GRACE BAILEY has the space to relax and the size to offer smooth sailing. This makes her a fun and comfortable sailboat for couples, families, and charter groups.
Aboard our schooner is THE way to explore the best of Maine’s rugged beauty. This bold, new perspective makes our trips different. These trips stand out. You will remember them for the rest of your life. We guarantee it.
- Captain Sam Sikkema and Suzannah Smith
Max. Guests
29
Length on Deck
80’
Length Overall
118’
Homeport
Rockland, Maine
Built-In
1882, Patchogue, New York
Grace Bailey Reservations:
(207) 691-9521
| Dates | Length | ||
|---|---|---|---|
| June 8–13, 2025 Sunday to Friday |
5 nights | Windjammer Gam | Learn More |
| June 15–21, 2025 Sunday to Saturday |
6 nights | Music + Sailing Six Night Adventure | Learn More |
| June 22–28, 2025 Sunday to Saturday |
6 nights | Western Wanderer | Learn More |
| June 29–July 5, 2025 Sunday to Saturday |
6 nights | The Great Schooner Race | Learn More |
| July 6–10, 2025 Sunday to Thursday |
4 nights | Four Night Adventure | Learn More |
| July 11–15, 2025 Friday to Tuesday |
4 nights | Four Night Adventure | Learn More |
| July 16–21, 2025 Wednesday to Monday |
5 nights | Five Night Adventure | Learn More |
| July 22–26, 2025 Tuesday to Saturday |
4 nights | Camden Classics Regatta | Learn More |
| July 27–30, 2025 Sunday to Wednesday |
3 nights | Three Night Adventure | Learn More |
| July 31–August 4, 2025 Thursday to Monday |
4 nights | Eggemoggin Reach Regatta | Learn More |
| August 5–9, 2025 Tuesday to Saturday |
4 nights | Four Night Adventure | Learn More |
| August 10–16, 2025 Sunday to Saturday |
6 nights | Six Night Adventure | Learn More |
| August 17–21, 2025 Sunday to Thursday |
4 nights | Four Night Adventure | Learn More |
| August 22–25, 2025 Friday to Monday |
3 nights | Three Night adventure | Learn More |
| August 26–30, 2025 Tuesday to Saturday |
4 nights | Camden Windjammer Festival | Learn More |
| August 31–September 6, 2025 Sunday to Saturday |
6 nights | Music + Sailing Six Night Adventure | Learn More |
| September 7–13, 2025 Sunday to Saturday |
6 nights | WoodenBoat Rendez-Vous | Learn More |
| September 14–18, 2025 Sunday to Thursday |
4 nights | Four Night Adventure | Learn More |
| September 19–22, 2025 Friday to Monday |
3 nights | Three Night Adventure | Learn More |
| September 23–27, 2025 Tuesday to Saturday |
4 nights | Four Night Adventure | Learn More |
| September 28–October 2, 2025 Sunday to Thursday |
4 nights | Four Night Adventure | Learn More |
| October 3–6, 2025 Friday to Monday |
3 nights | Fall Foliage Three Night Adventure | Learn More |
| October 7–11, 2025 Tuesday to Saturday |
4 nights | Fall Foliage Four Night Adventure | Learn More |
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
