It’s hard to believe that a magical retreat from everyday life is just a stone’s throw from the mainland, but once you visit Martha’s Vineyard you’ll understand why this idyllic 25-mile long island is so legendary. With its charming architecture, top-notch restaurants, secluded beaches and welcoming atmosphere, your transition to “island time” will be virtually seamless.
If you’re coming from Falmouth/Woods Hole, catch the Island Queen or Steamship Authority ferry, and arrive on Martha’s Vineyard in under 45 minutes (the Steamship Authority added the new 235-foot vessel MV Woods Hole to their ferry fleet in Summer 2016). If you’re leaving from Hyannis, the Hy-Line Cruises high-speed ferry or a 20-minute flight aboard Cape Air is the way to go.
Once on the Island, the Vineyard Transit Authority makes hopping around the island easy by bus. There’s even an app you can use for schedules and tracking. A more adventurous option is Sun ‘n’ Fun Rentals, which rents vehicles such as bikes and jeeps, so you can explore the island at your own pace (28 Lake Ave., Oak Bluffs).
Offshore Ale Company’s proximity to Oak Bluffs’ transportation hubs—it’s just steps away—makes it a great place to grab lunch when you get off the ferry. But the brewery is also known for its legendary hospitality, a rotating tap with more than nine of their own brews and its laid-back island vibe—so relaxed, in fact, that diners are encouraged to toss the shells of the restaurant’s complimentary peanuts right on the floor. (30 Kennebec Ave., Oak Bluffs)
Oak Bluffs is also home to the charming and oft-photographed gingerbread houses, a community of Gothic Revival cottages with elaborate curlicue accents and brightly colored paint. Started in the 1860s as a meeting place for Methodist retreats and revivals, visitors today can stroll by and admire the unique, whimsical homes before a visit to the small museum and surrounding shops.
A spin on the Flying Horses Carousel (15 Oak Bluffs Ave., Oak Bluffs) is a must on your Vineyard trip. Brought from Coney Island in 1884, it’s the country’s oldest platform carousel, and the last one still in operation. Try your hand at grabbing the brass ring for a free ride. Next, browse the shops that line Oak Bluffs’ Circuit Avenue. From art galleries and confectionaries to souvenirs and clothing stores, perusing the shops is a great way to spend a sunny summer afternoon.
Before you head to dinner, enjoy cocktails at Lookout Tavern. The waterfront bar and restaurant is an island favorite. We recommend the Betty’s Breeze, a refreshing blend of Deep Eddy cranberry juice, grapefruit vodka and club soda. (8 Seaview Ave., Oak Bluffs).
There’s only one restaurant on South Beach—the Dunes, at Winnetu Oceanside Resort. You can take a water taxi to get there, lounge by a fire pit, play on their life-sized chessboard and stroll the stunning grounds. There’s even an evening kids’ activity so parents can enjoy the Dunes’ delicious New American cuisine while the little ones keep busy. (31 Dunes Road, Edgartown)
Enjoy an award-winning brunch at the Lighthouse Grill at the Harbor View Hotel, where dishes like the lobster Benedict are prepared using locally sourced ingredients. The lighthouse and seaside views from their nautical Victorian dining room are unforgettable. (131 N Water St., Edgartown)
Just outside of the Lighthouse Grill, take a post-breakfast stroll around Edgartown Lighthouse, one of five lighthouses on Martha’s Vineyard. Originally constructed in 1828, it marks the entry of Edgartown Harbor and Katama Bay.
Spend the day sightseeing—saunter through Edgartown’s downtown shops (yes, that’s the original Vineyard Vines!) before heading off for a day at the beach.
The Aquinnah beaches and Gay Head lighthouse and cliffs on the west side of the island are known for their natural beauty, seclusion and serenity. An early site for whaling, the red clay cliffs are an important part of the Wampanoag culture.
And you won’t want to miss the legendary sunset at Menemsha Beach. Hop on the bicycle ferry from Aquinnah to watch the sun dip below the horizon with a glass of wine. (Trivia tip: The harbor town by the same name was the backdrop of Jaws.)
Head back to Edgartown for dinner at Newes from America, inside the Kelley House, an historic inn that dates back to 1742. Their menu of upscale British and American pub-style fare is a fitting way to end a day in the sun. (23 Kelly St., Edgartown)
Located in the heart of the Vineyard Haven Harbor Cultural District, the iconic Black Dog Tavern in Vineyard Haven has a great sea-faring backstory, and it’s a quintessential spot to eat breakfast. Our favorite is the Thank Georges Bank, a hearty egg and fish cake dish sure to get you through the morning. You can also visit their retail store if you’re in the market for Black Dog schwag, including their signature caps. (20 Beach Street Extension, Vineyard Haven)
After breakfast and before you take the ferry back to Cape Cod, be sure to visit Island Alpaca, where 19 acres are dedicated to raising a herd of 50 gentle Huacaya alpacas. Interact with these lovable animals, and learn more about them from the knowledgeable staff. The on-site gift shop even sells a variety of items made from the Alpaca shearing, a perfect keepsake from your Vineyard trip. (1 Head of the Pond Road, Vineyard Haven)