- Distance from Boston: 90 miles
- Best time: May to October
- Best for: FamilyOutdoorBeaches
Arriving into the ferry docks of Martha's Vineyard, one begins to think of presidential getaways, picture-perfect New England beaches, and of course, sharks. Not for nothing did Steven Spielberg choose this postcard vista as the backdrop for his 1975 film, Jaws, the ideal counterweight for his thriller. These days, there's nothing ominous on the resort island—at least beyond the threat of gallons of ice cream doing serious damage to your waistline. But there's plenty of biking, hiking, and other outdoor pursuits to take care of that. There's also the ever-present possibility that you'll want to cast off your mainland responsibilities and stick around for a while. It's an understandable fantasy. The Vineyard has attracted the rich, famous, and regular folk for its carefree lifestyle of flip-flops, bicycles, boats, sand, and perfect sunsets. – By Lisa Oppenheimer
Martha's Vineyard Cheat Sheet
View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View
1Start the adventure with roughly forty-five minutes aboard The Steamship Authority. With the island's most frequent service, the line offers numerous daily departures to and from Vineyard Haven and Oak Bluffs. Arrive early enough to scope out a seat if you have a preference for indoors or out and make sure to leave an extra hour for parking and traveling to the dock from the off-site lot. The Steamship is the only boat that hauls cars, but reservations are nearly impossible to score. And you're probably better off without the car anyway.
2Seafood specialties—fresh gumbo, seafood risotto, and of course, lobster—are only part of what's to love at the Blue Canoe Waterfront Grill. Grab a seat on the deck and enjoy the fresh air, the view over the harbor, and the evening breeze. Newly introduced to the formerly dry town: beer, wines, and spritzers (no hard alcohol).
3Enjoy a walk through the quaint shops of Vineyard Haven. The hamlet has a lower-key vibe than its neighbors and shutting down early thanks to its formerly dry-town status (there are still no liquor stores, but some restaurants now serve wine and beer). Those longing for harder alcoholic refreshment will need to visit either Oak Bluffs or Edgartown. If you're up for some entertainment, head to the Capawock Theater (43 Main Street; 508-627-6689) for modern films in a throwback movie experience. The tiny gem comes complete with a single screen and a loveably undependable projector that occasionally breaks down.
1Breakfast starts with a pastry and a cup of coffee from the Island staple—the Black Dog Bakery Café. Make sure to get a bottle of water or fill a reusable for the trip ahead.
2Walk across the street to Martha's Vineyard Bike Rentals. Outfitter and owner Bob will set you up with wheels, helmet, lock, and map, before directing you out onto the road. The ride out of Vineyard Haven is a little tricky, roughly three miles of travel, with traffic along Beach Road. Once in Oak Bluffs, lock the bikes and investigate the town.
3 Leaving Oak Bluffs, begin the quieter ride among the gingerbread houses, past Ocean Park toward the main bike trail. The trip along Seaview Avenue offers protection from traffic and the ability to enjoy the ocean breezes, the sound of the waves, and a leisurely six-mile or so pedal along the water.
4 Park the bike at one of the beach access points across the street from the bike path (cross carefully!) and stick your toes in the surf and sand along Joseph Sylvia State Beach.
5Pedal over the American Legion Memorial Bridge (otherwise famously known as the Jaws Bridge) and into Edgartown town center. Walk the bikes and rest near the ferry dock at Among the Flowers Café(Mayhew Lane; 508-627-3233) where breakfast—homemade pancakes, waffles, and fresh omelets—can be ordered all day long (they have lunch, too).
6 Take the five- to ten-minute walk over to the Edgartown Lighthouse where the light keeper is available daily in the summer to let you walk the stairs to the lantern room.
7Back in Edgartown, hit Mad Martha's (8 Union Street; 508-693-5883) for ice cream—you've earned it—before getting ready to make the return trip to Vineyard Haven. Too tired? Public Martha's Vinyard Transit busses run between the two towns—they can take up to two bikes at a time (no bikes allowed inside busses), but availability is hit or miss.
8 Return the bikes and clean up for dinner. Taxi to Edgartown and then enjoy a sunset water transport from Edgartown to lovely The Dunes (formerly Lure Grill). Specialties of the house include seasonal seafood and locally grown vegetables.
1The Right Fork Diner is the place for all-American breakfast staples like eggs, pancakes, French toast, corned beef hash, and the all-important home fries. Sit on the deck outside and watch the scenic biplanes take off and land on Katama Airfield—if you're brave enough, think about signing up for your own scenic flight.
2Head back to Edgartown and take a walk along the quaint shops. Look for a number of galleries sprinkled on North Water Street as well as on the outskirts of Main Street.
3The over-the-water deck at The Seafood Shanty has a boat vibe. Pretend you're at sea while enjoying your all-important fish 'n chips or fish sandwich before hopping on the ferry back to the mainland.
Where to Stay
The rooms at the Wesley Hotel (rooms from $155/night) in Oak Bluffs are admittedly on the plain side and pretty dated. But the outstanding location will appeal to those who enjoy the town's lively restaurants and night spots, and it's one of the few places in season that you might be able to score an affordable room.
Right on the main drag of quiet Vineyard Haven, the lovely Mansion House Inn and Health Club (rooms from $99/night) exudes charm from the outside in. What you see is the latest version of the hotel, rebuilt and reopened in 2003 after a fire burned it to the ground. And, for the luxury it offers, it's about the best bargain in town.
Sitting across the street from the ocean, Isabelle's Beach House (rooms from $150/night) owns some prime real estate. The eleven-room property takes advantage with a front porch sporting rocking chairs, perfect for enjoying the evening ocean breeze.
When to Go
If you think summer on the Vineyard is glorious, you're in good company. Most innkeepers and restaurant owners earn their keep between Memorial Day and Labor Day, when room rates sky rocket by the hundreds. For our money, bumper season (early May and September) are perfectly wonderful weekends. What's open when varies by location—Edgartown can be mighty quiet before the Memorial Day season.
Of course, residents live here year round, and some particularly fun events include the October food and wine festival, and the quaint Christmas in Edgartown events.
How to Get There
By Ferry: Ferries to the island run out of Falmouth (Island Queen to Edgartown), Woods Hole (Steamship Authority to Vineyard Haven and Oak Bluffs), and Hyannis (Hy-Line Ferry into Oak Bluffs). The latter is the most expensive and lengthy of the three. Steamship provides the most frequent services, operating multiple trips daily yea round. Leave yourself plenty of time for travel, as parking for Steamship is offsite and requires free bus transport to the dock that could tack on a half hour or more to the trip. It's complicated and expensive to bring a car; bikes require a nominal charge.
By Car: Depending on time of year, driving to the Ferry port can take an hour and a half to many hours down I-93 South.
By Bus: Peter Pan Bus Lines runs service from Boston to Woods Hole.
Since you won't be bringing a car to the island, you'll have to rely on alternate transportation: foot, cab, bike, moped, or bus. When biking, be wary of traffic and especially wary of sand that can wipe out a bicycle in a hurry.
Car Rental Deals
- Up to 20% Off -- Discounted Car Rentals Across the U.S. Sixt rent a car
- $33 -- Compact Crossover SUV Rentals through Fall Sixt rent a car
- Up to 15% Off -- Discounted Car Rentals Across the U.S. Sixt rent a car
- $39 & up -- Luxury Car Rentals this Fall, incl. Mercedes Sixt rent a car