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We board between 5 & 6 p.m. the night of your trip's start date. We arrive back in Rockland before noon on the day of your trip's end date. 

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GRACE BAILEY seen from VICTORY CHIMES Rockland.jpg

Sail

Grace Bailey

2023 Adventures

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

June 2023
JULY 2023
AUGUST 2023
SEPT 2023
Maine fog.jpg

Explore Secret Maine

SUN 3rd - SAT 9th

Standard Cabin Price $1,870 pp

6 Night Adventure

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Featuring Mike and Amy Aiken

SUN 10th - SAT 16th

Standard Cabin Price $1720 pp

6 Night Adventure

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Wooden Boat Sail-In Maine is celebrated for being the home of countless beautiful traditional wooden boats and rich and thriving Maritime culture. We’ll end this adventure by attending their annual “Sail In.” Vessels from all over come to celebrate the history and beauty of their chosen passion - wooden boats! This is your opportunity to get a full taste of this culture! The Wooden Boat School set in the beautiful Blue Hill region will host us along with other traditional boats for an afternoon of fresh local steamed mussels and live music. The rest of the week be full of as much sailing as we can squeeze in and all our usual good food and small boat fun!

SUN 17th - THU 21st

Standard Cabin Price $1410 pp

4 Night Adventure

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Hosted by Marc Evan Jackson

FRI 22nd - MON 25th

Standard Cabin Price $1210 pp

3 Night Adventure

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Hosted by Marc Evan Jackson

TUE 26th - SAT 30th

Standard Cabin Price $1395 pp

4 Night Adventure

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OCT
October 2023

MON 31st - THU 3rd

Standard Cabin Price $1250 pp

3 Night Adventure

FRI 4 - WED 9th

Standard Cabin Price $1650 pp

5 Night Adventure

Eggomoggin Reach Regatta The Eggemoggin Reach Regatta 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. This regatta is now often over a hundred vessels. It has grown to be a combination of two other local regattas, The Camden Feeder Regatta and the Castine Classic Yacht Race. It will be quite a sight. You will have the best seat in the house. The regatta is a wonderful way to punctuate this trip.

THU 10th - MON 14th

Standard Cabin Price $1410 pp

4 Night Adventure

TUE 15th - SAT 19th

Standard Cabin Price $1410 pp

4 Night Adventure

SUN 20th - THU 24th

Standard Cabin Price $1410 pp

4 Night Adventure

FRI 25th - MON 28th

Standard Cabin Price $1250 pp

3 Night Adventure

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.

SUN 16th - THU 20th

Standard Cabin Price $1410 pp

4 Night Adventure

FRI 21st - TUE 25th

Standard Cabin Price $1410 pp

4 Night Adventure

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

MON 5th - FRI 9th

Standard Cabin Price $1100 pp

4 Night Adventure

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SAT 10th - WED 14th

Standard Cabin Price $1250 pp

4 Night Adventure

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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. 

THU 15th - MON 19th

Standard Cabin Price $1210 pp

4 Night Adventure

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TUE 20th - SAT 24th

Standard Cabin Price $1385 pp

4 Night Adventure

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Featuring Tim Grimm

SUN 25th - SAT 1st

Standard Cabin Price $1750 pp

6 Night Adventure

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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.

JUNE

JUNE
2023 June
JULY
AUG
SEP

SUN 1st - WED 4th

Standard Cabin Price $1210 pp

Fall Foliage

4 Night Adventure

THU 5th - MON OCT 9th

Standard Cabin Price $1210 pp

Fall Foliage

4 Night Adventure

SEPTEMBER

OCT

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