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Windjammer Cruises in Maine



June, July, August, and September

While 3 days of sailing may not be long enough, they do offer a chance for a quick glimpse of sailing on a Maine windjammer. With stops every evening, lobster picnic on the beach and days of sails filled with breeze, Mary Day will ease along the coast eager to share all the treasures of coastal Maine. And not to forget, new friendships made along the way. We’re ready! How about you? Join us!’





June, July, August, and September

Join us for 4 days of simply just getting away to enjoy sailing, exploring and relaxing. Let us take you along the coast, show you the hidden treasures that Maine has to offer. Take time to explore the anchorages by small boats. Enjoy a lobster picnic while touring the island. Sail on a windjammer with majestic sailing, great food, exceptional camaraderie and just good ole plain fun! Ready to go? Join us!






Escape the hubbub with an authentic sailing getaway with no itinerary, just pure bliss and pure fun. Feel the breeze on your face, hear the seals barking, smell the fresh salt air. Enjoy scrumptious windjammer cooking, island lobster picnic and countless explorations of islands, wildlife, and the amazing world you live in. Don’t miss out on the magic of the Perseid Meteor showers! So hit your restart button and getaway! Join us!





June, July, August, and September

Join us as we unplug, unwind and leave our cares ashore for 6 days! 3 days are great, 4 days are better and 6 days is the ultimate cruise! Enjoy endless sailing, tons of exploring, amazing windjammer cuisine, lobster picnic and oh so much more! Can you tell this is cool way to explore Maine? While some of our 6-day trips are just plain old "sit back, relax with no itinerary" cruises, some have events planned during the trip so be sure to read on. You don’t want to miss out in all the fun! Let’s go sailing!





June and September

Join us for four days of a unique lighthouse tour under sail aboard the Maine windjammer Mary Day. Live the history of these magnificent coastal sentinels from the perspective of the mariners that used these lighthouses a hundred years ago. Of course, we see lighthouses on every cruise, but this is your chance to see firsthand the magnificent scenes you just can’t view from shore. Come aboard as we showcase these spectacular national treasures, hear their stories of fact and fiction, see their beauty and feel their ruggedness as we sail by. With 23 lighthouses in our sailing area, we can assure that you will see many of these coastal icons. It is always our goal to tour the inside of an actual working lighthouse, weather depending as Mary Day is a pure sailing vessel. Warning: lighthouses can be addicting! Join us and see how!






A spectacle not seen anywhere else in the world: an amazing congregation of traditionally rigged sailing vessels as well as captain’s egos. The event takes place over two days with the infamous small boat regatta kicking off the evening prior to race day. Enjoy the antics of crew and passengers as they gallantly paddle, row or sail in an assortment of floating crafts. Race day follows with a full day of large vessel sailing, tacking in and out of each other as they head down the bay jousting to be first to cross the line.  Mary Day has won a number of times but has been bested enough to make it a great race. Come and join us! Help us tack the sails, steer and cheer as we cross the finish line. It’s a team event and we would love for you to be a part of our crew!





This one is for those who just can’t get away or unsure what windjamming is all about. It’s our “teaser” cruise. Join us for one night under the stars and two days of fun in the sun.  Hop on in the morning and we’ll depart shortly thereafter for a fun day of sailing on the bay. Your days will be spent helping out with sailing or kicking back and feel  the breeze. It’s your two days to enjoy.  We’ll tuck ourselves into a quiet cove for the night. While at anchor take time to go off for a row, paddle, hike on shore or simply beachcomb along the shore. Plenty of stars overhead at night to admire while you listen to the quiet night, away from the hustle onshore that awaits you once again. Windjamming is not for everyone and we get that. Here’s your chance to give it a try! Join us!






Learn to capture the joy of nature and enjoy the thrill of sailing Maine’s pristine island archipelago rich with wildlife (magnificent megafauna!) and textured by dramatic island geology. Grab your camera and binoculars for this 6-day adventure as we bring along award winning photographer Jim Dugan as well as a guest naturalist. Having both talents on board you will see what is possible with the very modest camera (or cell phone) and how light plays an important role as we explore and appreciate the mega and micro fauna and flora of Maine’s naturally vibrant coast. These are the priceless moments to capture. Celebrate with us the longest days of the year and seize the light!






We invite you for a week of experiential instruction aboard one of Penobscot Bay’s legendary tall ships. Designed and rigged along the lines of a traditional coasting schooner, (with added comfort and safety in mind), Mary Day majestically carries 5,000 sq. ft. of canvas, more sails than any other schooner on the bay. Come and take part in the “hands-on” adventure and become an integral member of the Mary Day crew and see what it takes to sail a traditional schooner. Fret not, we still call it a vacation! We’ll sail, play schooner, explore the islands and enjoy good food and great company. So, grab your gear and plan on getting your hands dirty! Join us!




the festival for 2021 has been cancelled,
but fear not!
The Maine Windjammers plan to gather! 


For 2021 Sailing Season: The Maine Windjammer Fleet will create a parade of sail as all the vessels anchor together in a harbor for an evening of fleet camaraderie. Crews (and guests!) can participate in small boat races and maritime shenanigans. This is a great opportunity to see all the vessels up close!

For 2022 Sailing Season: The Camden Windjammer Festival celebrates the 1936 founding of the windjammer industry right here in Camden with concerts, plays, a schooner talent show, as well as fireworks. We will join the other windjammers in a parade of sail into Camden where we all raft up for the evening festivities. The Camden Windjammer Festival weekend events are family oriented with fun activities for kids and adults.






Celebrate the season’s final gathering of Maine’s tall-ship fleet at the home of Wooden Boat Magazine. Come join us as we converge in a parade of sail into the harbor at Wooden Boat. There will be time ashore to explore Wooden Boat School’s workshop, gift store and beautiful grounds for a leisurely walk while seeing craftsman at work at the school. Big, beautiful sailing vessels with a Maine coast backdrop will create many great images for you to capture. It’s a great way to end a summer so join us as we tip our hats off to celebrate!



1.GROUP CHARTERS.Family Charter .jpg



Looking for a venue to host a family reunion, sailing club outing, alumni gathering, or even a graduating class trip? Mary Day is the perfect place to gather! Aboard Mary Day we offer sail training cruises for school groups and for adults with each trip tailored directly to each group’s interest. Spend your days learning the skills to sail a traditionally rigged vessel through team building and leadership skills. This is an exciting, active, experiential vacation! Or perhaps your thinking of hosting a family reunion, wedding or a group of friends? Let us worry about the cleaning, the cooking and take the time to enjoy your company in a setting all can enjoy. Give us a call and we will be happy to discuss chartering options and help you craft the perfect solution to all your needs!