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You may think you’ve already seen the coast of New England, but we can guarantee you’ve never seen from the deck of a windjammer. A windjammer cruise in Maine offers a rare opportunity to sleep, dine, and be entertained while island hopping throughout Downeast and Midcoast Maine on a one-of-a-kind vintage vessel.

Maine is home to the country’s largest collection of historical sailing vessels which make up the Maine Windjammer Association fleet. The nine vessels in the fleet of traditionally-rigged sailboats offer overnight guests the opportunity to see Maine from an unforgettable perspective. All vessels in the fleet are independently owned and operated and many are National Historic Landmarks, with some hailing from the late 1800s and some built more recently. Each has a storied history with distinct characteristics and a unique layout, all of which your captain will be excited to share details of during your journey.

Concerned about the environmental impact of cruising? Take comfort in knowing that taking a windjammer cruise in Maine is a more sustainable way to travel than driving or cruising on a large ship. Many of the vessels in the fleet do not have engines and those that do use the power of wind as often as possible. Not only does windjamming in Maine offer a more earth-friendly adventure, but you will be able to explore more harbors due to the smaller vessel size.

A traditional trip from MidCoast Maine

Set sail from either Rockland or Camden, which are two of MidCoast Maine’s beautiful coastal towns. Choose from two to ten-night cruises which sail from late May through Mid-October. Some have specific agendas, such as attending a festival, participating in a race, or gathering with other vessels for a special event, yet most offer an unscripted journey along the coast where the captain charts each day’s sail based on the water and the wind. Because of this, a rough day at sea is rare.

Windjammer Days Festival

Our six-night adventure aboard the Angelique took us down the coast of Maine to Boothbay Harbor for the 60th annual Windjammer Days Festival. Alongside two other Maine Windjammer Association vessels, Heritage and American Eagle, we carefully zig-zagged our way into the harbor for the festival’s gathering of the fleet. A crowd of spectators cheered from the shore, snapping pictures as the windjammers made their entrance and took center stage. A fife and drum band atop a day-tour boat serenaded us as we anchored in the harbor for this mid-week event. Boats filled with enthusiastic festival goers circled around us for an up-close look at the impressive vessels.

The week-long festival, held each year at the end of June, celebrates maritime history with activities on-shore and off. A variety of events for visitors of all ages take place throughout the week including a lighted boat parade, a crab cake cookoff, a pancake breakfast, cannon lessons for young pirates, a lobster eating contest, cod fish races, and daytime and sunset sails for those not quite ready to dive into an overnight excursion on a windjammer. There is truly something for everyone.

The 2022 festival celebrated the women of the working waterfront in honor of the festival’s founder Marion Dash, who was the first woman on the Maine coast to receive a captain’s license. Kim Gillies, a volunteer committee member with the Windjammer Days Festival, shared that Windjammer Days was born when Marion and her husband, captain David Dash noticed a gathering of windjammers tucked into the harbor, patiently waiting for the fog to lift so they could safely return to sea. From that point on, Marion and David decided to welcome windjammers from across New England to gather in the harbor each year.

After the windjammers had their moment of glory arriving in the harbor, the festivities shifted shoreside to the parade that worked its way through town. Guests aboard the windjammers got to continue the pomp and circumstance with a row to shore to stretch our seafaring legs, do some shopping, and watch the parade. We felt like movie stars walking the red carpet as we stepped onto the dock and headed into town. Being part of the exclusive group of visitors arriving at the festival by windjammer is a highlight of a windjammer cruise in Maine.

It had been 25 years since the Angelique sailed into the festival with her guests since the Maine Windjammer Association vessels take turns participating each year. As part of the festival celebration, guests aboard the windjammers were also invited to attend the Cabbage Island Lobster bake the night prior for an unforgettable feast of lobster, chowder, steamers, corn on the cob, baked potatoes, and blueberry cake. The day’s events ended with an epic sunset followed by a firework display out in the harbor. Of course, the windjammer guests got the best seats in the house.

While onboard, embrace doing little or a lot — you choose

When you board your vessel and set off on your cruise, be prepared to exchange your day-to-day routine and life responsibilities for a decision-free trip. Your captain and crew have all details covered, from accommodations, to food, to sightseeing, and more. While you won’t be required to check your cell phone at the dock when you arrive, you will want to switch it off and forget the rest of the world as you take in the joys of sailing.

Settling into life on board, you will discover that you can do as little or as much as you wish each day. If you’re feeling energetic, you can help the crew raise and lower the sails and rowboats or even help prepare meals. If you just want to relax, simply let the days pass by while lounging on the 95-foot deck with a good book, or pop down to your cabin to nap whenever you wish.

Below deck on the Angelique are 15 guest cabins, each with a private sink plus ample linens and towels. There is plenty of headroom to stand in your cabin before settling into bed. Guests share three “heads” located throughout the boat which include toilets and freshwater showers. Another shower on the deck offers the opportunity to rinse off after a day at sea.

If you’ve come to Maine hoping to see wildlife, you are in luck. While on board, be on the lookout for seals sunbathing on the islands, porpoises swimming alongside the boat, whales spouting out in the distance, and bald eagles nesting in pines along the coast. Feeling a bit dare-devilish? Jump off the bow for a refreshing cool down on hot summer days while the windjammer is anchored. For a slower-paced adventure, hop on a paddle board and explore the area.

Who knew you could eat so well on a Windjammer cruise in Maine?

While each day unfolds spontaneously, one experience is guaranteed, you will be well fed. Wake up to the aroma of freshly brewed coffee followed by blueberry pancakes and smoked bacon for breakfast. Homemade soup and salad alongside fresh-baked bread will satisfy your lunch cravings but make sure you save room for “lunch dessert.” As evening sets in, prepare for appetizers followed by dinner and dessert (again), which might include ice cream made by the captain himself. Don’t worry about missing a meal, because the sound of the chef ringing the dinner bell will grab your attention as he announces what he has prepared.

The daily farm-to-boat dining experiences all feature food sourced from local farms. A windjammer cruise in Maine is not complete without lobster, which you will get to enjoy at a traditional Maine lobster bake included on your cruise. Your captain will drop anchor near one of Maine’s 2000-plus islands where the crew will prepare this unforgettable feast.

The excursions are just as fun as the sailing

The island lobster bake is just one opportunity to step off the boat. As each day’s course unfolds, your captain will choose villages to visit along the state’s 3000-plus mile coastline. A quick row to shore and you’ll be off sightseeing, shopping, or grabbing ice cream from a local business. If you want to get some steps in, hike through the pines along one of the state’s many coastal trails. You might even get to search for sea glass or the perfect shell at a nearby beach. Back on board and before settling in for the night, your captain will invite you to gather around a map to share details and answer questions about the day’s sail.

Embrace the slowness of windjammer cruise in Maine

As evening sets in, embrace the slow pace of the vessel and enjoy a front-row seat to a 360-degree sunset. While the sky transforms, you’re free to choose how to wind down for the evening. Gather with new friends below deck for an evening of cards and board games. Or cozy up on the deck with a blanket while a crew member plays guitar or piano in the deckhouse (if you’re on the Angelique). Soak in the magic of the whole experience as you gaze at the dark night sky and get lost in the stars before heading down to your cabin.

You’ll share the experience with only a few travelers and an exceptional crew

As you embrace the slow pace of the journey, you will get to know the like-minded adventurers onboard with you. Vessels in the fleet vary in size, carrying between 16-40 guests along with four to 10 crew members. Your sailing family is likely to be an energetic, well-traveled group, spanning decades in age. Many guests are likely to be repeat customers who have fallen in love with windjamming. These well-seasoned guests appreciate the opportunity to disconnect from the outside world and spend time in nature while learning skills that can’t be learned elsewhere. Most live outside of Maine and choose to seize the opportunity to experience the state in a unique way. First-time windjamming guests take comfort in knowing that many fellow guests keep coming back year after year (like some of those aboard Angelique who were back for their 17th and 39th cruises!)

Captain Dennis and the crew aboard the Angelique thrive on watching life-long friendships form as stories are shared and connections are made. While guests arrive happy to be on vacation, the crew excels at keeping this energy flowing. They want their guests to have unforgettable experiences. Their love for sailing and Maine are evident, as they tell stories and answer questions about the history of sailing, the names of islands, the legends of lighthouses, and more.

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