They may be tiny, but the Massachusetts islands of Nantucket and Martha’s Vineyard pack quite a punch when it comes to summer destinations. As our stores in both locations gear up for the peak season (late May to early September) and ambush of chic vacationers, we take a look at why the crowds flock to these East Coast colonies.


It’s said that Martha’s Vineyard – a New England haven of beaches, lighthouses, tennis clubs and cocktail hours – is named after a 17th-century British explorer’s daughter. It is, in fact, bereft of any actual vineyards.

At the height of summer, the Vineyard – or ‘MV’ – attracts day-trippers, countless celebrities and chic city-dwellers who escape their townhouses for the beach. Some locals say that you haven’t experienced the Vineyard until you’ve woken up in a lifeguard’s house; they of course throw the best parties.

DID YOU KNOW? Jaws was filmed here in 1975. It’s unlikely you’ll find any great whites in the water there today – real or mechanical – so jumping off the Jaws Bridge is a must.
DO SAY “I’ve been summering in the Vineyard [pronounced Vin-yud] with my family since I was old enough to sail”
DON’T SAY “This is my first trip to Martha’s – where’s Starbucks?” There are none, big chains are banned from the island so your Big Mac and Venti Vanilla Bean Chai Latte will have to wait.
WHAT TO WEAR Nautical stripes, laid-back summer cottons, denim, navy hues and beachy accessories, as well as a carefree attitude. Nip into Jack Wills and we’ll hook you up.
DIARY DATES The 2017 Vineyard Cup is a regatta taking place on 7-9 August, or the sing-along and lantern-lighting Grand Illumination Night, on August 17, is a tradition dating back around 200 years. The MV Times has a daily breakdown of what events are taking place too, from paddle board tours to the island’s buzzing art scene.
WHO YOU MIGHT SEE As well as being a political hotbed – the Obamas and the Clintons are spotted on the island annually, Jackie O had a home there for most of her life and it was the site of JFK Jr’s fatal plane crash – you might also bump into Oprah, Jake Gyllenhaal, Jennifer Lawrence and the Knowles-Carters.
WHERE TO STAY It’s all about rented pads and charming hotels on the beach – if you opt for Hob Knob, you definitely won’t forget where you’re staying. Oak Bluffs, where the ferry docks, has a carousel and gingerbread-style houses for classic MV charm.
WHAT TO DRINK Ice-cold G&Ts at the Port Hunter, a Dirty Banana at Donovan’s Reef in Oak Bluffs or craft beers at Bad Martha. Don’t drink on the beach though – it’s illegal. We found out the hard way.

FIND US AT 1 South Water Street, Edgartown, Martha’s Vineyard, MA 02539.


Advising us on all things bold, beautiful and unmissable in Nantucket is resident of 12 years and Nantucket blACKbook founder, Holly Finigan. The oracle for all Nantucket-related things, with the inside info on the best places to sip, shop and stay, you can leave the guidebook at home and come armed with this bookmarked on your iPhone.

DID YOU KNOW? Local claims to fame include the Whaleship Essex, which inspired the story of Moby Dick; the famous ‘Nantucket Red’ colour; and being named the best island in the world by National Geographic.
DO SAY The airport code, ACK, to shorten Nantucket.
DON’T SAY “I am the man from Nantucket…”
WHAT TO WEAR For Floaty dresses that cope well with wind and flats for handling the cobbles on Main Street. Guys should make a statement and pair Nantucket Reds or prints with a crisp white button-down or polo.
BEST VANTAGE POINTS Sunrise in Sconset and sunset on Madaket; Galley Beach for an Insta opp; and any of the lighthouses.
WHO YOU’LL SEE Reportedly Leonardo DiCaprio was on the island for a weekend and not one picture was taken of him. Privacy is respected.
WHERE TO STAY, EAT & DRINK Box (the best live music spot), BoHo (top place for Sunday brunch), Brewery (Cisco, famous for Whale’s Tale Pale Ale and its tour) – the blACKbook has all your other answers.

FIND US AT 11 South Water Street, Nantucket, MA 02554

Want to spend your summer in Martha’s Vineyard (or Nantucket) AND get paid to party there? Apply now to be a Jack Wills Seasonnaire – we’ll fly you out and put you up for the summer of a lifetime