Martha's Vineyard Tips


    • Charter a boat. You’re on an island, always looking out at the water, might as well get out on the ocean for sprawling majestic views. We'd personally recommend a sailing charter, such as The Black Dog Tall Ships. Take an evening cruise aboard the Alabama or send your kids off to the most incredible camp for a week to live-aboard the Shenandoah. Being aboard a 150’ ship under sail power is an unforgettable experience. For those of you looking to fish, Jen Clarke runs Captain Clarke’s Charters - one of the best on the island.
    • Have a clambake. Whether you’re on the beach with a fire or cozied up at your Martha's Vineyard abode, a clambake is the perfect way to slow down island style and celebrate time together. For the freshest seafood make your way to the Menemsha Fish Market. Find a giant pot, and invite your favorite people over.
    • Go to The Grey Barn. In seeing their unassuming farm stand you’d never believe that they make internationally awarded cheeses onsite from their own dairy herd’s milk. It’s the only Certified Organic Farm on Martha's Vineyard. They also make amazing fresh bread, grow tons of vegetables, and have their own meat for sale. Even better, stop there and pick up supplies to make the ultimate beach side cheese plate. Be sure to say hello to our friend Chelsea (the author and Martha's Vineyard expert for this section!) when you do!
    • Check out The Martha's Vineyard Film Festival and see what events they have going on. I’ve been to a handful of outdoor movies the past few years. Bethany Hamilton’s documentary was screened in Owen Park overlooking Vineyard Haven harbor. The Biggest Little Farm was screened on the coldest night last fall at the Chilmark Community Center. Lastly, I went to the Aquinnah Lighthouse to watch the documentary on what it took to move it. During the screening the lighthouse was flashing in the background. These all had speakers at them. TMVFF always puts on a good show!
    • The open market scene here is strong. Wednesdays and Saturdays are The West Tisbury Farmers Market and The Chilmark Flea Market. Thursdays and Sundays are The Artisans Fair. The First Friday of every month in the early evening Vineyard Haven Main Street shuts down to liven up for First Fridays Vineyard Haven. You can find music, food and art all on one street!
    • Go beach driving. Get a drive on pass (OSV Permit) from The Trustees and drive the south shore beach. It's stunning and the best way to bring your beach essentials with you. Just remember to put your car’s tires at 12PSI.
    • Go on a nature walk. I can’t say ‘take a hike’ because it strikes a nerve as it’s simply too flat here in my eyes to hike. However, there are a bunch of trails to access. Check out the TrailsMV App. I must also advise to go walk around Polly Hill Arboretum. It’s a stunning public garden.
    • Spend a day on Chappaquiddick. Play golf at the Royal and Ancient Chappy Links, even if you're not a golfer. I’m not, but I have a whole bunch of family and friends that are and it's a great course to spend time with them on without breaking the bank. There is no pressure to be good and it's only 9 holes. This course is a little gem. You can play in groups of any size and there is absolutely no dress code. Remember to hit Trader Fred's on the way to the Chappy Ferry for bulk golf balls & Tees.
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