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, so if you’ve always meant to go, this is your moment.
Featured Trips
Early summer is a magical time to sail Maine’s coast. Harbor seal pups born in May can be spotted learning to swim, while nesting coastal birds fill every cove with activity. Beat the summer crowds and experience the coast at its most peaceful, before the busy season sets in. More info at www.SailAngelique.com.
These trips are a wonderful combination of sailing and exploring. Guests will get to explore some of the great hiking trails we have discovered. After or before sailing each day, we’ll take advantage of the long June days and head ashore for a hike. Hikes of different lengths and levels can be arranged. All hiking is optional. More info at www.schoonerfrench.com.
While three days of sailing may seem brief, it’s the perfect way to experience a taste of life aboard a Maine windjammer. With evening stops in charming harbors, a lobster picnic on the beach, and days filled with fresh breezes under sail, Mary Day glides along the coast, eager to share the many treasures of coastal Maine. Along the way, new friendships are sure to form. We’re ready—are you? Join us!More info at www.schoonermaryday.com.
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.
We’re venturing beyond our usual Penobscot Bay sailing grounds for something special. Mid-week we’ll arrive in style by sea — skipping the summer traffic and sailing straight into the heart of the festivities.
The Windjammer Days Festival carries extra meaning in 2026, celebrating both the nation’s 250th anniversary and the 250th birthday of the U.S. Navy. Come ashore for a traditional New England lobster bake on Cabbage Island, explore the picturesque town, browse unique shops, and mingle with locals and fellow sailors from vessels near and far. Cap the evening watching fireworks light up the harbor — the perfect end to an unforgettable sail.
The other evenings of the trip still include anchoring in beautiful secluded harbors, days of great sailing and island exploration. Learn more at www.schoonerheritage.com.
Call 207-701-5036 to book.
Race aboard the winner of the only Oyster Schooner Race ever held on the Delaware Bay!
Join us on this 6-day, 6-night adventure for stunning visuals of historic schooners sailing along Maine’s iconic rocky coast. On Friday we’ll participate in Great Schooner Race, providing an opportunity for captains, crews and guests aboard traditional vessels from all over the Eastern Seaboard to rendezvous for a day of racing.
The evening before the Great Schooner Race, crew and guests from participating boats can indulge in a zany, character-filled race complete with costumes and themes. It’s a time-honored tradition – and if you’re lucky enough to be sailing on one of the nine vessels of the Maine Windjammer Association – it’s an absolute riot! More info at www.schoonerriggin.com
Call 207-594-1875 to book!
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.
Let the waves, wildlife, and magnificent scenery mesmerize you. Daylight hours are spent sailing among untouched islands and exploring ashore, evenings are filled with easy camaraderie and hearty dinners, and quiet nights are free from the sound of traffic. More info at www.stephentaber.com.
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.
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.
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.
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.
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.
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!
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.
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.
