Find My Trip
Use the “Book My Trip” box above to search for cruise dates. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page.
136 sailing adventures found.
Dates | Length | Vessel | ||
---|---|---|---|---|
August 4–10, 2024 Sunday to Saturday |
6 nights | Captain's Choice | Stephen Taber | Learn More |
August 4–10, 2024 Sunday to Saturday |
6 nights | Swan's Island Music Festival | Lewis R. French | Learn More |
August 5–10, 2024 Monday to Saturday |
5 nights | Captain's favorite harbors cruise | Mary Day | Learn More |
August 5–9, 2024 Monday to Friday |
4 nights | Full-private charter | Ladona | Learn More |
August 6–10, 2024 Tuesday to Saturday |
4 nights | Watercolors cruise | Angelique | Learn More |
August 6–9, 2024 Tuesday to Friday |
3 nights | Three-night adventure | Grace Bailey | Learn More |
August 6–10, 2024 Tuesday to Saturday |
4 nights | Swan's Island Music Festival | American Eagle | Learn More |
August 8–11, 2024 Thursday to Sunday |
3 nights | Perseid Meteor Showers | Heritage | Learn More |
August 8–12, 2024 Thursday to Monday |
4 nights | Perseids Meteor Shower | J. & E. Riggin | Learn More |
August 10–14, 2024 Saturday to Wednesday |
4 nights | Full-private charter | Ladona | Learn More |
August 10–17, 2024 Saturday to Saturday |
7 nights | The Great Seven-Night Adventure | Grace Bailey | Learn More |
August 11–16, 2024 Sunday to Friday |
5 nights | Perseids meteor shower | Angelique | Learn More |
August 11–17, 2024 Sunday to Saturday |
6 nights | Off the grid: Pen Bay's Hidden Gems | Stephen Taber | Learn More |
August 11–17, 2024 Sunday to Saturday |
6 nights | Perseid Meteor Showers | Mary Day | Learn More |
August 11–15, 2024 Sunday to Thursday |
4 nights | Four-night cruise | 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