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 | Price | ||
|---|---|---|---|---|
|
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 |
|
June 2–6, 2026 Tuesday to Saturday |
4 nights | $1240 | Four night adventure | Learn More |
|
June 7–13, 2026 Sunday to Saturday |
6 nights | $2265 | Windjammer Gam with live music | Learn More |
|
June 14–18, 2026 Sunday to Thursday |
4 nights | $1450 | Four night adventure | Learn More |
|
June 19–22, 2026 Friday to Monday |
3 nights | $1240 | Long weekend adventure | Learn More |
|
June 23–27, 2026 Tuesday to Saturday |
4 nights | $1450 | Four night adventure | Learn More |
|
June 28–July 4, 2026 Sunday to Saturday |
6 nights | $2265 | The Great Schooner Race | Learn More |
|
July 5–11, 2026 Sunday to Saturday |
6 nights | $2265 | Six night adventure | Learn More |
|
July 12–16, 2026 Sunday to Thursday |
4 nights | $1705 | Four night adventure | Learn More |
|
July 17–20, 2026 Friday to Monday |
3 nights | $1530 | Long weekend adventure | Learn More |
|
July 21–25, 2026 Tuesday to Saturday |
4 nights | $1705 | Camden Classics Regatta | Learn More |
|
July 26–29, 2026 Sunday to Wednesday |
3 nights | $1530 | Sailing & Maine humor with Gary Crocker | Learn More |
|
July 30–August 3, 2026 Thursday to Monday |
4 nights | $1705 | Eggemoggin Reach Regatta | Learn More |
|
August 4–8, 2026 Tuesday to Saturday |
4 nights | $1705 | Four night adventure | Learn More |
|
August 9–15, 2026 Sunday to Saturday |
6 nights | $2265 | Six night adventure | Learn More |
|
August 16–22, 2026 Sunday to Saturday |
6 nights | $2265 | Music & Sailing with Dennis Warner | Learn More |
|
August 23–27, 2026 Sunday to Thursday |
4 nights | $1705 | Four night adventure | Learn More |
|
August 28–31, 2026 Friday to Monday |
3 nights | $1530 | Long weekend adventure | Learn More |
|
September 1–5, 2026 Tuesday to Saturday |
4 nights | $1705 | Camden Windjammer Festival | Learn More |
|
September 6–12, 2026 Sunday to Saturday |
6 nights | $2105 | Music & Sailing with Mike & Amy Aiken | Learn More |
|
September 13–19, 2026 Sunday to Saturday |
6 nights | $2105 | WoodenBoat Rendez-Vous | Learn More |
|
September 20–24, 2026 Sunday to Thursday |
4 nights | $1550 | Four night adventure | Learn More |
|
September 25–28, 2026 Friday to Monday |
3 nights | $1375 | Long weekend adventure | Learn More |
|
September 29–October 3, 2026 Tuesday to Saturday |
4 nights | $1450 | Fall Foilage 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.
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