Live Like A Blueblood: Your Guide To New England’s Best Islands


Most of the year, the Eastern Seaboard of the United States is pounded by the most dour of weather, be they Nor’easters, chilly damp air, and/or blankets of fog with the consistency of pea soup. Once the peak summer months roll around though, this miserable pattern of weather breaks up, leaving behind bright sunny skies to reign over a spectacular seascape of rocks, hardy coastal forest, and windswept fields of grass upon the many islets that dot the coast off of mainland New England.

This ideal mix of ocean-moderated summer warmth and seclusion from the urban madness of centres like Boston and New York City have made these islands popular with multiple generations of America’s power elite, or the so-called “old money” classes that built America’s business, cultural, and political institutions. While you may never quite possess the power and influence that they wield (and continue to do so in the present day), it is fun to pretend for a few days while you do some escaping of your own from the responsibilities of the world.

While you could spend much of the rest of your life exploring every isle from Connecticut to Maine, here are three essential islands in New England where you can live the blueblood life, starting with…

1) Martha’s Vineyard, Massachusetts

While Martha’s Vineyard has been a favourite haunt of the Kennedy clan and former president Bill Clinton (who reportedly still vacations here from time to time) in the past, in this day and age, it has also proven to be quite popular with many Hollywood A-listers as well, so keep those binoculars handy.

Also keep your charm working at a high level while you are here, as many wealthy people keep a low profile. So if you strike up a friendly conversation at the beach or in a local pub, you might find yourself with an offer to golf on a guest pass at a private golf club like the Vineyard, where President Obama golfs periodically, and memberships cost $300,000 … if you can successfully apply for a vacancy that is.

2) Nantucket, Massachusetts

While this island’s name may be associated with a rather rude limerick, it is also another enclave of the top 1% in the Boston area, be they lawyers, surgeons, CEO’s or tech millionaires. The true attraction of this place is its outstanding nature, so when you go walking along its wild beaches, through its wetlands, or on its historic and well-preserved old town centre, you are living a life of the local elite, as they have contributed their money and clout to protect this place from the ravages of over-development.

If that isn’t enough for you, then stroll down its main shopping street, and window-shop/splurge at boutiques such as Ralph Lauren, The Golden Basket, or Shreve, Crump & Low, which are all places where you can daydream or pretend to be one of Nantucket’s super affluent locals.

3) Block Island, Rhode Island

If you’re seeking out a place with a more lively party vibe, but you still want to retain a touch of class, then Block Island is an ideal choice. Start by booking a room at the National Hotel, an old stately manor listed on the National Register of Historic Places, and make reservations for dinner at the Atlantic Inn Restaurant, a favourite dining place for celebrities, as it serves four sumptuous courses under romantic candlelight.

Take up windsurfing lessons on the beach during your stay, and you’ll be taking up one of the favourite watersports of bluebloods over the years, and if you’re lucky, you might meet a few in the process!

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