CRUISE DESCRIPTIONS
Discover
Windjammer Cruises in Maine
Ready to take the leap
and join us?
CLICK FOR SPECIAL!
​While three days of sailing may not feel like quite enough, they offer the perfect opportunity for a memorable glimpse into life aboard a Maine windjammer. With scenic sails filled with fresh ocean breezes, Mary Day glides along the coast, revealing the quiet beauty of rocky shores, hidden coves, and charming harbors.
Each evening brings a new anchorage to explore, including a classic Maine lobster picnic on the beach—an experience as timeless as the coast itself. By day, take in the views from deck, lend a hand with the sails, or simply relax and let the rhythm of the sea carry you along.
And perhaps best of all, you’ll find camaraderie in the shared experience—new friendships formed with fellow shipmates along the way. It may be a short escape, but it’s one that stays with you.
Offered in June, July, August & September
$1360 per person
NEW for 2026!
Are you ready to sail, slow down and create something truly
your own?
4 Day Cruise
with Exclusive Optional Watercolor Retreat
Wake to the gentle motion of the sea and the quiet beauty of Maine’s coast unfolding around you. Aboard Mary Day, each day brings a new horizon—rocky islands, pine-lined shores, and hidden coves waiting to be explored.
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Fill your days as you choose: lend a hand with the sails, kayak along the shoreline, take a swim in a quiet anchorage, or stretch out on deck with a good book. Evenings bring shared meals, including a classic lobster picnic under the open sky.
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For those drawn to creativity, an optional watercolor experience with Maine artist Gianna Bird offers a meaningful way to engage more deeply with the landscape. Through guided instruction in sketching, pen & ink, watercolor washes, and color theory, you’ll learn to capture the light, movement, and character of the coast—whether you’re picking up a brush for the first time or returning to a long-loved practice.
June 16 - 20, 2026
$1450 per person
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Watercolor Retreat Add-On: $300 per person
(3 online classes and materials included)
Ready to check sailing a Maine windjammer
off your bucket list?
4 Day Cruise
No itinerary: Just sail & relax
Escape for four days of pure sailing, exploring, and relaxation along Maine’s breathtaking coastline. Perfect for a quick getaway, this shorter cruise gives you just enough time to unwind, enjoy the thrill of a traditional windjammer, and discover the hidden treasures of the coast without taking too much time away from home.
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Glide past rocky islands, quiet coves, and charming harbors as Mary Day carries you from anchorage to anchorage. Spend your days exploring by small boat, hiking ashore, swimming, or simply soaking in the scenery from deck. Delight in a classic Maine lobster picnic on a picturesque island and savor home-cooked meals shared with fellow travelers.
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With majestic sails, exceptional camaraderie, and just plain fun, this four-day cruise is the perfect introduction to life aboard a Maine windjammer. Adventure, relaxation, and memories await.
Offered in June, July, August & September
$1450 per person
Ready to fully immerse yourself in the rhythm of the tide and life aboard a Maine windjammer?
6 Day Cruise
An Immersive Windjammer Experience
​Join us as we unplug, unwind, and leave our cares ashore for six unforgettable days under sail. Three days are great, four days are better—but six days is the ultimate windjammer experience. Enjoy long, easy days of sailing, plenty of time to explore, outstanding windjammer cuisine, a classic Maine lobster picnic, and so much more. It’s hard to imagine a better way to experience the Maine coast.
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These six-day cruises are our simple, go-with-the-flow sailings, perfect for guests who want to relax and let the wind and tide set the pace. Unlike some of our other six-day voyages—which are tied to specific shoreside events—these trips remain wonderfully unstructured, with only gentle themes such as:
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No Smoking Cruise
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Captain’s Favorite Harbors
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Perseid Meteor Shower.
Unplug, settle in, and enjoy life under sail. Let’s go sailing!
Offered in June & August
$1798 per person
Ready to experience the camaraderie of a
Maine windjammer gam?
CLICK FOR SPECIAL!
A "gam" is a gathering of sailing vessels for socializing and celebrating maritime tradition.​
June is a wonderful time to explore the Maine coast, with its extended daylight and serene beauty before the height of summer. This four-day cruise follows the tradition of classic windjammer voyages, offering leisurely sails, quiet coves, charming harbors, and the timeless rhythm of life at sea. The highlight of the season is the inaugural windjammer fleet gathering, or “gam,” where you can witness the largest assembly of working commercial sailing ships on the Atlantic. During this unique event, guests can move between schooners, enjoy live music, and experience the camaraderie of the windjammer community—all as part of a traditional coastal adventure. The gam is an exciting addition to the journey, making this cruise a rare opportunity to combine the classic pleasures of sailing with a truly extraordinary maritime celebration.
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June 7 - 11, 2026
$1450 per person
Are you ready to see Maine's wild coast -
and capture it in a
whole new way?
6 Day Cruise
Natural History & Photography
Learn to see—and capture—the joy of nature while sailing through Maine’s pristine island archipelago, rich with wildlife and shaped by dramatic coastal geology. From magnificent megafauna to the smallest details of flora and shoreline textures, this six-day adventure invites you to slow down and truly observe the natural world.
Bring your camera and binoculars as award-winning photographer Jim Dugan and a knowledgeable guest naturalist, Merrie Ely, join us on board. Together, they’ll guide you in making the most of any camera—even a smartphone—while helping you understand how light, timing, and perspective transform what you see into something unforgettable.
As we explore Maine’s vibrant coast, you’ll discover both the grand and the subtle—from seabirds in flight to the intricate patterns of tide and stone. With the longest days of the year as your backdrop, there’s ample time to immerse yourself in nature, refine your eye, and capture moments that feel both fleeting and timeless.
Come celebrate the season, the light, and the beauty of the natural world—one frame at a time.
June 7 - 11, 2026
$1898 per person
What's it like to race among a fleet of traditional schooners - ready to find out?
6 Day Cruise
Great Schooner Race
Get ready for an unforgettable experience unlike any other. Join us for a spectacular gathering of traditionally rigged sailing vessels and their spirited crews, coming together for one of the most exciting events on the Maine coast.
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The festivities begin with the lively small boat regatta, where crews and guests alike take to the water—paddling, rowing, and sailing a colorful array of craft in a celebration of skill and camaraderie. Then comes race day, when the energy builds and the fleet sets sail, navigating the bay in a thrilling contest of wind, strategy, and seamanship.
Aboard Mary Day, you’re not just a spectator—you’re part of the crew. Help trim the sails, take a turn at the helm, and cheer alongside your shipmates as the race unfolds. With past victories under her belt, Mary Day always sails with spirit—but every race brings new excitement.
Come be part of the tradition, the teamwork, and the exhilaration—and create memories that will stay with you long after the sails are lowered.
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June 28- July 4, 2026
$1925 per person
Join us to see Maine's lighthouses from the water and uncover the stories they've guided for generations.
6 Day Cruise
A Lighthouse Journey
Experience the magic of Maine’s coast through its most iconic landmarks on this unforgettable lighthouse journey aboard a traditional windjammer. Sail past rugged shores and quiet islands as these historic beacons come into view—each with its own story, guiding mariners safely home for generations.
While lighthouses grace many of our voyages, this cruise offers a deeper appreciation, with countless opportunities to view and photograph them from the ever-changing perspective of the sea. With more than 20 lighthouses scattered throughout our sailing grounds, each day brings new sights and stories to discover.
Enhancing the experience, a lighthouse expert joins us on board, sharing fascinating history, local lore, and insights into the lives of the keepers who once tended these lights. From deck, you’ll gain a richer understanding of their purpose and presence along the coast.
Be warned—once you begin spotting them, you may find yourself happily hooked. Join us and experience the Maine coast one lighthouse at a time.
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Offered in July & September
$1898 per person
Are you ready to sail Maine's coast, savor a lobster picnic and join the excitement of the Windjammer Festival?
6 Day Cruise
Camden Windjammer Festival
Begin your adventure sailing along Maine’s breathtaking coastline aboard a traditional windjammer, where each day brings new coves, islands, and harbors to explore. Relax on deck, take a swim, or explore ashore by small boat, and savor a classic Maine lobster picnic in a picturesque anchorage—true windjammer tradition at its finest.
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After days filled with the rhythm of sails, home-cooked meals, and the camaraderie of life at sea, the journey concludes in Camden for the Windjammer Festival, celebrating the founding of the windjammer tradition in 1936. Enjoy concerts, captivating events, a thrilling schooner talent show, and a spectacular fireworks display over the harbor.
Join us and the fleet for a majestic parade of sail into Camden, bringing together windjammers old and new for an unforgettable celebration. The weekend is packed with family-friendly fun, offering something exciting for both kids and adults alike. Come experience the sails, the flavors, and the festival spirit—this is Maine windjammer life at its best!
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August 30 - Sept. 5, 2026
$1750 per person
Ready to experience Maine's coast and celebrate its iconic Windjammer fleet?
6 Day Cruise
Wooden Boat Rendezvous
Join us for the final gathering of Maine’s tall-ship fleet at the historic home of WoodenBoat Magazine—just one unforgettable day of your windjammer adventure. Spend time ashore exploring the WoodenBoat School’s workshops, charming gift shop, and scenic grounds. Watch skilled craftsmen at work, stroll the picturesque grounds, and soak in the maritime atmosphere.
The rest of your trip is spent sailing Maine’s beautiful coast aboard a traditional windjammer, with quiet coves, scenic islands, and classic lobster picnics along the way. With majestic sailing vessels gracing the Maine coast, you’ll have endless opportunities to capture breathtaking photos and memories. Don’t miss this chance to celebrate the summer in true windjammer style!
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September 13 - 19, 2026
$1750 per person
Ready to host a reunion, celebration, or adventure that no one will ever forget?
Group Charters
Are you looking for the ultimate venue to host an unforgettable family reunion, sailing club outing, alumni gathering, or graduation adventure? Look no further than Mary Day, the perfect setting for your special occasion.
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Aboard this beautifully rigged Maine windjammer, we offer tailored sail training cruises designed for your group’s interests. Whether you’re seeking action-packed sailing, team-building experiences, or simply quality time together, you’ll immerse yourself in an unforgettable, hands-on adventure that combines skill, camaraderie, and fun.
Planning a family reunion, wedding, or getaway with friends? We take care of the cooking, cleaning, and logistics, so you can focus on making memories on deck and ashore.
Call us today to explore your options and let us help you create a truly remarkable group experience at sea!
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Available May - September
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Best booked year in advanced
Call 800-992-2218
