We all know summer gets busy here, and it’s easy to let the season slip by without ever getting away. And now with travel delays, higher gas prices, and crowded destinations, sometimes getting away can feel like more trouble than it’s worth.
But you don’t have to go far to find something different. Make this the summer you finally take a SAILcation on one of Maine’s historic windjammers!
Treat yourself to a few days aboard a traditional schooner sailing through Maine’s protected bays to the quieter, lesser-known islands. You’ll have time to spot wildlife, explore islands, and reconnect with Maine’s outdoors away from the summer crowds.
We’ve set aside a limited number of cabins on select trips at special Maine resident rates (see below). It’s just our way of making it easier for locals to get out on the water with home-cooked meals and time to truly unwind for a few unforgettable days. Availability is limited, and offers may change, so if you’ve always meant to go, this is your moment.
Your cruise fare covers the entire experience: the sailing, all home-cooked meals, hors d’oeuvres, and desserts, and your private cabin aboard a historical schooner. Shore excursions—including the beloved island lobster bake—are included, with no hidden fees or extra charges along the way.
Featured Trips
Windjamming on the FRENCH means going out into jaw-droppingly beautiful Mid-Coast Maine on a traditional (National Historic Landmark) schooner for several days and nights at a time. It means being engaged with sail-handling, anchor cranking, meaningful conversation, and lots of great food cooked on a wood stove by the crew. It means sleeping onboard a beautifully maintained antique boat in your own cozy cabin, followed by lovely mornings on deck with coffee or tea in hand. No better place in the world to read a book, if you want a break from enjoying the view, the food, the sailing, and the company. We’ll sail the breezes in pursuit of Lobster Bake Island and an awesome place to drop anchor so we can watch the sun set and the stars come out! More info at www.schoonerfrench.com.
Celebrate the 4th of July aboard the Schooner Heritage as we head out sailing for lobsters on the beach, and festive music aboard. Later in the week we’ll meet up with a dozen other historic vessels for contests of speed and skill, culminating with a great race amongst the windjammer fleet. After the race, more celebrations with food, awards, and more music! Learn more at www.schoonerheritage.com.
Call 207-701-5036 to book.
Some adventures need more time, and six nights gives you just that. Sail aboard the Grace Bailey, one of the original windjammers and a National Historic Landmark, and feel the difference that an extra day or two at sea can make.
With more time, comes more to discover. Venture beyond Penobscot Bay to explore remote islands, spot abundant wildlife, and settle into the unhurried rhythm of life under sail. No rushing from port to port, just fresh salt air, delicious home-cooked meals, and the freedom to truly unwind aboard a living piece of American maritime history. Learn more at www.SailGraceBailey.com or call (207) 691-9521.
Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings. www.schoonerheritage.com
Call 207-701-5036 to book.
Kate Shaffer, acclaimed chocolatier, author and co-owner of Ragged Coast Chocolate in Westbrook will be joining us for this extravaganza of chocolate tastings and desserts. More info at www.stephentaber.com or call 207-594-4723
Join us for a one-of-a-kind lighthouse experience, enhanced by a lighthouse expert on board. Discover the rich history and beauty of these iconic coastal beacons from the same waters that guided mariners centuries ago. With 23 lighthouses in our sailing area, you’re sure to encounter many along the way—and you may just find them delightfully addictive. Visit www.schoonermaryday.com or call (207) 785-5670.
Take a break from summer for a restorative and relaxing 4-night sail! This is an all-levels yoga, meditation, breathwork, and sailing experience. Certified yoga instructors will lead yoga and wellness workshops daily. Enjoy creative healthy meals to support your body and soul. More info at www.SailAngelique.com or call 1-800-282-9989.
Some adventures need more time, and six nights gives you just that. Sail aboard the Grace Bailey, one of the original windjammers and a National Historic Landmark, and feel the difference that an extra day or two at sea can make.
With more time, comes more to discover. Venture beyond Penobscot Bay to explore remote islands, spot abundant wildlife, and settle into the unhurried rhythm of life under sail. No rushing from port to port, just fresh salt air, delicious home-cooked meals, and the freedom to truly unwind aboard a living piece of American maritime history. Learn more at www.SailGraceBailey.com or call (207) 691-9521.
Join Kike Calvo, award-winning photographer and National Geographic educator, for an unforgettable hands-on workshop aboard the historic Stephen Taber. Whether you’re a seasoned photographer or simply want to connect more deeply with your creative eye, this expedition invites you to slow down, observe, and create with intention. Visit www.stephentaber.com or or call 207-594-4723.
Even if you can only get away for three-nights, you’re sure to feel refreshed and relaxed aboard LADONA. www.schoonerladona.com or call 207-542-5958.
Let us wine and dine you while you relax on board. www.schoonerladona.com or call 207-542-5958.
Don’t work your summer away! This trip is the perfect weekend sailing adventure before the summer is behind us. The best introduction to windjamming! Enjoy delicious scratch cooking, soak up the sun on deck, and marvel at the iconic Maine coastline as we sail through Penobscot Bay. More info at www.schooneramericaneagle.com. 207-701-5037.
We’ll participate in a parade of sail as the schooners return to Camden Friday evening. You’ll have the best seat in town for enjoying the schooner crew talent show, live music, harborside dancing and other festivities in town. Guests disembark Saturday after breakfast. Schoonerfrench.com or 207-542-1241.
At the end of this cruise, the RIGGIN and other Maine Windjammers will create a Parade of Sail outside Camden Harbor before docking in Camden to enjoy the Festival. Festivities include a Schooner Crew Talent Show and Live Music with dancing on Friday evening. Festivities continue all weekend. More info at www.schoonerriggin.com.
Call 207-594-1875 to book!
Join us for a one-of-a-kind lighthouse experience, enhanced by a lighthouse expert on board. Discover the rich history and beauty of these iconic coastal beacons from the same waters that guided mariners centuries ago. With 23 lighthouses in our sailing area, you’re sure to encounter many along the way—and you may just find them delightfully addictive. SchoonerMaryDay.com or (207) 785-5670
You won’t want to miss this historic occasion to celebrate boatbuilding and seamanship!
One night we will sail into the harbor in Brooklin, Maine, home of the WoodenBoat School, store, and magazine. This fall gathering of the Maine Windjammers marks the last of the sailing season and includes refreshments from local sponsors, live music & dancing, and tours of the WoodenBoat grounds. Nowhere else in the world can you see this many historic schooners under sail together. www.schoonerriggin.com
Call 207-594-1875 to book!
A perfect trip for a short adventure on the water. Come see the foliage change from its most striking side, the ocean! Between our galley woodstove and our main cabin stove feeding our cabin hallway radiators, there is no shortage of warmth aboard. Fall sailing in Maine is stunning. Learn more at www.schooneramericaneagle.com. 207-701-5037.
Windjamming on the French means going out into jaw-droppingly beautiful Mid-Coast Maine on a traditional (National Historic Landmark) schooner for several days and nights at a time. It means being engaged with sail-handling, anchor cranking, meaningful conversation, and lots of great food cooked on a wood stove by the crew. And at this time of year, the changing foliage colors add an extra delightful backdrop.
To reserve, visit SchoonerFrench.com or call 207-542-1241.
Please note: All trips must be booked via the individual Windjammer’s website or by giving them a call. Not combinable with any other offers. Discounts only for Maine residents.
