Skip to content or footer

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.

145 sailing adventures found.

Page 3 of 10
Dates Length Vessel
August 6–10, 2024
Tuesday to Saturday
4 nights Swan's Island Music Festival American Eagle
August 8–11, 2024
Thursday to Sunday
3 nights Perseid Meteor Showers Heritage
August 8–12, 2024
Thursday to Monday
4 nights Perseids Meteor Shower J. & E. Riggin
August 10–14, 2024
Saturday to Wednesday
4 nights Full-private charter Ladona
August 10–17, 2024
Saturday to Saturday
7 nights The Great Seven-Night Adventure Grace Bailey
August 11–16, 2024
Sunday to Friday
5 nights Perseids meteor shower Angelique
August 11–17, 2024
Sunday to Saturday
6 nights Off the grid: Pen Bay's Hidden Gems Stephen Taber
August 11–17, 2024
Sunday to Saturday
6 nights Perseid Meteor Showers Mary Day
August 11–15, 2024
Sunday to Thursday
4 nights Four-night cruise Lewis R. French
August 11–17, 2024
Sunday to Saturday
6 nights Unscripted Adventure American Eagle
August 13–18, 2024
Tuesday to Sunday
5 nights Explore the Maine Coast Heritage
August 13–18, 2024
Tuesday to Sunday
5 nights FULL- private charter J. & E. Riggin
August 15–22, 2024
Thursday to Thursday
7 nights Ports Unknown: Secrets of the Outer Islands Ladona
August 16–19, 2024
Friday to Monday
3 nights Three-night cruise Lewis R. French
August 17–20, 2024
Saturday to Tuesday
3 nights Lighthouse cruise Angelique
Page 3 of 10

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!

Please note: We do our best to keep trip schedules as up-to-date as possible, however schedules are subject to change. We also do not track cabin availability on the Maine Windjammer Association website. For cabin availability or to confirm a specific sail date, please contact the vessel directly.

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 Signup


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

You are using an outdated browser. Please upgrade your browser to improve your experience. We recommend Google Chrome.