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 downtime in the airport lounge as you await the departure of your eight-hour flight to New York. You’ll likely touch down in NYC mid-afternoon, where a private driver will be waiting to whisk you away to your home for the next three night: an arty hotel in Manhattan’s Kips Bay neighbourhood.
The rest of today is yours to spend settling into your new surroundings. Turn to our coveted destination-specific Dossier to discover our favourite bars and restaurants in the area, or simply kick back and relax, ready for two days of exploring the concrete jungle.
To get you into the swing of all things NYC, we’ve arranged for you to head out with one of our friendly local guides to explore East Village and Alphabet City in southeast Manhattan. Once marred by social struggles, these neighbourhoods are now booming, with trendy shops and stylish restaurants on every corner.
The next day, explore NYC on rental bikes, discovering the lush banks of the Hudson River and the sandy beaches of Brooklyn. If you’re an art aficionado, we can also arrange for you to tour Bushwick’s bohemian street art scene with a local artist, before trying your hand at a spot of street art at a local workshop.
After dark, enjoy New York’s vibrant nightlife, whether it be a late-night Broadway show, a cocktail at a rooftop bar or a boogie in one of its buzzing clubs. 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 a delicious all-American breakfast, 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 stop in Southampton to visit the Parrish Art Museum, a fascinating place that documents the work of Long Island's artist colonies. If driving’s not your style, we can arrange for you to travel from the Hudson River by seaplane, touching down in the Hamptons less than an hour later.
Once you arrive in Sag Harbour, settle in for three nights in an elegant bohemian hotel and spend the rest of today enjoying your new coastal surroundings. If you’re looking for an aperitif, our Concierges are just a WhatsApp away, with recommendations for stylish seaside bars and savoury seafood suppers.
The next two days are yours for the taking, so spend some time soaking in the laid-back lifestyle of the Hamptons, the Manhattanites’ favourite weekend getaway. Stroll down Main Beach in East Hampton, or rent a small, skippered boat and sail for a few hours around the coast of Montauk, a paradise for fisherman and surfers. If you’re a fitness fanatic, we can arrange for you to cycle through the enchanting farms with their wind-washed cedars leading to the beach, before replenishing with plenty of ultra-fresh lobster with your feet in the sand.
Today, you’ll be journeying to a wonderfully remote spot in the Hamptons: Shelter Island. After breakfast this morning, hop back into your hire car and make your way 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. It’s a true haven of peace and tranquillity, with over 18 square miles of wild beaches, ports and preserved natural sites.
On arrival, check in for one night in a charming beach hotel and spend the rest of your day enjoying life as a carefree islander. While here, 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 stunning 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 and an early-morning dip in the sea, 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 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, ready to start ‘spreading the news’ (get it?) about your fantastic trip to friends and family at home.
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
