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 | ||
---|---|---|---|---|
July 27–31, 2024 Saturday to Wednesday |
4 nights | Full-private charter | Ladona | Learn More |
July 27–August 1, 2024 Saturday to Thursday |
5 nights | Hiking and island exploration | American Eagle | Learn More |
July 28–August 2, 2024 Sunday to Friday |
5 nights | Explore the Maine Coast | Heritage | Learn More |
July 28–31, 2024 Sunday to Wednesday |
3 nights | Lighthouse cruise | Angelique | Learn More |
July 28–31, 2024 Sunday to Wednesday |
3 nights | Kids & Family cruise | J. & E. Riggin | Learn More |
July 28–August 2, 2024 Sunday to Friday |
5 nights | Five-night wine, cheese & chocolate | Stephen Taber | Learn More |
July 28–August 3, 2024 Sunday to Saturday |
6 nights | Tallship Sailing & Seamanship Course | Mary Day | Learn More |
July 28–August 3, 2024 Sunday to Saturday |
6 nights | Six night cruise | Lewis R. French | Learn More |
July 28–31, 2024 Sunday to Wednesday |
3 nights | Three-night adventure | Grace Bailey | Learn More |
August 1–5, 2024 Thursday to Monday |
4 nights | Yoga and wellness cruise | Angelique | Learn More |
August 1–5, 2024 Thursday to Monday |
4 nights | Weekend escape | Ladona | Learn More |
August 1–5, 2024 Thursday to Monday |
4 nights | Eggemoggin Reach Regatta | Grace Bailey | Learn More |
August 2–7, 2024 Friday to Wednesday |
5 nights | Live music cruise | J. & E. Riggin | Learn More |
August 2–5, 2024 Friday to Monday |
3 nights | Eggemoggin Reach Regatta | American Eagle | Learn More |
August 3–7, 2024 Saturday to Wednesday |
4 nights | Perseid Meteor Showers | Heritage | 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