The 10 Best Boat Tours & Water Sports in Martha's Vineyard, Massachusetts (MA)

COVID ALERT: WE ARE ONLY TAKING PRIVATE CHARTER RESERVATIONS ON OUR WEBSITE The boat "Plan Sea" is a newly remodeled down east luxury yacht. She seats 18 passengers on teak-trimmed, Sunbrella-cushioned furniture. The open deck and wet bar make Plan Sea the perfect party venue. You may rent (private charter) the entire boat(offered on our website). Public scheduled cruises are DISCONTINUED due to the pandemic. Activities include tours, transportation and parties. Cruises depart from Falmouth on Cape Cod and Martha's Vineyard. Sunset cruises are a great cocktail hour cruise out of Edgartown and Falmouth. Plan Sea boat cruises are a great activity for bridal parties, women's weekends, family reunions, couples and other groups to enjoy time on the water and learn about the history and sights around the Cape and Islands. We are a proud recipient of the TripAdvisor Certificate of Excellence. Cruises fill up fast during our short season, so book now.

Sailing from Lake Street Landing, Tashmoo, Vineyard Haven by reservation only. ENA is a classic 34' Alden design wooden yacht. Take the helm and be part of the crew or sit back and enjoy the sail. Catering available on request, or bring your lunch. BYOB. Day, sunset, or full day sails. All inquiries welcome.

Ahoy mateys! Join us as we set sail on a pirate's treasure hunt along the shores of beautiful and historic Oak Bluffs on the legendary island of Martha's Vineyard. On our custom pirate ship your kids will dress and talk like a pirate, assemble a treasure map, battle rival pirates with water cannons and hoist sunken treasure from the ocean floor! Once aboard the Sea Gypsy, we must work together to build a treasure map and determine our course. Along the way, we find a message in a bottle and discover that Stinky Pete, the Island’s smelliest pirate, has stolen the keys! We must raise the battle flag, fight off our enemy with water cannons, and steal back the keys to claim our treasure! The voyage culminates as we discover where "X" marks the spot...we must work as a team (heave-ho!) to raise the treasure chest from the ocean as it's heavy with sea water and sparkling booty. Every one of the crew will be rewarded for their efforts and take home their fair share of the loot. There’s singin’, dancin’, and drinkin’ of pirate grog as we sail back to port victorious in our spoils. You’ll be amazed how quickly the Pirate Adventures crew taps into the wonder of your child’s imagination. This wholesome, family-oriented cruise is perfect thing to do on a day trip, vacation, weekend or really just about anytime your are seeking a child-friendly and action-packed bunch of fun while on MV. There is a reason why Pirate Adventures is ranked high on a family’s vacation highlights. This isn’t a performance by actors - this is a highly interactive pirate experience where each of our trained crew makes sure your child is involved and engaged throughout the whole journey. It's a fun, unique, memory-making adventure cruise designed for families by a family (a pirate family of course).

Private Sailing Charters in Edgartown on Martha's Vineyard aboard a traditional Cape Cod catboat.

DREAM CATCER is a 41ft catamarn that offers a smooth sailing experience for up to 12 passengers! All of our private charters start at $125 per person for the three hours tour! Non-alcholic beverages and light snacks provided; BYOB. You can bring your own refreshments or catering is available upon request. Celebrate any occasion and see the island from a different perspective! A vacation highlight for birthdays, family reuions, bachelorette parties, anniversaries, a way to entertain your guests or share a special memory with your friends and family. Continental breakfast cruises, midday anchor drop for lunch and swimming fun. Ask about full day destination excursions. The bow and cockpit are very spacious, plus main salon offers protection from the elements! Come sailing with out heeling...steady as she goes!

Tour the Cottage City Oyster Farm! Cottage city oysters come from the cold, clean, crisp flowing waters of the vineyard sound, oak bluffs Martha's Vineyard.

The only Ocean sports company on Martha's Vineyard! We provide Parasailing, jet ski rentals, waterskiing, wakeboarding, tubing, kneeboarding, flyboard lessons, banana boating, tubing, and boat rentals. Come have a day on the water with us!

Skylark is the perfect boat for family fun in the waters of Vineyard Sound. Fishermen ranging from beginners to old timers will enjoy catching scup, fluke and sea bass from the comfort of our 50' boat. Bait and tackle are provided. Experienced crew members help ensure that all aboard have a safe, successful and fun filled adventure. Daily trips 8am-noon subject to weather. Reservations suggested.

Wind's Up is Martha's Vineyard's premier destination for kayaking, paddleboarding, sailing and windsurfing rentals, lessons and equipment sales. Family owned and operated since 1962, our friendly and knowledgeable staff will help make your water play experience just perfect. Hourly rentals and lessons are conducted on beautiful Lagoon Pond in Vineyard Haven. All island delivery for 3 day rentals.

Experience Martha's Vineyard sailing aboard our sleek, fast, classic sailboat with Master Mariner & ASA-Certified Sailing Instructor, Captain Wendy. Exploring the beauty & history of the area by sea is the perfect adventure for your Vineyard vacation. The picturesque coastline of lighthouses, historic homes, and beautiful beaches are just a few of the beloved sights of the area. Sail aboard M.S. Resolute with us!