Planning a Private Journey to the Hamptons

The drive to the Hamptons is a New York ritual, celebrated and complained about in equal measure. Done badly, it is three or four hours of brake lights on the Long Island Expressway. Done well — leaving at the right hour, in a comfortable car, with a chauffeur who knows when to abandon the main road — it becomes the first, unhurried hour of the weekend. This guide covers the routes, the timing, the villages and the practical details that make the journey east feel effortless.

The routes: LIE, Sunrise Highway and Montauk Highway

From Manhattan, almost every journey to the South Fork begins the same way: through the Queens-Midtown Tunnel or across the RFK Bridge, then east on the Long Island Expressway (I-495). The LIE runs the length of central Long Island, and most drivers bound for the Hamptons leave it at Exit 70 in Manorville, heading south on County Road 111 to Route 27, Sunrise Highway.

Sunrise Highway is fast and divided as far as the Shinnecock Canal near Southampton. There it gives way to Montauk Highway, still Route 27, which narrows to a single lane in each direction through Water Mill, Bridgehampton and on toward East Hampton. This stretch — affectionately or otherwise known as the trade parade, for the convoys of contractors’ trucks heading east each morning — is where much of the summer delay accumulates.

• For Westhampton Beach and Quogue: leave Sunrise Highway earlier, at the exits serving those villages.
• For Southampton: stay on Sunrise Highway to its end, then follow Montauk Highway or local roads into the village.
• For Bridgehampton, Sagaponack, Sag Harbor and East Hampton: experienced chauffeurs often use the back roads north of Montauk Highway when the main road is at a standstill.
• For Amagansett and Montauk: continue on Montauk Highway through East Hampton; beyond Amagansett the road opens up across the Napeague stretch.
• For the North Fork: stay on the LIE to its end at Riverhead and continue on Route 25 or the Main Road. See our Long Island guide.

Timing: summer Fridays and how to beat them

The Hamptons season runs, broadly, from Memorial Day weekend at the end of May to Labor Day in early September. During those months, traffic follows a predictable weekly tide: east on Thursday evening and Friday, west on Sunday afternoon and Monday morning. Holiday weekends — Memorial Day, the Fourth of July and Labor Day — are the busiest of all, as is the Hampton Classic horse show in Bridgehampton at the end of August.

Outside the season, the journey is transformed. In September and October — the time many locals consider the best of the year — the roads are quiet, the ocean is still warm and the farm stands are at their peak. Montauk in late autumn, with its empty beaches and lighthouse light, is a different and wonderful place.

The villages, from west to east

The Hamptons are not one place but a string of distinct villages and hamlets along the South Fork, each with its own character.

• Westhampton Beach and Quogue — the closest to the city, with a lively Main Street and quiet, shingled lanes leading to Dune Road.
• Southampton — the oldest English settlement in New York State, with grand estates, Job’s Lane boutiques and the Parrish Art Museum in neighboring Water Mill.
• Water Mill, Bridgehampton and Sagaponack — farmland, vineyards and polo fields giving way to some of the most celebrated oceanfront homes in the country.
• Sag Harbor — a former whaling port on the bay, compact and walkable, with a strong literary history.
• East Hampton — elegant, tree-lined and historic, with Main Beach often counted among the country’s finest.
• Amagansett — relaxed and low-key, with wide beaches and a farmers’ market at its heart.
• Montauk — at the very end of the island, more surf town than society, crowned by the Montauk Point Lighthouse.

If you are visiting several villages in a day — lunch in Sag Harbor, the beach in East Hampton, dinner in Southampton — an hourly booking keeps the car with you. Our Hamptons destination guide has more on each.

Luggage, beach gear and pets

A Hamptons weekend rarely travels light. Between luggage, beach bags, a cooler, perhaps a set of golf clubs or a child’s bicycle, the boot of a sedan fills quickly. The simple rule: tell us everything you plan to bring when you request your quote.

• A sedan suits one or two guests with ordinary luggage.
• A [Luxury SUV](/fleet/luxury-suv) is the usual choice for families or guests with beach gear and several bags.
• An [Executive Sprinter](/fleet/executive-sprinter) suits larger groups traveling together, such as a house party or wedding guests.
• Pets may be accommodated on request; whether they can travel, and any conditions such as a carrier, is confirmed in your quote.
• Child seats can be requested and confirmed in advance.

The alternatives, honestly

A private car is not the only way east, and we would rather you choose well than choose us by default. We provide chauffeured road travel only; the services below are run by others.

• The Hampton Jitney — scheduled motorcoaches from Manhattan to the South Fork villages, including a premium service. Comfortable and economical, but subject to the same traffic as any car and with fixed stops.
• The Long Island Rail Road — the Montauk Branch serves Westhampton, Southampton, Bridgehampton, East Hampton, Amagansett and Montauk, often with a change at Jamaica. Immune to road traffic, though summer weekend trains can be crowded and you will need onward transport from the station.
• Seaplanes and helicopters — several operators fly from Manhattan to East Hampton and other East End landing points in well under an hour. The fastest option by far, at a significant premium and subject to weather.

Many guests combine them: a helicopter or seaplane east on a busy Friday, and a chauffeured car back on a quiet Monday with all the luggage. If you arrive by air, a car can meet you at the landing point for the final miles, or collect you from a private flight at a nearby airport — see private aviation transfers.

Coming home

The return journey deserves as much thought as the trip out. On summer Sundays, westbound traffic on Montauk Highway and the LIE builds from late morning and often stays heavy into the evening. Many regulars leave very early on Monday instead, arriving in Manhattan in time for a mid-morning meeting, or wait until late on Sunday evening. If you are heading straight to a flight, build in a generous margin and consider JFK, which is closer to Long Island than Newark.

Arranging your journey

When you request a Hamptons transfer, the most useful details are the exact address (many houses sit on private lanes with gates or codes), the number of guests, everything you plan to bring and your preferred departure window. If you are flying into the city first, a direct transfer from JFK or LaGuardia avoids Manhattan altogether.

Summer weekends book early, particularly around the holidays. When your dates are set, request a quote and the vehicle, route and timing will be confirmed in writing.