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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 PDF Schedule

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

Monthly Newsletter Signup

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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