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.
217 sailing adventures found.
Dates | Length | Vessel | ||
---|---|---|---|---|
July 27–30, 2025 Sunday to Wednesday |
3 nights | Three-night cruise | Lewis R. French | Learn More |
July 27–30, 2025 Sunday to Wednesday |
3 nights | Three-night getaway | Stephen Taber | Learn More |
July 27–August 1, 2025 Sunday to Friday |
5 nights | Explore the Maine Coast | Heritage | Learn More |
July 27–August 2, 2025 Sunday to Saturday |
6 nights | Unscripted Adventure | American Eagle | Learn More |
July 30–August 2, 2025 Wednesday to Saturday |
3 nights | Three-night cruise | Lewis R. French | Learn More |
July 30–August 2, 2025 Wednesday to Saturday |
3 nights | Three-night getaway | Stephen Taber | Learn More |
July 31–August 4, 2025 Thursday to Monday |
4 nights | Eggemoggin Reach Regatta | Grace Bailey | Learn More |
July 31–August 7, 2025 Thursday to Thursday |
7 nights | Ports Unknown: Secrets of the Outer Islands | Ladona | Learn More |
August 2–6, 2025 Saturday to Wednesday |
4 nights | Perseid Meteor Showers | Heritage | Learn More |
August 3–7, 2025 Sunday to Thursday |
4 nights | Windjammers & Watercolors cruise | Angelique | Learn More |
August 3–8, 2025 Sunday to Friday |
5 nights | Music & dance cruise | J. & E. Riggin | Learn More |
August 3–9, 2025 Sunday to Saturday |
6 nights | Captain's favorite harbors cruise | Mary Day | Learn More |
August 3–9, 2025 Sunday to Saturday |
6 nights | Swan's Island Music Festival | Lewis R. French | Learn More |
August 3–9, 2025 Sunday to Saturday |
6 nights | Captain's Choice | Stephen Taber | Learn More |
August 3–7, 2025 Sunday to Thursday |
4 nights | Hiking and Island Exploration | American Eagle | 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