10 Fun Boating Excursions on Martha’s Vinyard

10 fun boating excursions on martha’s vinyard

November 07, 2023

Martha’s Vineyard, an idyllic island just off the coast of Massachusetts, is renowned for its stunning landscapes, charming towns, and rich maritime history. While exploring the island on land is necessary, some of the most awe-inspiring experiences can be found just off its shores.

Boating excursions offer a unique perspective of Martha’s Vineyard, allowing you to discover hidden gems, view historic lighthouses, and witness breathtaking sunsets over the open water. Whether you’re an adventure enthusiast, a nature lover, or simply seeking a relaxing day on the waves, Martha’s Vineyard has a boating experience for you.

In this article, we’ll delve into ten of the most exciting and scenic boating excursions on Martha’s Vineyard. From sailing on classic schooners to kayaking through serene ponds, these adventures will leave you with unforgettable memories of this picturesque island. Get ready to embark on a maritime journey that highlights the beauty, history, and natural wonders of Martha’s Vineyard from a whole new perspective.

Island Time Charters

10 fun boating excursions on martha’s vinyard

Address: 59 Edgartown Rd
City/State/Zip Code: Edgartown, MA 02539

Island Time Charters offers a range of thrilling boating excursions around Martha’s Vineyard. Their private sunset cruises provide the perfect setting for special occasions, from bachelorette parties to proposals. You can sip on your favorite cocktails while enjoying a private sightseeing harbor cruise against the backdrop of a stunning sunset.

For adventure seekers, the Martha’s Vineyard Jaws Adventure by Boat is a must-do. Explore filming location.

ns from the iconic 1970s blockbuster, “Jaws,” with stops in Menemsha, Oak Bluffs, and Edgartown. Island Time Charters provides an immersive experience with options like guided walking tours and land excursions to the Gay Head Cliffs.

With a variety of add-ons available, you can customize your adventure to suit your preferences. Island Time Charters ensures an unforgettable experience exploring the beauty and history of Martha’s Vineyard by sea.

The Black Dog Tall Ships

10 fun boating excursions on martha’s vinyard

Address: 20 Beach Street Ext
City/State/Zip Code: Vineyard Haven, MA 02568

The Black Dog Tall Ships offer an unforgettable boating excursion in and around Martha’s Vineyard. Their flagship vessel, the Schooner Alabama, sets sail from the Black Dog Wharf on three-hour cruises, providing passengers with an authentic and immersive sailing experience. Guests can join the crew in raising the sails, steer the ship alongside the captain, or simply relax and enjoy the breathtaking scenery with a glass of wine in hand.

One exceptional experience not to be missed is the Oak Bluffs Fireworks Cruise aboard the Schooner Alabama. Passengers board in Vineyard Haven and enjoy a scenic sunset sail before anchoring near Oak Bluff’s village for an unparalleled view of the fireworks display. This family-friendly adventure promises to be a highlight of your visit to Martha’s Vineyard, offering an intimate connection to the island’s maritime beauty.

Sea Witch Sailing Charters

10 fun boating excursions on martha’s vinyard

Address: 350 Beach Rd
City/State/Zip Code: Vineyard Have, MA 02568

Sea Witch Sailing Charters offers an unforgettable adventure amidst the beauty and history of Martha’s Vineyard, The Elizabeth Islands, and Cape Cod. From June to mid-September, experience the thrill of sailing aboard the Sea Witch and immerse yourself in picturesque views of lighthouses, historic homes, stunning beaches, and colorful clay cliffs. Whether you seek relaxation or more active pursuits like fishing and swimming, Sea Witch provides 2 to 8-hour excursions tailored to your preferences. With U.S. Coast Guard compliance, they accommodate up to 12 guests for a memorable sailing escapade. It’s time to hoist the colors and set sail with Sea Witch!

Martha’s Vineyard Day Sails:

2-hour Harbor Sail: Explore Vineyard Haven Harbor and charming homes of East and West Chop during this introductory sailing experience. Enjoy a glass of wine or learn the basics of sailing terminology. Sunset sails are available too!

4-hour Day Sail: Venture beyond the inner harbor to soak in more breathtaking scenery and consider a one-way destination sail. Opt for catered menus or bring your own picnic while taking in the coastline.

8-hour Day Sail: Embark on a destination sail to places like Edgartown, the Elizabeth Islands, or Menemsha. Dive into scenic coves for a refreshing swim or hike to Naushon Island’s lighthouse. Full catering options are offered on full-day sails.

Join Sea Witch Sailing Charters for a maritime adventure like no other.

Pirate Adventures Martha’s Vineyard

10 fun boating excursions on martha’s vinyard

Address: 12 Circuit Ave Ex
City/State/Zip Code: Oak Bluffs, MA 02557

Prepare for an unforgettable family-friendly adventure aboard The Sea Gypsy, Martha’s Vineyard’s first and only pirate ship. Kids are transformed into hearty pirate crew members, complete with face paint, pirate names, and the chance to fire water cannons at attacking pirates. This immersive 90-minute experience combines storytelling, treasure hunting, and pirate grog for a memorable voyage.

Pirate Adventures Martha’s Vineyard offers an interactive pirate experience like no other. With safety as a top priority, their US Coast Guard licensed captain ensures a secure journey. Perfect for kids aged 3-10, this adventure leaves lasting memories of a fun-filled day at sea, making it a must-do activity for families visiting Martha’s Vineyard. Additionally, their sunset cruises and private pirate adventures offer unique ways to enjoy the island’s waters.

Plan Sea Adventure Charters

10 fun boating excursions on martha’s vinyard

Address: 53 Dock St
City/State/Zip Code: Edgartown, MA 02539

Plan Sea Adventure Charters offers an array of exciting boating excursions in and around Martha’s Vineyard. One standout experience is their Sunset Cruise, a two-hour journey around Martha’s Vineyard or Wood’s Hole Cape Cod. Guests can bring their own food and cocktails, making it perfect for special events or group gatherings. The knowledgeable local guide shares insights about the surroundings as you cruise past beautiful residences, yachts, and natural vistas.

Plan Sea’s private daytime charter cruises accommodate up to 18 passengers and provide opportunities for sightseeing, swimming, and exploring various destinations. They also offer private Cape Cod to Vineyard Party Ferries and Cuttyhunk Elizabeth Islands Private Adventure Charters, allowing visitors to discover hidden gems rarely seen by tourists. With a focus on customer service and experienced US Coast Guard licensed Captains, Plan Sea Adventure Charters promises an unforgettable boating experience in this beautiful region.

Sail Ena

10 fun boating excursions on martha’s vinyard

Address: Lake Street Landing Tashmoo
City/State/Zip Code: Vineyard Haven, MA 02568

Sail Ena offers an unforgettable boating experience on Martha’s Vineyard, operating both day and sunset sails on the picturesque Martha’s Vineyard Sound. Ena, a 34′ classic wooden sloop designed by John Alden, provides a timeless and intimate sailing adventure. Guests can relax and enjoy the serene voyage or actively participate in raising sails and steering the vessel. Departing from the tranquil Tashmoo area near Vineyard Haven, passengers are treated to breathtaking views of the North Shore and Elizabeth Islands. Private charters are available, allowing customization and the option for a refreshing swim off the boat. An utterly charming way to explore the island’s waters.

Witch of Endor Sailing Charters

10 fun boating excursions on martha’s vinyard

Address: Vineyard Haven Harbor
City/State/Zip Code: Vineyard Have, MA 02568

Witch of Endor Sailing Charters has been a beloved fixture in Martha’s Vineyard for 25 years, offering unforgettable boating excursions. Families return each summer, making it a cherished tradition, while local businesses choose Witch of Endor for their annual staff parties. Couples have gotten married aboard in intimate ceremonies, and the crew has respectfully scattered ashes at sea. They’ve generously donated charters to support causes like the Possible Dreams Auction and The Children’s Trust. With trips of three hours or more, you can sail, anchor for a swim, or explore coastal scenery. Customizable one-way excursions, like Vineyard Haven to Edgartown, offer unique and scenic adventures.

Mad Max Sailing Adventures

10 fun boating excursions on martha’s vinyard

Address: 25 Dock St
City/State/Zip Code: Edgartown, MA 02539

Mad Max Sailing Adventures offers an exhilarating boating excursion around Martha’s Vineyard. Celebrating its 30th season, it’s known as one of the best activities on the island. Departing from Historic Edgartown Harbor in the afternoon and evening, Mad Max is a state-of-the-art Catamaran designed for speed, passenger comfort, and safety. Whether you prefer relaxing in the shaded cabin or lounging on the netting up front, the twin hulls ensure a smooth, stable ride. They offer 2-hour public cruises as well as private charters for special occasions. You can even bring your own refreshments, including alcoholic beverages, and food.

Martha’s Vineyard Leisure Charters

10 fun boating excursions on martha’s vinyard

Address: Beach Road
City/State/Zip Code: Tisbury, MA 02568

Martha’s Vineyard Leisure Charters offers an array of captivating boating excursions around Martha’s Vineyard. With various options, from the Mini Insta Cruise to half-day trips to picturesque spots like Lagoon Pond and Tarpaulin Cove, they cater to diverse preferences. Their customizable trips provide many opportunities for relaxation, exploration, and even naturism experiences. With a focus on privacy, professionalism, and local island-sourced refreshments, they ensure an unforgettable time amidst the natural beauty of Martha’s Vineyard’s coastal waters, making them a top choice for sightseeing and leisurely boating adventures.

Let’s Wrap this Up!

From shark, dolphins and whale encounters to sunset sails, Martha’s Vineyard boasts a diverse range of boating excursions that cater to every type of adventurer. Whether you’re exploring hidden coves, enjoying a leisurely cruise, or seeking thrilling encounters with marine life, these top ten tours provide an opportunity to experience the island’s coastal treasures from a unique perspective. Get ready to set sail and create lasting memories on Martha’s Vineyard’s captivating waters.

Also explore – 15 Really Great Boating Excursions on Cape Cod

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