Where the President Plays: A Martha's Vineyard Guide for the Rest of Us

A Quick Guide to the Massachusetts Island of Martha's Vineyard

Obama Martha's Vineyard Souvenirs
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Like the Clintons before them, the Obama family has repeatedly selected Martha's Vineyard as their summer vacation destination. President Obama, his wife Michelle and daughters Sasha and Malia vacationed on Martha's Vineyard at the secluded Blue Heron Farm in August of 2009, 2010 and 2011, and since 2013, they have rented private homes in Chilmark for their vacations. In 2016, the First Family is back in Chilmark for a two-week stay August 6 through 21.

See Photos from the Obamas' 2013 Stay and First Vacation on Martha's Vineyard

Planning your Martha's Vineyard escape should not be nearly as complicated: I can't imagine it is an easy trick coordinating accommodations for the president and his Secret Service entourage. Reports say his 2016 island motorcade was 25 vehicles long. 

A variety of Internet resources can make your Martha's Vineyard vacation planning easy.

Getting There

Martha's Vineyard is located seven miles off the coast of Cape Cod and is accessible via ferry. Find your island ferry transportation with my guide to ferries serving Martha's Vineyard, Cape Cod and Nantucket.

The Steamship Authority's ferry from Woods Hole to Martha's Vineyard makes several trips daily and operates year-round. The Ferry's Web site provides schedule and fare information, as well as directions to the departure point.

The Steamship Authority provides the only car transport to Martha's Vineyard, and in the summer, a vehicle reservation is a must. Reservations are a good idea during non-peak travel times, too, if you want to be absolutely certain that your car or other vehicle can make the trip with you.

If you're planning a visit of three days or less, my recommendation would be to leave your car behind. You'll find a number of other transportation options once you arrive on Martha's Vineyard including public shuttle buses, taxis and rental cars, mopeds and bicycles.

Need a rental car on Martha's Vineyard? Compare rental car prices with Expedia.

Martha's Vineyard can also be reached by air. Cape Air offers flights to the island from Boston, New Bedford, Nantucket and Hyannis, Massachusetts; White Plains, New York; and Providence, Rhode Island.

If you wish to reach the island via your own boat, contact the harbormaster in Edgartown, 508-627-4746; Menemsha, 508-645-2846; Oak Bluffs, 508-693-4355; or Vineyard Haven, 508-696-4249.

Where to Stay

You'll find a plethora of accommodations options on Martha's Vineyard, ranging from private homes available for rent to quaint bed & breakfast inns to classic hotels. Here's a collection of helpful resources for finding lodgings on Martha's Vineyard.

Click Up a Martha's Vineyard Vacation - The Winnetu Oceanside Resort makes it easy to escape to Martha's Vineyard. Here's my review of this all-suite resort.

Bed & Breakfasts on Martha's Vineyard - Find a bed & breakfast inn on the island of Martha's Vineyard in Massachusetts with my B&B guide.

Martha's Vineyard Vacation Rentals - You'll find listings for several Martha's Vineyard rental homes and cottages, plus real estate agents that specialize in Martha's Vineyard rentals, among my links to Massachusetts Vacation Rental Resources.

Martha's Vineyard Camping - Although options are limited, camping is a possibility for those seeking an affordable overnight on Martha's Vineyard.

Vacation Rentals by Owner - This rental listing site has dozens of current properties for rent on Martha's Vineyard, ranging from a six-bedroom waterview home with a heated pool to a quaint two-bedroom cottage on a quiet lane in Edgartown.

Martha's Vineyard Resort - This island resort offers so much for sports lovers! A private sundeck overlooks two championship clay tennis courts. Golf, fishing, sailing and hiking are all nearby, as are Martha's Vineyard's quaint shops, historic landmarks, art galleries, beaches and restaurants.

Call the Martha's Vineyard Chamber of Commerce at 508-693-0085 for more lodging suggestions.

Next Page: Island Dining, What To Do, More

Martha's Vineyard Island Dining

Unlike Barack Obama, you probably won't have your own chef while you're vacationing (although the Huffington Post reported that the first couple had a date night at the Beach Plum Inn in 2011, and they returned to this romantic island favorite in 2013, according to the Daily News. And State Road is another of the Obamas' favorite Martha's Vineyard restaurants).

Here are more dining ideas on Martha's Vineyard:

The Beach Plum Restaurant - Consistently ranked one of the best restaurants on Martha's Vineyard and the choice of the presidential pair, the Beach Plum in Menemsha offers panoramic views and regional cuisine.

Down Island - This Oak Bluffs newcomer welcomed President and First Lady Obama for dinner in 2016. The menu is ever-evolving at this prix-fixe, come-as-you-are, communal restaurant.

Larsen's Fish Market - In the fishing village of Menemsha, Larsen's is a destination for fresh-caught seafood cooked to order, or pick up fresh fish and prepare a memorable meal at your rental accommodations.

The Outermost Inn - This restaurant perched high upon the island's Gay Head cliffs boasts of its spectacular sunsets and offers scenic dinner views as well as overnight bed and breakfast accommodations.

The Martha's Vineyard Online Dining Guide has plenty of other suggestions: This online database of Martha's Vineyard restaurants is searchable by restaurant category or location. The Martha's Vineyard Chamber of Commerce also offers a Restaurant Guide online.

What to Do on Martha's Vineyard

Martha's Vineyard is known for its beaches, 19 of them in all! If fishing is your thing, Martha's Vineyard Online has listings for Martha's Vineyard Fishing Charters. Or, why not explore the island on a bike like the Obamas have? TravelMuse offers advice on Biking Martha's Vineyard and several suggested routes.

Avid golfers can choose from two public golf courses on island: Farm Neck Golf Club in Oak Bluffs or Mink Meadows Golf Club in Vineyard Haven.

Art galleries abound on Martha's Vineyard. Here are a few you might visit: The Granary Gallery in West Tisbury represents dozens of island artisans in just about every medium; Seastone Papers, also in West Tisbury, specializes in handmade papers; and the Field Gallery in West Tisbury represents contemporary works by island artists.

You'll also want to see: The Flying Horses Carousel, the oldest operating platform carousel in the U.S. and a National Historic Landmark; the gingerbread cottages of the Martha's Vineyard Camp Meeting Association in Oak Bluffs; the island's oldest residence, Vincent House, which is open for tours Monday through Friday in season; and one or all of the five lighthouses on the Vineyard.

More Martha's Vineyard

Other interesting reading:

Martha's Vineyard History - This account of the island's origins and history was written in 1923 by Henry Franklin Norton.

Previous Page: Getting to the Island and Martha's Vineyard Lodging Options