Things to do in Vineyard Haven, Massachusetts (MA): The Best Boat Tours & Water Sports

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.

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!

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.

Hello, I am Sequoia, captain of the 60' ketch "Tandemeer", a big beautiful ocean going sailing vessel. I have sailed over 50,000 miles over 50 years and have lots of stories to tell, some of them are also true! I love to take people sailing in beautiful locations and host guests on board for multi-day sails and charters.

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!

Join us this summer and let us sail you away on a ultimate sailing adventure aboard Sea Witch. Enjoy the picturesque views of the region’s popular coastline with lighthouses, historical homes, wonderful beaches and the colorful clay cliffs. Relax and bask in the sun listening to the wind and waves or get involved hoisting the sails and grinding the winches arrr!! Sea Witch is a luxurious 58 foot LOA Pearson Ketch and is stunningly beautiful when all four of her sails are set. Her 37 ton weight and deep draft keel provide a very smooth sail. Based in Martha's Vineyard, Ma from mid-June to mid-September offering 2, 4 or 8 hour daily charters . Celebrate your special event on Sea Witch. If it's your birthday, anniversary, surprise engagement, bachelor or bachelorette party or just a get together with friends or family. Whatever your preference, Sea Witch can offer something for everyone!! We look forward to having you all aboard!!

I make my living year round working the waters of Martha's Vineyard. I can honestly tell you no two days are ever the same. and no two sunsets, the same color in the sky. Vineyard Sound is a magical place, free of the hustle and bustle of land. The sky is bigger, the air is fresher. and the views are longer. I look forward to taking you and your family out and giving you the gift of a life long memory, as I have for many others over the years.