New York
New York is three trips and the seasons sort them out for you. The city works year round and is at its best in autumn and its cheapest in February. The Hamptons are summer, and the version worth having is the quieter east end rather than the part people picture. The Hudson Valley is autumn and winter, ninety minutes up the river, and it is the answer to the weekend question most New Yorkers get wrong.
We cover all three because they serve the same reader making the same decision: where do you go from New York, and when.
New York City
The thing that often decides a family stay in Manhattan is square footage. Rooms here are the smallest in America, and a family of four in 250 square feet will have a bad week regardless of how good the hotel is. That, not the children's programme, is what to book around. The Upper West Side is the family neighborhood, between Central Park and the Museum of Natural History, with playgrounds and grocery stores and none of the Times Square crush. Downtown, Tribeca and Battery Park City have the larger rooms and the handful of hotels with real pools.
Brooklyn is the other answer, and a genuinely different trip. More space, roughly 30 percent lower rates, and neighborhoods that feel like places people live. The cost is twenty to forty minutes on the subway each way to the things children want to see. With a four-year-old, stay in Manhattan. With an eight-year-old who finds the subway exciting, Brooklyn is better in almost every way, and Brooklyn Bridge Park solves several afternoons before you have booked a single activity.
The Hamptons
The mistake is treating the Hamptons as one place. Southampton and East Hampton are the ones people picture and the ones that get crowded. Amagansett, further east, has the good beaches, a walkable main street, and excellent food without the queues, which is why it's the village we send people to.
Indian Wells is the best family beach. Il Buco al Mare is the best dinner. The best casual meal is a lobster roll from Stuart's with wine from Amber Waves next door, eaten outside. And the sweet spot to visit is late September through October, when the summer weather lingers, the crowds thin, and the farm stands are still open.
The Hudson Valley
Ninety minutes to two and a half hours up the river, and the answer to the weekend question when the coast is cold. Wildflower Farms, an Auberge property near Gardiner, is the best hotel in the region. Troutbeck in Amenia is the historic estate with the better restaurant. Mohonk Mountain House is a Victorian castle on a lake with 40,000 acres behind it and is unlike anything else in America. The practical thing worth knowing: Amtrak's Hudson line runs along the river with stops at Beacon, Poughkeepsie, Rhinecliff and Hudson, which makes a car-free weekend possible if you pick your hotel with that in mind. Most of the good properties need a car anyway.
Autumn is the peak and it books out. Foliage weekends in mid-October are made in July, and it's one of the hardest bookings in the Northeast. Winter is the value window and genuinely lovely.
Best time to visit New York
The city: late April through June and September through early November. Autumn is the best of it. January and February are the value months, cold and grey with the museums nearly empty, which in a city where queuing is the main sport is a real advantage. Thanksgiving through New Year sees rates roughly double.
The Hamptons: late June through Labor Day is the season and it is expensive and crowded. Late September and October are better on every measure except swimming, and considerably cheaper. Winter is quiet and most of the good restaurants close.
The Hudson Valley: October for foliage, which is the peak and the hardest booking of the year. Summer is the second season. Winter is the value window and Mohonk in particular is at its best. Avoid March into early April, when the snow has gone and nothing has come up yet.
The pairing that works: the Hamptons in summer, the Hudson Valley in autumn and winter, and the city whenever. They complement each other rather than competing.
Which New York trip is right for you
Choose Manhattan if it's a first trip, you have young children, or the museums and the major sights are the point. Book on room size.
Choose Brooklyn if you've been before, your children are older, or you want more space and a trip that feels less like a checklist.
Choose the Hamptons if it's summer and you want the beach. Go to Amagansett rather than the towns everyone names, and go in September if you can.
Choose the Hudson Valley if it's autumn or winter, you want hiking and art and food, and the idea of a hotel with a fire lit sounds better than a hotel with a beach.
FAQs about travelling in New York
Should families stay in Manhattan or Brooklyn? Manhattan for a first trip with young children, since you're closer to the major attractions and take fewer trains. Brooklyn for more space, lower rates, and a repeat visit with older kids.
How big are New York hotel rooms? Small. A standard room in a good Midtown hotel is often around 250 square feet. Room size, connecting rooms and suites matter more than anything else when travelling as a family.
Which part of the Hamptons should I stay in? Amagansett, for good beaches, excellent food and a walkable main street without the East Hampton or Southampton crowds and prices. Montauk if you want more inventory and oceanfront hotels.
When is the best time to visit the Hamptons? Late September through October. Summer weather lingers, the crowds thin, and the farm stands are still open. July and August are the peak and priced accordingly.
How far is the Hudson Valley from New York City? Beacon is about ninety minutes by car or train, and Hudson and Amenia are roughly two and a half hours. Add significant time for Friday traffic in autumn.
Can you visit the Hudson Valley without a car? Some of it. Amtrak's Hudson line reaches Beacon, Poughkeepsie, Rhinecliff and Hudson, and a few hotels are walkable from the stations. Most need a car.
When is the cheapest time to visit New York City? January and February. Rates fall sharply and the museums are quiet.
Hamptons or Hudson Valley? The Hamptons in summer for the beach. The Hudson Valley in autumn and winter for foliage, hiking and food. They're different seasons rather than competing options.
