Find My Trip
Use the “Find My Trip” tool to search for cruises by date. Windjammers begin sailing in late May and end in mid-October. You can also find each vessel’s schedule by visiting their fleet page. Clicking “Learn more” will bring you to each Windjammer’s individual website where you can find cabin availability and all the details.
Prices start at $875 per person. Your cruise fare covers the entire experience: the sailing, all home-cooked meals, hors d’oeuvres, and desserts, and your private cabin aboard a historical schooner. Shore excursions—including the beloved island lobster bake—are included, with no hidden fees or extra charges along the way.
Maine resident? Learn more about our Maine resident discounts!
Hoping to sail in August? Visit our featured August sailings.
We found 238 sailing adventures.
| Dates | Length | Price /person |
Vessel | ||
|---|---|---|---|---|---|
|
July 21–26, 2027 Wednesday to Monday |
5 nights |
Inquire w/ Vessel |
FULL - private charter | Stephen Taber | Learn More |
|
July 23–26, 2027 Friday to Monday |
3 nights | $1530 | Long Weekend Adventure | Grace Bailey | Learn More |
|
July 24–25, 2027 Saturday to Sunday |
1 nights |
Inquire w/ Vessel |
Available for private charter | J. & E. Riggin | Learn More |
|
July 25–31, 2027 Sunday to Saturday |
6 nights | $1850 | Whales & Seabirds cruise | Angelique | Learn More |
|
July 25–31, 2027 Sunday to Saturday |
6 nights | $1800 | How far can we get from Camden? | Lewis R. French | Learn More |
|
July 25–30, 2027 Sunday to Friday |
5 nights | $1725 | Lighthouses & Shore Trips | Heritage | Learn More |
|
July 25–31, 2027 Sunday to Saturday |
6 nights | $1920 | Music & Storytelling w/Geoff Kauffman | J. & E. Riggin | Learn More |
|
July 26–29, 2027 Monday to Thursday |
3 nights | $1440 | Early-Week Escape | American Eagle | Learn More |
|
July 27–August 1, 2027 Tuesday to Sunday |
5 nights | $1708 | 5-night getaway | Stephen Taber | Learn More |
|
July 27–31, 2027 Tuesday to Saturday |
4 nights | $1705 | Camden Classics Regatta | Grace Bailey | Learn More |
|
July 30–August 3, 2027 Friday to Tuesday |
4 nights | $1686 | Islands & Villages | American Eagle | Learn More |
|
August 1–5, 2027 Sunday to Thursday |
4 nights | $1550 | Grandparents and Grandkids | Angelique | Learn More |
|
August 1–7, 2027 Sunday to Saturday |
6 nights | $1800 | Swan's Island Music Festival | Lewis R. French | Learn More |
|
August 1–5, 2027 Sunday to Thursday |
4 nights | $1725 | Perseid Meteor Showers | Heritage | Learn More |
|
August 1–5, 2027 Sunday to Thursday |
4 nights | $1645 | Sip & Sail: Wine pairing w/Kim Hamlin | J. & E. Riggin | Learn More |
|
August 1–7, 2027 Sunday to Saturday |
6 nights | $2265 | Swan's Island Music Festival | Grace Bailey | Learn More |
|
August 3–7, 2027 Tuesday to Saturday |
4 nights |
Inquire w/ Vessel |
FULL - private charter | Stephen Taber | Learn More |
|
August 4–8, 2027 Wednesday to Sunday |
4 nights | $1686 | Bays & Islands | American Eagle | Learn More |
|
August 5–9, 2027 Thursday to Monday |
4 nights | $1570 | Maine Lighthouses & Lobsters™ | J. & E. Riggin | Learn More |
|
August 6–9, 2027 Friday to Monday |
3 nights | $1350 | Weekend getaway | Angelique | 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
