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 10–14, 2023 Saturday to Wednesday |
4 nights | Learn More Open in New Tab |
|
| June 15–19, 2023 Thursday to Monday |
4 nights | Learn More Open in New Tab |
|
| June 20–24, 2023 Tuesday to Saturday |
4 nights | Featuring Tim Grimm | Learn More Open in New Tab |
| June 25–July 1, 2023 Sunday to Saturday |
6 nights | Western Wanderer | Learn More Open in New Tab |
| July 2–8, 2023 Sunday to Saturday |
6 nights | Great Schooner Race | Learn More Open in New Tab |
| July 9–15, 2023 Sunday to Saturday |
6 nights | Hosted by Marc Evan Jackson | Learn More Open in New Tab |
| July 16–20, 2023 Sunday to Thursday |
4 nights | Learn More Open in New Tab |
|
| July 21–25, 2023 Friday to Tuesday |
4 nights | Learn More Open in New Tab |
|
| July 31–August 3, 2023 Monday to Thursday |
3 nights | Learn More Open in New Tab |
|
| August 4–9, 2023 Friday to Wednesday |
5 nights | Eggemoggin Reach Regatta | Learn More Open in New Tab |
| August 10–14, 2023 Thursday to Monday |
4 nights | Learn More Open in New Tab |
|
| August 15–19, 2023 Tuesday to Saturday |
4 nights | Learn More Open in New Tab |
|
| August 20–24, 2023 Sunday to Thursday |
4 nights | Learn More Open in New Tab |
|
| August 25–28, 2023 Friday to Monday |
3 nights | Learn More Open in New Tab |
|
| August 29–September 2, 2023 Tuesday to Saturday |
4 nights | Camden Windjammer Festival | Learn More Open in New Tab |
| September 3–9, 2023 Sunday to Saturday |
6 nights | Featuring Mike and Amy Aiken | Learn More Open in New Tab |
| September 10–16, 2023 Sunday to Saturday |
6 nights | Wooden Boat Sail-In | Learn More Open in New Tab |
| September 22–25, 2023 Friday to Monday |
3 nights | Hosted by Marc Evan Jackson | Learn More Open in New Tab |
| September 26–30, 2023 Tuesday to Saturday |
4 nights | Learn More Open in New Tab |
|
| 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 |
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
