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

Great Schooner Race This lovely six night trip ends with a long-standing tradition! It would be enough to just explore the Maine coast by sail, visiting islands along the way, enjoying scenic coves at night, and being spoiled with fine meals along the way - BUT this trip has even more - 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 all explore and wander as is our lucky habit, then we'll all meet up Rockland Harbor. There we'll have small boat races with both crews and guests joining in. 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!
 Six Night trips are always great fun. This one ends with a real topper - a meeting of the fleet and a race to the finish!
 The only planning you need to do for this vacation is to plan on having a great time!

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. 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.

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! The regatta is only one day of this trip. The other days will be filled with “regular” windjamming; the enchanting exploration of Maine’s coastal archipelago. If you've never been sailing or even been to Maine, why not start with this all-out montage of sailing beauty? 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!