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Day Sails Martha’s Vineyard


Discover the Magic of Martha’s Vineyard with a Personalized Sailing Adventure

 

Martha’s Vineyard is renowned for its picturesque towns, but there’s another side to explore — a serene, timeless sailing adventure that will captivate your senses. Each journey with us is thoughtfully tailored to your interests and desires, ensuring a unique experience every time.

From the deck of our sailboat, the stunning landscapes and harbors of Martha’s Vineyard come to life. Marvel at historic lighthouses still in operation, take in the breathtaking views of Vineyard Sound, the Elizabeth Islands and the North Shore, and witness the incredible diversity of wildlife. Whether you’re new to sailing or an experienced mariner, let the wonders of Southeast Massachusetts reveal themselves to you from the water, creating memories that will last a lifetime.

For those seeking something truly special, we offer customized arrival options to iconic locations on Martha’s Vineyard for our 3 and 6 hour options.  This allows a departure from one location and an arrival at a different harbor, which has the benefits of: the majestic feeling of arrival at a new location from the water, seeing more of Martha’s Vineyard in the same amount of time and visiting a new location.  Plan to visit a new port and maybe enjoy a meal.  Transportation is easily arrived to get back to the departure port after you have explored the selected location.  Some of the options include:

  • Edgartown – The combination of old world charm and wide open spaces. Many of the old whaling captains’ homes have been converted into inns, restaurants and and one-of-a-kind cafes and shops. Might want to check out the Mytoi Gardens, Wasque Wildlife Sanctuary, the Cape Poge and Edgartown Lighthouses and the Carnegie Museum.
  • Oak Bluffs – Is a vibrant town offering stunning miles of public beaches, unique shopping experiences, diverse dining options, ponds, several accessible parks, a busy seasonal waterfront and downtown district, a golf course, expansive hiking trails and rich arts and cultural offerings.
  • Menemsha – Is  a unique blend of cultural heritage and natural beauty. Known for its a historic fishing village that offers a picturesque harbor, fresh seafood, and amazing sunsets.  If you are seeking an authentic New England experience this is a must visit destination.

Other possibilities include exploring the Elizabeth Islands, Cuttyhunk, Falmouth, Hyannis, Nantucket, or Woods Hole, and if time permits, extend your adventure to delve even deeper into the beauty of the region.  Please note times may need to be altered due to the strong tides, if this is necessary we will contact you.

You’re welcome to bring your own food and beverages, making our sailboat the perfect setting for special gatherings and events. On longer voyages, enjoy lunch in a secluded cove, take a refreshing swim, or hike to landmarks like Naushon Island’s lighthouse. Whether you prefer to relax and soak in the scenery or actively participate by raising sails, steering, and learning the art of sailing, your journey will be as enriching as it is enjoyable.