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 10–15, 2026 Monday to Saturday |
5 nights | $1533 | Meteors & Music w/Darlin' Corey | American Eagle | Learn More |
|
August 10–14, 2026 Monday to Friday |
4 nights | $1300 | Lobsters, sailing & music | Heritage | Learn More |
|
August 11–15, 2026 Tuesday to Saturday |
4 nights | $1480 | Perseids Meteor showers | J. & E. Riggin | Learn More |
|
August 14–18, 2026 Friday to Tuesday |
4 nights | $1350 | Windjammer & Watercolors | Angelique | Learn More |
|
August 15–19, 2026 Saturday to Wednesday |
4 nights | $1300 | Sail the Maine Coast w/Murder Mystery dinner! | Heritage | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1466 | Hiking & Island exploration | American Eagle | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1468 | Music w/ Cara & Friends | Stephen Taber | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1450 | No itinerary; just relax & sail | Mary Day | Learn More |
|
August 16–20, 2026 Sunday to Thursday |
4 nights | $1460 | Maine Lighthouses & Lobsters | J. & E. Riggin | Learn More |
|
August 17–21, 2026 Monday to Friday |
4 nights | $1365 | Sailing & Kayaking | Lewis R. French | Learn More |
|
August 17–21, 2026 Monday to Friday |
4 nights | $2388 | 4-night sail | Ladona | Learn More |
|
August 19–23, 2026 Wednesday to Sunday |
4 nights | $1350 | 4-night cruise: FULL | Angelique | Learn More |
|
August 20–24, 2026 Thursday to Monday |
4 nights | $1300 | Lobsters, sailing & music | Heritage | Learn More |
|
August 23–27, 2026 Sunday to Thursday |
4 nights | $1705 | Four night adventure | Grace Bailey | Learn More |
|
August 24–29, 2026 Monday to Saturday |
5 nights | $1620 | Maine knitting cruise w/Bristol Ivy | J. & E. Riggin | Learn More |
|
August 25–29, 2026 Tuesday to Saturday |
4 nights | $1466 | Bays & islands | American Eagle | Learn More |
|
August 25–29, 2026 Tuesday to Saturday |
4 nights | $1450 | includes Farm-to-Table Barn dinner | Angelique | Learn More |
|
August 25–30, 2026 Tuesday to Sunday |
5 nights | $1500 | Explore the Maine Coast | Heritage | Learn More |
|
August 25–29, 2026 Tuesday to Saturday |
4 nights | $1728 | Photo Expedition with Kike Calvo | Stephen Taber | Learn More |
|
August 25–29, 2026 Tuesday to Saturday |
4 nights | $1450 | No itinerary; just relax & sail | Mary Day | 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
