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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

View Schedule Grace Bailey Website

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

Download 2025 PDF Schedule

Download 2024 PDF Schedule

Dates Length
June 23–29, 2024
Sunday to Saturday
6 nights Western Wanderer
June 30–July 6, 2024
Sunday to Saturday
6 nights Great Schooner Race
July 7–11, 2024
Sunday to Thursday
4 nights Four-night adventure hosted by Marc Evan Jackson
July 12–16, 2024
Friday to Tuesday
4 nights Four-night adventure hosted by Marc Evan Jackson
July 17–22, 2024
Wednesday to Monday
5 nights Five-night adventure
July 23–27, 2024
Tuesday to Saturday
4 nights Camden Classics Regatta
July 28–31, 2024
Sunday to Wednesday
3 nights Three-night adventure
August 1–5, 2024
Thursday to Monday
4 nights Eggemoggin Reach Regatta
August 6–9, 2024
Tuesday to Friday
3 nights Three-night adventure
August 10–17, 2024
Saturday to Saturday
7 nights The Great Seven-Night Adventure
August 23–26, 2024
Friday to Monday
3 nights Three-night adventure
August 27–31, 2024
Tuesday to Saturday
4 nights Camden Windjammer Festival hosted by Marc Evan Jackson
September 1–7, 2024
Sunday to Saturday
6 nights Sailing & music
September 15–19, 2024
Sunday to Thursday
4 nights Four-night adventure hosted by Marc Evan Jackson
September 20–23, 2024
Friday to Monday
3 nights Three-night adventure hosted by Marc Evan Jackson
September 24–28, 2024
Tuesday to Saturday
4 nights Four-night adventure
September 29–October 3, 2024
Sunday to Thursday
4 nights Fall Foliage Four-night adventure
October 4–8, 2024
Friday to Tuesday
4 nights Fall Foliage Four-night adventure
June 3–7, 2025
Tuesday to Saturday
4 nights Four Night Adventure
June 8–13, 2025
Sunday to Friday
5 nights Windjammer Gam Hosted by Marc Evan Jackson
June 15–21, 2025
Sunday to Saturday
6 nights Music + Sailing Six Night Adventure
June 22–28, 2025
Sunday to Saturday
6 nights Western Wanderer
June 29–July 5, 2025
Sunday to Saturday
6 nights The Great Schooner Race
July 6–10, 2025
Sunday to Thursday
4 nights Four Night Adventure Hosted by Marc Evan Jackson
July 11–15, 2025
Friday to Tuesday
4 nights Four Night Adventure Hosted by Marc Evan Jackson
July 16–21, 2025
Wednesday to Monday
5 nights Five Night Adventure
July 22–26, 2025
Tuesday to Saturday
4 nights Camden Classics Regatta
July 27–30, 2025
Sunday to Wednesday
3 nights Three Night Adventure
July 31–August 4, 2025
Thursday to Monday
4 nights Eggemoggin Reach Regatta
August 5–9, 2025
Tuesday to Saturday
4 nights Four Night Adventure
August 10–16, 2025
Sunday to Saturday
6 nights Six Night Adventure
August 17–21, 2025
Sunday to Thursday
4 nights Four Night Adventure
August 22–25, 2025
Friday to Monday
3 nights Three Night adventure
August 26–30, 2025
Tuesday to Saturday
4 nights Camden Windjammer Festival hosted by Marc Evan Jackson
August 31–September 6, 2025
Sunday to Saturday
6 nights Music + Sailing Six Night Adventure
September 7–13, 2025
Sunday to Saturday
6 nights WoodenBoat Rendez-Vous
September 14–18, 2025
Sunday to Thursday
4 nights Four Night Adventure Hosted by Marc Evan Jackson
September 19–22, 2025
Friday to Monday
3 nights Three Night Adventure Hosted by Marc Evan Jackson
September 23–27, 2025
Tuesday to Saturday
4 nights Four Night Adventure
September 28–October 2, 2025
Sunday to Thursday
4 nights Four Night Adventure
October 3–6, 2025
Friday to Monday
3 nights Fall Foliage Three Night Adventure
October 7–11, 2025
Tuesday to Saturday
4 nights Fall Foliage Four Night Adventure
Please note: We do our best to keep trip schedules as up-to-date as possible, however schedules are subject to change. We also do not track cabin availability on the Maine Windjammer Association website. For cabin availability or to confirm a specific sail date, please contact the vessel directly.

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!

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Brochures

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

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