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 206 sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
July 8–11, 2026 Wednesday to Saturday |
3 nights | $1100 | Lobsters, sailing & music | Heritage | Learn More |
|
July 10–19, 2026 Friday to Sunday |
9 nights | $2822 | Sail Boston! | American Eagle | Learn More |
|
July 10–14, 2026 Friday to Tuesday |
4 nights | $1285 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
July 10–14, 2026 Friday to Tuesday |
4 nights | $1398 | Chocolate with Kate Shaffer | Stephen Taber | Learn More |
|
July 10–13, 2026 Friday to Monday |
3 nights | $1420 | Sip & sail: Craft Cocktails | J. & E. Riggin | Learn More |
|
July 12–16, 2026 Sunday to Thursday |
4 nights | $1705 | Four night adventure | Grace Bailey | Learn More |
|
July 12–18, 2026 Sunday to Saturday |
6 nights | $1700 | Explore the Maine Coast | Heritage | Learn More |
|
July 12–16, 2026 Sunday to Thursday |
4 nights | $1450 | No itinerary; just relax & sail | Mary Day | Learn More |
|
July 13–18, 2026 Monday to Saturday |
5 nights | $2828 | 5-night sail: new moon | Ladona | Learn More |
|
July 14–17, 2026 Tuesday to Friday |
3 nights | $1340 | Skygazing: New moon | J. & E. Riggin | Learn More |
|
July 15–18, 2026 Wednesday to Saturday |
3 nights | $1120 | Classic Windjamming adventure | Lewis R. French | Learn More |
|
July 15–19, 2026 Wednesday to Sunday |
4 nights | $1398 | 4-night getaway | Stephen Taber | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1530 | Long weekend adventure | Grace Bailey | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1360 | Weekend getaway | Mary Day | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1345 | Kids & Family cruise | J. & E. Riggin | Learn More |
|
July 19–23, 2026 Sunday to Thursday |
4 nights | $1400 | Grandparents and Grandkids | Angelique | Learn More |
|
July 19–25, 2026 Sunday to Saturday |
6 nights | $1700 | Explore the Maine Coast | Heritage | Learn More |
|
July 19–25, 2026 Sunday to Saturday |
6 nights | $1675 | How far can we get from Camden? | Lewis R. French | Learn More |
|
July 19–24, 2026 Sunday to Friday |
5 nights |
Inquire w/ Vessel |
Full- reserved for private charter | Ladona | Learn More |
|
July 20–25, 2026 Monday to Saturday |
5 nights | $1628 | Camden Classic Cup Regatta | 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
