
Sail
Grace Bailey
2024 Adventures
Below is the schedule of our Maine sailing adventures for 2024, All trips depart from Rockland Maine.


Explore Secret Maine
Sept 1 - 7
Prices Starting at $1,790 pp
Music & Sailing with Mike & Amy Aiken.
6 Nights (Sun-Sat)
Sept 8 - 14
Prices Starting at $1,790 pp
WoodenBoat Sail-In Join us for the final Maine Windjammer Fleet gathering of the season at Wooden Boat Harbor in Brooklin, Maine. At the annual “Sail In" vessels from all over come to celebrate the history and beauty of their chosen passion - wooden boats! The WoodenBoat School, set in the beautiful Blue Hill region will host us, along with other traditional boats, for an afternoon of live music and celebration. Maine is celebrated for being the home of countless beautiful traditional wooden boats and rich and thriving Maritime culture. Come celebrate with us!
6 Nights (Sun-Sat)
Sept 15 - 19
Prices Starting at $1,395 pp
Four Night Adventure Hosted by Marc Evan Jackson Marc Evan Jackson is an actor known for his roles on Brooklyn Nine-Nine, The Good Place, Parks & Recreation, The Baby-Sitters Club, and many more. He is one of the owners of GRACE BAILEY. Thirty years ago, long before he was in Hollywood, Marc was the first mate of the GRACE BAILEY's former sister ship, the schooner MERCANTILE. Marc is thrilled to be keeping the tradition alive, and can't wait to share the magic of schooners, windjamming, and Maine with old salts and newcomers alike.
4 Nights (Sun-Thurs)
Sept 20 - 23
Prices Starting at $1,275 pp
Three Night Adventure Hosted by Marc Evan Jackson Marc Evan Jackson is an actor known for his roles on Brooklyn Nine-Nine, The Good Place, Parks & Recreation, The Baby-Sitters Club, and many more. He is one of the owners of GRACE BAILEY. Thirty years ago, long before he was in Hollywood, Marc was the first mate of the GRACE BAILEY's former sister ship, the schooner MERCANTILE. Marc is thrilled to be keeping the tradition alive, and can't wait to share the magic of schooners, windjamming, and Maine with old salts and newcomers alike.
3 Nights (Fri-Mon)
Sept 29 - Oct 3
Prices Starting at $1,295 pp
Fall Foliage Four Night Adventure Join us for one of our Fall Foliage adventures! With luck, the fall leaves will have turned and the coast will be electric with the warm fall yellows and oranges. Bring a cozy sweater for the crisp fall weather and sailing breeze.
4 Night (Tues-Sat)
Aug 1 - 5
Prices Starting at $1,480 pp
Eggemoggin Reach Regatta During this trip, we will sail to WoodenBoat Harbor in Brooklin, Maine to join the Eggemoggin Reach Regatta for the day of the race! The ERR, as its lovingly referred to, began humbly in 1985 with thirteen wooden boats. It was first envisioned as an opportunity for wooden boat owners to get to together and enjoy each others company as well as to compete. Now, it hosts more than a hundred vessels. Sailing along with the other classic yachts and racing boats, we will have the best seat in the house to watch the action!
4 Nights (Thurs-Mon)
Aug 6 - 9
Prices Starting at $1,310 pp
Three Night Adventure This three night adventure is the perfect taste of Windjamming during the heart of the summer! Join us for long sunny days of sailing and stunning sunsets at anchor as we sail around enjoying the beauty that the Penobscot Bay has to offer.
3 Nights (Tues-Fri)
Aug 10 - 17
Prices Starting at $2,150 pp
The Great Seven Night Adventure Please join us for our first ever seven night adventure! More days out at sea, mean more unexplored places to discover. On this trip, we will venture to the outer islands and explore places we wouldn't even dream of going on a shorter trip.
7 Nights (Sat-Sat)
Aug 27 - 31
Prices Starting at $1,540 pp
Camden Windjammer Festival Hosted by Marc Evan Jackson Marc Evan Jackson is an actor known for his roles on Brooklyn Nine-Nine, The Good Place, Parks & Recreation, The Baby-Sitters Club, and many more. He is one of the owners of GRACE BAILEY. Join us for four nights of island hopping and exploring, followed by the Camden Windjammer Festival! Along with the rest of the schooners in the Maine Windjammer Association, we will gather in Camden, Maine on the final night out our trip to join in on the festivities including a sail parade, passenger/crew talent show, live music and more. Camden is a community rich in Maritime history and culture, this homey, small town festival recognizes the part that these vessels play within that culture.
4 Night (Tues-Sat)
June 30 - July 6
Prices Starting at $1,940 pp
6 Nights (Sun-Sat)
The Great Schooner Race This lovely six night trip ends with a long-standing tradition, the Great Schooner Race! The first race was in 1953; On September 9th that year, Schooners Stephen Taber and Alice S. Wentworth raced neck and neck across Penobscot Bay. The day afterward, the Bangor Daily News reported, “Before the largest crowd in schooner racing history the Maine Coasting Schooner Championship was copped by the Taber by a mere four seconds in the most thrilling race held here in years.” It would be another 24 years before the next Great Schooner Race. In 1977, Captain Mike Anderson of Schooner Stephen Taber rekindled the Race. It's been a tradition ever since. Every summer since then, the Maine Windjammer Association has hosted the Great Schooner Race. It's a chance for all captains, crews and passengers aboard traditional vessels, from all over the Eastern Seaboard, to rendezvous for a fun day of racing. We celebrate the community of windjammers, we celebrate the tradition of sailing these fine, wooden ships, we celebrate sailing together and sharing our great state of Maine with our lucky guests. On this trip, we'll explore and wander around the bay for the first few days as usual, then meet up in Rockland Harbor for small boat racing fun and dinner under anchor with the fleet surrounding us. The next morning, the race is on! We head off on a scenic loop. While away, the breakwater will fill with onlookers. The return to the finish line is a fun parade! The day will finish off with an awards ceremony, music and celebration for all of our guests.
July 7 - 11
Prices Starting at $1,480 pp
4 Nights (Sun-Thurs)
Four Night Adventure Hosted by Marc Evan Jackson Marc Evan Jackson is an actor known for his roles on Brooklyn Nine-Nine, The Good Place, Parks & Recreation, The Baby-Sitters Club, and many more. He is one of the owners of GRACE BAILEY. Thirty years ago, long before he was in Hollywood, Marc was the first mate of the GRACE BAILEY's former sister ship, the schooner MERCANTILE. Marc is thrilled to be keeping the tradition alive, and can't wait to share the magic of schooners, windjamming, and Maine with old salts and newcomers alike.
July 12 - 16
Prices Starting at $1,480 pp
4 Nights (Fri-Tues)
Four Night Adventure Hosted by Marc Evan Jackson Marc Evan Jackson is an actor known for his roles on Brooklyn Nine-Nine, The Good Place, Parks & Recreation, The Baby-Sitters Club, and many more. He is one of the owners of GRACE BAILEY. Thirty years ago, long before he was in Hollywood, Marc was the first mate of the GRACE BAILEY's former sister ship, the schooner MERCANTILE. Marc is thrilled to be keeping the tradition alive, and can't wait to share the magic of schooners, windjamming, and Maine with old salts and newcomers alike.
July 23 - 27
Prices Starting at $1,480 pp
4 Nights (Tues-Sat)
Camden Classics Regatta For one day of this four night adventure, we will join in on the fun of the Camden Classics Regatta. Billed as “Excitement on a Historic Scale,” this regatta is “sailed where the mountains meet the sea, off the lovely harbortown of Camden, Maine.” Said to be “one of the world’s most beautiful regattas,” we’ll enjoy the show from the best seat in the house - out there sailing with them! Besides the regatta vessels, let’s not forget GRACE BAILEY. She’s a grand old schooner, long, lean and charming. built in 1882, we sail her with vigor and she still holds a stately line. She's well suited to the waters of Maine's midcoast and she's comfortably appointed for all aboard. This adventure will spark a love of sailing for newcomers. This trip will stir the passions of those keen on the salt life. It’s going to be great!
June 9 - 14
Prices Starting at$1,240 pp
5 Nights (Sun - Fri)
Schooner Gam, hosted by Marc Evan Jackson. Marc Evan Jackson, renowned actor from TV and movies is one of the owners of GRACE BAILEY. A Schooner Gam is a full fleet party; on this trip we'll tie up together with the whole Maine Windjammer Fleet and create a small, floating world. You will be able to explore the various vessels; a schooner party of all ships rafted together. The various musicians from the different vessels will gather and give you a show as well! The rest of the trip will be spent in the usual lovely pastimes of island hopping, sailing, eating good food, making friends and taking in the sights. All the windjammers dance around the waters of coastal Maine. We often criss-cross each other as we wander. It's a wonderful sight, each ship arcing by, guests waving their hellos. This gathering is to celebrate the unique living maritime culture of Maine; bringing the boats together so that you see them for yourself and celebrate with us, our sailor's life and the coast of Maine.
June 16 - 22
Prices Starting at $1,850 pp
6 Nights (Sun-Sat)
Sailing + Music: ft Tim Grimm with Friends Come enjoy this music trip featuring the world renowned folk musician, Tim Grimm who will be joined by a few guest musicians throughout the trip! Tim Grimm is a bit of a Renaissance man in the performing arts world, forging a rich and varied career that blends his love of songwriting, travel, and acting in theatre, film and television. For most of his 25-year career as a storytelling balladeer in the tradition of John Prine, Woody Guthrie, and Bob Dylan, Tim has written primarily about community, history, family, and social issues - often framed by his strong sense of place and the many years he spent on the family farm he built in rural Indiana. His songs are filled with rural characters and landscapes, written and sung with vivid warmth and intimacy. https://timgrimm.com/home
June 23 - 29
Prices Starting at $1,850 pp
6 Nights (Sun-Sat)
Western Wanderer On this trip, we set out to the lesser explored Muscongus Bay and Pemaquid Peninsula. We’ll head towards Boothbay. If conditions are favorable, we may even go to the Boothbay Windjammer Festival to visit the gathering of historic tall-ships. Join us for this wonderful wander west. Six nights is time enough for some great, far-flung adventures.

August

September

October

July
