Discover the allure of Martha’s Vineyard, a world unto itself situated seven miles offshore and renowned for its hundred square miles of wild beauty, stunning coastline, and a cultural richness that far exceeds its celebrity reputation. From spectacular beaches and breathtaking seaside cliffs to harbor villages and waterfront hotels, there’s truly something for everyone on New England’s very own island paradise affectionately known as “The Vineyard”.
Sometimes a short getaway by air or sea is all it takes to be reminded that life is about the journey – and in this case, also the destination. Set sail on a ferry ride from Falmouth to Oak Bluffs aboard the Island Queen or Steamship Authority, or aboard Hy--Line Cruises from Hyannis Harbor, all with room to wheel your bike on deck. Or take to the skies on Cape Air for a quick jaunt from the Boston hub or downtown Hyannis.
Once you arrive on Martha’s Vineyard, you’ll find plenty of ways to get around the island from the main port towns, which will mesmerize at first sight with their variety of quaint storefronts, restaurants, and lively harbor scenes. The Vineyard Transit Authority offers island-wide public transportation and a seasonal hop-on, hop-off bus itinerary. Rent a bike or moped to see the far reaches of the island, or step aboard a vintage trolley sightseeing tour.
Known as the liveliest of the Vineyard’s bustling “Down-Island” towns, Oak Bluffs is home to historic attractions and landmarks all within walking distance of the ferry dock. Take a leisurely stroll past the kaleidoscope of colorful Victorian Gingerbread Cottages at Oak Bluffs Campground, famed for their fairytale-like architecture and storied history. Next up is The Flying Horses Carousel, the nation’s oldest operating platform carousel where you can take your favorite horse for a spin and try to catch the brass ring for bragging rights and a free ride. Children and adults alike will long remember a special visit to the Island Alpaca, spent with a herd of gentle, friendly creatures on the 19-acre farm.
When hunger strikes, have a bite atop a bluff overlooking the Nantucket Sound at The Lookout Tavern, or at the famous Black Dog Tavern in Vineyard Haven for a presidential breakfast and souvenir Black Dog merch.
Cross the legendary “Jaws Bridge” connecting Edgartown and Oak Bluffs for a glimpse into Jaws culture on Martha’s Vineyard – a popular bucket list item – then spend a relaxing afternoon strolling around Edgartown, a former whaling port steeped in maritime history, and one of the Island’s first towns. Meander through the historic streets lined with wealthy ship captains’ mansions, where you can observe Greek revival architecture and original widow’s walks while you contemplate the life in the 19th century.
If time allows, take the short “On Time” Chappy ferry to leave the crowds behind and explore the serene, Japanese-style Mytoi Gardens in Chappaquiddick. Return to the elegant Edgartown Harbor to sip, shop, and repeat at the upscale, breezy boutiques and view some of the world’s most beautiful yachts and sailboats. Visit the Island-inspired Vineyard Vines store before you wrap up the day, then take a seat at The Seafood Shanty for cocktails and a standout meal with a view.
Plan on a short journey to the Vineyard’s western tip to stunning Aquinnah for a must-see stop at the towering, jewel-toned Gay Head Cliffs, a breathtaking National Landmark and home to the Vineyard’s first lighthouse, a celebrated artifact and beacon to Native American tribal heritage. Pay a visit to Hatmarcha Gifts, a Wampanoag owned family business with an expansive collection of hand-crafted wampum jewelry, scrimshaw, turquoise and silver. Soak up the majestic landscape from the sandy shores of Moshup Beach, where you can swim, sunbathe, or simply enjoy a meditative walk on one of the Island’s most captivating western-edge beaches.
Whether you’re traveling with family, friends, or as a couple, Martha’s Vineyard offers overnight guests a multitude of accommodations reflective of the island’s charm and history. The Lark Hotels’ Edgartown Collection boasts a luxe fivesome of boutique hotels located in the heart of downtown Edgartown known for their uniquely themed coastal havens and small-plates, homemade breakfast. Among them are The Richard., The Christopher and The Edgartown Inn.
A couple miles south, you can get away from it all at Winnetu Oceanside Resort, where farm meets sea in Edgartown’s quiet Katama, just steps from South Beach. A gamut of on-site activities, weekly clambakes, water taxi, kid’s club, and popular Dunes restaurant with a calendar full of culinary events draw visitors year after year.
Book a room at Summercamp in Oak Bluffs overlooking the harbor for a playful, camp-inspired experience that will invite you to be a kid again with whimsical, nostalgic touches throughout the property. Cozy-chic rooms with all the amenities, an open-air lobby, and retro canteen and game room promise a cheerful stay.
End at least one of your days on Martha’s Vineyard at Menemsha Beach, to witness the Island’s most stunning sunset, an iconic spot to enjoy an evening picnic as the sun sinks into the horizon across the Vineyard Sound.
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