Inspiration for your own tailor-made trip
New York - Sag Harbour - Shelter Island
100% customisable for you
Your getaway to New York and the Hamptons starts today. Head to the airport, whizz through security and enjoy some down time in the airport lounge as you await the departure of your eight-hour flight to New York. A private driver will be waiting for you on arrival to whisk you away to your first accommodation: an arty hotel in Manhattan’s Kips Bay neighbourhood, where you’ll be staying for the next three nights. The rest of today is yours to spend settling into your new surroundings. You could turn to our coveted destination-specific Dossier to discover our top picks for bars and restaurants in the area, or you could simply kick back and relax, ready for two days of exploring ahead.
Welcome to New York, the soulful city of pizza and bagels, yellow cabs and subways, Times Square and Central Park, Broadway and SNL… the list goes on and on. You have the next two days to savour the spirited sights and sounds of this legendary city and we’re here to make sure it’s as much of a local’s experience as possible. At some point you’ll have the opportunity to explore East Village and Alphabet City, in southeast Manhattan, in the company of a friendly local resident. Once marred by social struggles, these neighbourhoods are now flourishing with trendy shops, stylish restaurants and independent cafes. You’ll also have the opportunity to join the local cycling renaissance that has swept across the city with rental bikes at your disposal for a day. This is a great way to discover the abundance of natural attractions in the city, including the banks of the Hudson River, the beaches of Brooklyn and the winding lanes of Central Park. We could also arrange for you to tour bohemian Bushwick and its street art scene with a local artist before trying your hand at a spot of street art yourself at a local workshop. After dark, New York has a slice of nightlife of everyone, from late-night Broadways shows and rooftop bars to comedy clubs and buzzing clubs, proving that it’s not called the ‘City That Never Sleeps’ for nothing.
Today you’ll be switching gears, swapping the bright lights of Manhattan for the seaside calm of the Hamptons. After breakfast this morning, collect your hire car and drive two hours down Long Island to Sag Harbour, a small upmarket village close to the beach. Make sure to make a stop along the way in Southampton to visit the Parish Art Museum, a fascinating place that documents the work of Long Island's artist colonies, from the impressionist William Merritt Chase to Elizabeth Peyton, via Pollock, Krasner, Lichtenstein and de Kooning. If, however, you fancy arriving in true style, our team can arrange for you to take off from the Hudson River by seaplane and touchdown in the Hamptons under an hour later. On arrival in Sag Harbour, settle in for three nights in an elegant bohemian hotel and spend the rest of today enjoying your new coastal surroundings. We recommend once again turning to our destination-specific Dossier to find a seaside bar for an aperitif before heading back to your hotel for a delicious seafood supper.
The next two days are yours to spend luxuriating in the laid-back lifestyle of the Hamptons, the Manhattanites’ favourite weekend getaway. You can stroll on Main Beach in East Hampton; rent a small, skippered boat and sail for a few hours around the coast of Montauk, a paradise for fisherman and surfers; cycle through the enchanting farms with their wind-washed cedars leading to the beach; and enjoy plenty of ultra-fresh lobster with your feet in the sand.
Today you’ll be embarking on a journey to a wonderfully remote spot in the Hamptons: the delightful Shelter Island, a true haven of peace and tranquility with over 18 square miles of wild beaches, ports and preserved natural sites. After breakfast this morning, hop back into your hire car and drive just ten minutes across North Haven to the South Ferry crossing, where you’ll drive onto a ferry for a short hop across the sea to Shelter Island. On arrival, check in for one night in a charming hotel overlooking the beach and spend the rest of your day enjoying life as a carefree islander. You can enjoy hikes in Mashamock Preserve, kayak to nearby Taylors Island, paddle in the gentle waters or simply kick back and relax on one of the many beautiful stretches of soft sand.
Sadly, the time has come to bid farewell to this splendid sliver of the East Coast and embark on the journey home. After one last delicious breakfast at the hotel and dip in the sea this morning, head back to New York City via North Fork, a 30-mile peninsula known for its beautiful vineyards. Drop off your rental car at the airport, whizz through security and escape the crowds with some down time in the airport lounge as you await the departure of your seven-hour flight back to the UK. Most flights depart in the evening, so you’ll spend your final night onboard before landing early the next day.
Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
