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 | ||
|---|---|---|---|
| October 1–4, 2023 Sunday to Wednesday |
3 nights | Fall Foliage |
Learn More Open in New Tab |
| October 5–9, 2023 Thursday to Monday |
4 nights | Fall Foliage |
Learn More Open in New Tab |
| June 4–8, 2024 Tuesday to Saturday |
4 nights | Four-night adventure |
Learn More Open in New Tab |
| June 9–14, 2024 Sunday to Friday |
5 nights | Windjammer Gam |
Learn More Open in New Tab |
| June 16–22, 2024 Sunday to Saturday |
6 nights | Sailing & music |
Learn More Open in New Tab |
| June 23–29, 2024 Sunday to Saturday |
6 nights | Western Wanderer |
Learn More Open in New Tab |
| June 30–July 6, 2024 Sunday to Saturday |
6 nights | Great Schooner Race |
Learn More Open in New Tab |
| July 7–11, 2024 Sunday to Thursday |
4 nights | Four-night adventure hosted by Marc Evan Jackson |
Learn More Open in New Tab |
| July 12–16, 2024 Friday to Tuesday |
4 nights | Four-night adventure hosted by Marc Evan Jackson |
Learn More Open in New Tab |
| July 17–22, 2024 Wednesday to Monday |
5 nights | Five-night adventure |
Learn More Open in New Tab |
| July 23–27, 2024 Tuesday to Saturday |
4 nights | Camden Classics Regatta |
Learn More Open in New Tab |
| July 28–31, 2024 Sunday to Wednesday |
3 nights | Three-night adventure |
Learn More Open in New Tab |
| August 1–5, 2024 Thursday to Monday |
4 nights | Eggemoggin Reach Regatta |
Learn More Open in New Tab |
| August 6–9, 2024 Tuesday to Friday |
3 nights | Three-night adventure |
Learn More Open in New Tab |
| August 10–17, 2024 Saturday to Saturday |
7 nights | The Great Seven-Night Adventure |
Learn More Open in New Tab |
| August 23–26, 2024 Friday to Monday |
3 nights | Three-night adventure |
Learn More Open in New Tab |
| August 27–31, 2024 Tuesday to Saturday |
4 nights | Camden Windjammer Festival hosted by Marc Evan Jackson |
Learn More Open in New Tab |
| September 1–7, 2024 Sunday to Saturday |
6 nights | Sailing & music |
Learn More Open in New Tab |
| September 15–19, 2024 Sunday to Thursday |
4 nights | Four-night adventure hosted by Marc Evan Jackson |
Learn More Open in New Tab |
| September 20–23, 2024 Friday to Monday |
3 nights | Three-night adventure hosted by Marc Evan Jackson |
Learn More Open in New Tab |
| September 24–28, 2024 Tuesday to Saturday |
4 nights | Four-night adventure |
Learn More Open in New Tab |
| September 29–October 3, 2024 Sunday to Thursday |
4 nights | Fall Foliage Four-night adventure |
Learn More Open in New Tab |
| October 4–8, 2024 Friday to Tuesday |
4 nights | Fall Foliage Four-night adventure |
Learn More Open in New Tab |
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
