New York’s JFK airport is the largest international hub, and it’s actually on Long Island, between the city and the Chequit – it takes just under an hour to drive from the airport to the hotel. Many major airlines also fly into LaGuardia airport (also on Long Island) and Newark airport, which is on the other side of the city.
From New York, take the Long Island Railroad from Penn Station to Greenport (the journey takes two and a half hours), then cross the street and hop on the North Ferry to Shelter Island. If you’re coming straight from JFK, all trains stop at Jamaica station, next to the airport.
If you plan on exploring Shelter Island and the Hamptons nearby, a car will come in handy. The area is well-connected to New York (a three-hour drive away), and the ferries to Shelter Island take cars as well as foot passengers. The best deals on car hire are usually at New York’s airports, rather than in the city. The Chequit has its own car park, which is free to use during your stay.
The little boat trip is part of the charm on any trip to Shelter Island. There are two crossings, each taking just a few minutes: the North Ferry from Greenport docks just down the hill from the Chequit, while the South Ferry links the other side of the island with the Hamptons. For longer-distance roadtrippers headed north to Boston and beyond, there’s the nifty Cross Sound Ferry from nearby Orient Point to New London in Connecticut, which cuts out the drive back down Long Island.
Worth getting out of bed for
The best of the beaches are: Hay Beach for sweeping views of Gardiners Bay and Bug Light Lighthouse; Shell Beach for activities including kite-surfing and paddleboarding; Crescent Beach for pink-tinged sunsets and an excuse for cocktails at Smith-approved Sunset Beach hotel. Stop by Picozzi’s bike shop and pick up a two-wheeler for a day of island-exploring; the roads are almost all yours and energy-sapping hills are mercifully few and far between. Or, ask the hotel to book you an activity nearby: golf, fishing, sailing and kayaking are some of the most popular. Mashomack Preserve nature reserve draws hikers, bumpkins and birdwatchers to its wetland trails. Check the concert schedule at the Perlman Music Program, an academy for string musicians run by renowned violinist Itzhak Perlman. The Hamptons are just over the water on Long Island; Sag Harbor, Southampton and East Hampton are the places to see and be seen.
Follow the winding road inland to Vine Street Café, a quaint cottage restaurant serving high-grade American classics made with produce straight from local farmers and fishermen. Modern trattoria 18 Bay, on North Ferry Road, is something of a Shelter Island institution. The four-course set menu changes weekly, but is always Italian-inspired, including an antipasti quartet and handmade pasta.
Down by the harbour, Marie Eiffel Market is Shelter Island’s own little piece of Paris. The breads and pastries are baked in-house, and the artisan cheese selection is the star of the gourmet-grocery show at the deli. The lobster roll is small but oh-so-perfectly formed, and the best spot to enjoy it is out the back on the over-water decking.
For DJ-sets and seaside cocktails with the hip Hamptons crowd, head to Sunset Beach hotel. Salt is a buzzy dockside bar and grill on the south side of the island; try the house beer or signature Dark ‘n’ Stormy.