How To Live The Presidential Life on The Vineyard

PHOTO: The Mansion House in Vineyard Haven traces its history back to 1791. (Courtesy of The Mansion House)

If you don’t watch Colbert, or miss every other major website and newspaper top headlines, you might not have heard:  President Obama is going on vacation in August to Martha’s Vineyard. The Commander in Chief has taken his family there every year of his presidency but one.  So, obviously we need to go, too!  Here is the How-to Guide on Being All Presidential-like on Martha’s Vineyard.

The Low-down

Here is the skinny on the island:  It’s 100 square miles off the coast of Cape Cod, Massachusetts, it is the largest island on the East Coast not connected by bridge or tunnel to the mainland, and the main season for tourism is May through October.

Arrive in Style

The First Family normally comes in on Marine One, the official helicopter of the President.  If you want to take a car and don’t want to rent it when you get there, you will be waiting in line for the ferry like the rest of us.  Don’t feel you need to bring the car? Mopeds and bikes can get you around locally and the island has many taxis and reliable public transportation. 

You can fly to the island if you would like.  Flights are a little pricey and typically come through Providence (that is, assuming you don’t have your own official helicopter).

Living it up

The Prez is staying in the Town of Chillmark in a secluded, $12 Million, 17-room house that overlooks the North Shore. If you want to be boss like the country’s boss, you should saddle up in a place, too.  There are over 100 house for rent at the rate of $20,000-$50,000 per week should you feel excessive. 

There are many fine houses available to rent as low as $800 a week.  If you go through www.vrbo.com you can get the price down below $700 a week.  Most home are pet-friendly, too. If a hotel is more your thing, there are 13 on the island.  I love the style of the Mansion House in Vineyard Haven, and rates start about $309 a night.

Eat like a King

President Obama always makes his way to Nancy’s restaurant.  They do two different styles of food at Nancy’s.  Downstairs, at the snack bar, you can take away fried fish and seafood, sandwiches, salads, or a list of Middle Eastern Dishes.  Upstairs, they have a full sit down lunch and dinner menu including a full raw bar.

I recommend Nancy’s Clambake, a full-out feast for two of New England clam chowder, lobster, steamers (clams), mussels, sausage, corn on the cob and potatoes.  I bet you can’t finish. 

If you are looking for something else besides shellfish, head over to Black Sheep and Trio, a cheese shop by day and restaurant by night.  They offer up fresh cheese and charcuteries with wine pairings and desserts.  A great place for as they put it, “before dinner, after dinner, before a movie, after a movie ... for dinner ... for drinks ... for a great experience.” 

Don’t miss the island’s only brewery, the Offshore Ale House.  They brew beer and serve up traditional pub fare and seafood favorites.

 Hold Court

The Obamas frequently ride bikes and head to the beach on the island, and the President golfs quite a bit.  Biking, moped riding, charter fishing, and horseback riding are the most popular activities.  The shopping, dining and art galleries are fantastic as well. 

The waves at South Beach are considerably bigger because they are on the ocean side, so if you like to body surf / boogie board this is the place for you.  If you do get some bad weather during your stay, seek out the indy / classic films at the Martha’s Vineyard Film Center.  They won’t let you down.

The Gayhead Light, an active aid to navigation, is a lighthouse with one of the best views on the island.  If you have ever seen Black Dog brand clothing, it originated on Martha’s Vineyard.  They have a store as well as a tavern in Vineyard Haven. 

If you want to be like a Kennedy and head to Chappaquiddick, make sure you take the Trustees of the Reservation Tour and find out there is much more to the island than just the infamous Dike Bridge.

There is one “must-do” activity in Martha’s Vineyard:  The Flying Horses Carousel.  Designated as the nation’s oldest platform carousel, it still has a traditional ring assembly, where you can still grab at the rings hoping for one of brass.  I am very proud to say, that is the only place I ever grabbed a brass ring (unless my wife asks, in which case when I found her I grabbed one as well).

I know your mother always told you, “You can be anything when you grow up, even President of the United States.” Well at least at Martha’s Vineyard you can summer just like one.