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

Explore Secret Maine
SUN 3rd - SAT 9th
Standard Cabin Price $1,870 pp
6 Night Adventure
Featuring Mike and Amy Aiken
SUN 10th - SAT 16th
Standard Cabin Price $1720 pp
6 Night Adventure
Wooden Boat Sail-In, Featuring The Chivalrous Crickets
SUN 17th - THU 21st
Standard Cabin Price $1410 pp
4 Night Adventure
Hosted by Marc Evan Jackson
FRI 22nd - MON 25th
Standard Cabin Price $1210 pp
3 Night Adventure
Hosted by Marc Evan Jackson
OCT
THU 10th - MON 14th
Standard Cabin Price $1410 pp
4 Night Adventure
Featuring Louisa Stancioff
TUE 29th - SAT 2nd
Standard Cabin Price $1495 pp
4 Night Adventure
Camden Windjammer Festival 4 night island hopping and exploring punctuated by the Camden Windjammer Festival. This long-standing tradition is fun for everyone featuring a crew and passenger talent show from all the Schooners. With live music and vendors, this homey small town festival focuses on honoring our celebrated and loved local sailing culture. Maine is a community rich in Maritime history and culture.The Camden windjammer festival is our community's recognition of the part that these vessels play within that culture. The quaint seaside town of Camden will welcome us to their harbor for an evening of fun events including the annual crew talent show, not to be missed! The rest of your week will be spent sailing and exploring islands. You will get a real taste of what the story of Maine has to offer.
AUGUST
SUN 2nd - SAT 8th
Standard Cabin Price $1850 pp
6 Night Adventure
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!
SUN 9th - SAT 15th
Standard Cabin Price $1850 pp
6 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. 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.
WED 26th - SUN 30th
Standard Cabin Price $1495 pp
4 Night Adventure
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!
JULY
SAT 10th - WED 14th
Standard Cabin Price $1250 pp
4 Night Adventure
Schooner Gam: hosted by Marc Evan Jackson A Schooner Gam is a full fleet party; it's when we tie up together and create a small, floating world. We’ll end out trip with this friendly get-together. All the windjammers dance 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 time out, for one of the evenings on this adventure, the full fleet of schooners will gather and tie up to one another. "Schooner Party" explains it nicely. Maine is one of the only places in the world where you can see 12 Schooners of this magnitude in the same harbor. 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. 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 magical experience of gathering together on deck while the music wafts through the harbor is a truly unforgettable memory. Join us for this doubly-special trip. 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.
SUN 25th - SAT 1st
Standard Cabin Price $1750 pp
6 Night Adventure
Western Wanderer On this trip, we set out to the lesser explored Muscungus Bay and Pemaquid Peninsula. We’ll head towards Boothbay. If conditions are favorable, we may even go to the Boothbay Windjammer Festival. We always follow the best conditions, so the festival isn’t a sure thing, but a good time no matter what or where is. Join us for this wonderful wander west. Six nights is time enough for some great, far-flung adventures.