Below is the schedule of our Maine sailing adventures for 2023, All trips depart from Rockland Maine. 

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.

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.

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.

Five Night Adventure Join us for a longer trip in the height of the Maine summer sailing season!

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!

Three Night Adventure Three night adventure sailing throughout Penobscot Bay! This trip is in the heart of the sailing season, with the most beautiful summer days and the water in the bay warming up just enough for a swim. Come join us!