Experience Martha’s Vineyard Like A President, or Famous Actor

It’s no secret that Martha’s Vineyard is a favorite vacation destination for at past and present Presidents, many notable political dignitaries (both local and foreign), and countless famous actors, musicians, and artists alike. So what draws them here? Once affectionately known as “Hollywood of the East”, Martha’s Vineyard has been portrayed in many a novel and movie for its picturesque landscapes, pristine beaches, and its privacy. They say ‘what happens in Vegas, stays in Vegas’; well the same can be said for Martha’s Vineyard. If you’re traveling to Martha’s Vineyard and want to experience it like the President, or your favorite actor we have got some great tips for you.

First, rent a home “up-island”, what the locals call Chilmark, Aquinnah, and certain areas of West Tisbury; or rent a home on Chappaquiddick. These areas provide you with the sought after privacy you need. You’ll want something with a large yard, a lot of privacy, an ocean view, or even right on the water with a private beach. Explore some examples below.



Property #7754 is magnificent 5 b/r home located  right on Squibnocket Pond. Amenities include a steam room, infinity pool, hot tub, professional grade kitchen, exquisite linens, and much more.



Property #2060 is a striking contemporary home set high on a bluff in Chilmark overlooking the ocean. Amenities include sumptuous beddings, a home office, and 180 degree views throughout the home.


Before you even get to the Island you’re going to want to connect with  Deepwater Estate Services, an all-encompassing property management and concierge company, offering unparalleled care of your home and your lifestyle. They will provide you with a fully stocked kitchen, set up an evening with a private chef at your home, and anything else you may need or want during your stay.

Once you’re all settled into your posh home, you’re going to want to get out and explore. But you can’t just walk through town, or lay on the beach. You’re going to explore in style. To really see the island from a perspective many haven’t, look into a private tour of the island through Martha’s Vineyard Tour’s and Excursions. They will take you through the island in a custom tour specific to what you want to do and see.


What’s a trip to Martha’s Vineyard without a little yachting? Spend a day lounging on the deck of Sea Witch as she sails through the Vineyard Sound, or sunbathe on the bow of a yacht while the men fish from the stern.

After all that sun you’ll want to have dinner at one of the many glamorous restaurants we have here on Martha’s Vineyard. Alchemy has always been a spot to see and be seen; enjoy French fine dining surrounded by elegant decor. The Sweet Life is a favorite of  President and First Lady Barack and Michelle Obama for their date night. If you’re looking for something more laid back, the entire Obama family loves eating at Nancy’s on the Oak Bluffs Harbor.



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