Top 6 Sailing Charters on Martha’s Vineyard

September 18, 2023

Nestled amidst the pristine waters of Martha’s Vineyard lies a paradise for sailing enthusiasts and adventurers. Martha’s Vineyard, renowned for its natural beauty and coastal charm, offers an idyllic backdrop for unforgettable sailing experiences. Whether you’re a seasoned sailor or a landlubber eager to embark on a maritime adventure, sailing charters on Martha’s Vineyard have something special in store for you.

Join us as we explore the top sailing charters on Martha’s Vineyard that grace this picturesque island, providing you with a unique opportunity to set sail and embrace the tranquil serenity of the sea while reveling in the island’s rich maritime history and breathtaking coastal vistas.

“There is no better tool or equipment you can have on board than a well-trained crew.” —Larry Pardey

Our Pick for the Top Sailing Charters on Martha’s Vineyard

Witch of Endor Sailing Charters | Vineyard Haven Harbor | Vineyard Haven

Witch of Endor Sailing Charters, operating around Martha’s Vineyard, Massachusetts, has been sharing the joy of sailing with countless individuals and families for over two decades. They’ve become a cherished part of many Vineyard traditions, with families returning each summer to embark on their voyages. Witch of Endor has also been a choice for intimate wedding ceremonies and has performed the solemn scattering of ashes at sea, a testament to their meaningful role in people’s lives.

Witch of Endor offers various sail durations, including destination sails that allow passengers to explore different coastal towns. These one-way excursions provide a unique perspective of the island’s topography and create opportunities for convenient, picturesque arrivals at dinner reservations in another town.

Their flexibility extends to return options, such as leaving a car at the destination harbor or using the public bus system, taxis, or rideshare services. Popular destinations include Vineyard Haven to Edgartown, Vineyard Haven to Menemsha, and Vineyard Haven to Woods Hole, among others.

With a commitment to customization and a quarter-century of sailing expertise, Witch of Endor Sailing Charters invites you to craft your ideal sailing experience and be part of their enduring legacy in the Vineyard sailing community.

“A sailor is an artist whose medium is the wind. Live passionately, even if it kills you, because something is going to kill you anyway.” ―Webb Chiles

Catboat Charters | 1 Dock Street | Edgartown

Catboat Charters offers a serene and personalized sailing experience around Martha’s Vineyard and Newport, Rhode Island. With a focus on relaxation, their USCG-certified captains ensure a safe and enjoyable journey for private groups of up to six passengers. Their 30-foot catboats provide ample space to lounge in comfort, complete with a private restroom and drinking water onboard. Guests are welcome to bring their own snacks and beverages, making it a truly customized experience.

Catboat Charters believes that sailing is best enjoyed with a small group of friends or family, allowing for a more intimate and enjoyable adventure. Their two-hour private sailing charters include amenities such as blankets and a Bose Bluetooth speaker, ensuring a comfortable and memorable outing. Whether you choose to explore Martha’s Vineyard or Newport, this charter provider promises a relaxing and scenic sailing experience that’s perfect for any occasion.

“If you are going to do something, do it now. Tomorrow is too late.” —Pete Goss

Island Sailing Tours

Island Sailing Tours, a premier sailing charter provider, offers an unforgettable maritime experience around Martha’s Vineyard, MA, and beyond. Their stunning vessel, Tandemeer, a classic 60′ ocean-going ketch, provides ample space for guests to relax and enjoy the journey. With comfortable lounging areas inside and out, a classic teak interior, and an attentive crew, Island Sailing Tours ensures a luxurious and relaxing voyage.

For those embarking on overnight sails, Tandemeer boasts four private double staterooms, each equipped with ensuite facilities, plush linens, towels, and gourmet meals prepared by a talented chef.  Captain Sequoia Sun, the owner of Tandemeer and Island Sailing Tours, brings over 50 years of sailing experience to the helm. 

“Ships are the nearest things to dreams that hands have ever made, for somewhere deep in their oaken hearts the soul of a song is laid.” —Robert N. Rose

Sailing Martha’s Vineyard | Menemsha jetty dinghy dock and Basin Road | Chilmark

Sailing and Martha’s Vineyard are inseparable, and “MT-105” offers an exceptional seafaring experience. This 105′ mega-yacht is a sailor’s dream, providing idyllic island passages and breathtaking adventures. From short, protected sails around the pristine Elizabeth Islands to exhilarating ocean journeys, “MT-105” delivers it all.

Explore secluded gems like Cuttyhunk or sail to Nantucket for a night on the town. The vessel’s flexibility, combined with fair pricing and direct booking options, makes every sail memorable. With “MT-105,” the wind powers your voyage, and memories become treasures.

“How inappropriate it is to call this planet Earth, when clearly it is Sea.” —Arthur C. Clarke

Mad Max Sailing Adventures | 25 Dock St | Edgartown

Mad Max Sailing Adventures is a prominent sailing charter provider operating in the picturesque waters of Martha’s Vineyard, MA. With over 30 seasons of experience, they have garnered a loyal following of return customers who consider their sailing trips the best activity on the island. The company offers afternoon and evening sails departing from their marina on Historic Edgartown Harbor.

Their state-of-the-art Catamaran, Mad Max, is designed for both speed and passenger comfort, ensuring a smooth and stable ride. Passengers can relax in the shaded cabin or lounge on the netting up front, immersing themselves in the soothing sounds of the water.

Mad Max offers 2-hour public cruises in the afternoons and evenings, making it a convenient and exhilarating way to explore Martha’s Vineyard’s coastal beauty. For those seeking a more intimate sailing experience, visiting earlier in the week is recommended, as the tours tend to get busier as the week progresses.

“I was amazed that what I needed to survive could be carried on my back. And, most surprising of all, that I could carry it.”—Cheryl Strayed

Sail Ena Vineyard Sound Sailing Charters

Sail Ena Vineyard Sound Sailing Charters offers a quintessential sailing experience around Martha’s Vineyard, MA. Whether you seek a leisurely ride or a more firsthand adventure, Sail Ena provides options for all. Guests can relax while enjoying traditional sailing on Vineyard Sound or actively participate in raising sails and taking the tiller, feeling the excitement of sailing firsthand.

As the sun sets, Sail Ena offers enchanting sunset sails, creating the ideal conclusion to a day on the water. Moreover, they offer specialized sailing instruction for women, conducted by women instructors. These sessions provide valuable skills and confidence in a relaxed and enjoyable atmosphere, available for both groups and individuals by appointment.

“Confronting a storm is like fighting God. All the powers in the universe seem to be against you and, in an extraordinary way, your irrelevance is at the same time both humbling and exalting.” ―Francis LeGrande

Summary of Sailing Charters on Martha’s Vineyard

In the maritime paradise of Martha’s Vineyard, sailing enthusiasts are spoiled for choice when it comes to unforgettable experiences on the open water. From the tranquil beauty of Vineyard Sound to the captivating charm of the island’s coastline, there’s no shortage of breathtaking scenery to explore. Sailing charters like Sail Ena Vineyard Sound Sailing Charters epitomize the maritime magic this region has to offer. Whether you seek a leisurely sail, an educational experience, or an adventurous outing, these charter providers cater to all preferences.

Other esteemed charters, such as Catboat Charters, also ensure that Martha’s Vineyard remains a premier destination for sailing aficionados. With their seasoned crews, well-maintained vessels, and the allure of Vineyard Sound’s crystal waters, these charters promise unforgettable moments for families, couples, and solo adventurers alike.

Check out other ideas for a Day Trip to Martha’s Vineyard.