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 11–15, 2025 Friday to Tuesday |
4 nights | Four Night Adventure Hosted by Marc Evan Jackson | Grace Bailey | Learn More |
July 11–15, 2025 Friday to Tuesday |
4 nights | Grandparents & Grandkids cruise | Angelique | Learn More |
July 11–14, 2025 Friday to Monday |
3 nights | Sip & Sail: Craft cocktails | J. & E. Riggin | Learn More |
July 11–14, 2025 Friday to Monday |
3 nights | Three-night cruise | Lewis R. French | Learn More |
July 11–15, 2025 Friday to Tuesday |
4 nights | Weekend Escape | Stephen Taber | Learn More |
July 11–15, 2025 Friday to Tuesday |
4 nights | Hiking and Island Exploration | American Eagle | Learn More |
July 13–17, 2025 Sunday to Thursday |
4 nights | Just sail & relax | Mary Day | Learn More |
July 13–19, 2025 Sunday to Saturday |
6 nights | Explore the Maine Coast | Heritage | Learn More |
July 14–18, 2025 Monday to Friday |
4 nights | Four-nights, no set itinerary | Ladona | Learn More |
July 15–19, 2025 Tuesday to Saturday |
4 nights | Lighthouses & lobster cruise | J. & E. Riggin | Learn More |
July 15–19, 2025 Tuesday to Saturday |
4 nights | Four-night cruise | Lewis R. French | Learn More |
July 16–21, 2025 Wednesday to Monday |
5 nights | Five Night Adventure | Grace Bailey | Learn More |
July 16–20, 2025 Wednesday to Sunday |
4 nights | Lighthouse cruise | Angelique | Learn More |
July 16–20, 2025 Wednesday to Sunday |
4 nights | Four-night Getaway | Stephen Taber | Learn More |
July 17–22, 2025 Thursday to Tuesday |
5 nights | Eastbound: Blue Hill Bay and Beyond | 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