 2, 2027 Sunday to Friday |
5 nights | $1568 | Music w/The Acadian Aces | Stephen Taber | Learn More |
|
June 29–July 3, 2027 Tuesday to Saturday |
4 nights | $1470 | Sip & Sail: Craft beers of Maine | J. & E. Riggin | Learn More |
|
June 29–July 3, 2027 Tuesday to Saturday |
4 nights | $1450 | Four Night Adventure | Grace Bailey | Learn More |
|
July 1–5, 2027 Thursday to Monday |
4 nights | $1525 | July 4th celebration | Heritage | Learn More |
|
July 5–10, 2027 Monday to Saturday |
5 nights | $1590 | Great Schooner Race | Lewis R. French | Learn More |
|
July 6–10, 2027 Tuesday to Saturday |
4 nights | $1525 | Great Schooner Race fleet gathering | Heritage | Learn More |
|
July 11–15, 2027 Sunday to Thursday |
4 nights | $1591 | Bays & Islands | American Eagle | Learn More |
|
July 11–15, 2027 Sunday to Thursday |
4 nights | $1550 | Grandparents and Grandkids | Angelique | Learn More |
|
July 11–15, 2027 Sunday to Thursday |
4 nights | $1570 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
July 11–15, 2027 Sunday to Thursday |
4 nights | $1498 | Wine trip with Michael Green | Stephen Taber | Learn More |
|
July 15–19, 2027 Thursday to Monday |
4 nights | $1450 | Sailing & Kayaking | Lewis R. French | Learn More |
|
July 16–20, 2027 Friday to Tuesday |
4 nights | $1438 | Weekend Escape | Stephen Taber | Learn More |
|
July 18–22, 2027 Sunday to Thursday |
4 nights | $1705 | Four Night Adventure | Grace Bailey | Learn More |
|
July 20–25, 2027 Tuesday to Sunday |
5 nights | $1934 | Coastal Classics | American Eagle | Learn More |
|
July 20–24, 2027 Tuesday to Saturday |
4 nights | $1550 | Camden Classics | Angelique | Learn More |
|
July 20–24, 2027 Tuesday to Saturday |
4 nights | $1420 | Classic Windjamming Adventure | Lewis R. French | Learn More |
|
July 21–26, 2027 Wednesday to Monday |
5 nights |
Inquire w/ Vessel |
FULL - private charter | Stephen Taber | Learn More |
|
July 25–30, 2027 Sunday to Friday |
5 nights | $1725 | Lighthouses & Shore Trips | Heritage | Learn More |
|
July 27–August 1, 2027 Tuesday to Sunday |
5 nights | $1708 | 5-night getaway | Stephen Taber | Learn More |
|
July 27–31, 2027 Tuesday to Saturday |
4 nights | $1705 | Camden Classics Regatta | 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
