Hamptons Travel Guide: Things to Do, Best Time to Visit & Itinerary

The Hamptons exists in the popular imagination as a playground for the rich and famous, a place of manicured hedges, white linen, and exorbitant real estate. While that reputation is well-earned, the reality of this slender stretch of Long Island’s South Fork is far more textured. Beneath the gloss of luxury cars and celebrity galas lies a region with deep maritime roots, where colonial windmills still turn in the breeze and the light has captivated artists like Winslow Homer and Jackson Pollock for over a century.

Stretching from the posh lanes of Southampton to the rugged bluffs of Montauk, ‘The End’ of the world, each village offers a distinct personality. You can spend your morning bargaining for fresh tomatoes at a roadside farm stand that has been family-run for generations, and your afternoon sipping rosé at a vineyard that rivals those in Provence. Whether you are chasing the surf in Montauk or chasing history in Sag Harbor, the Hamptons offers a quintessential American coastal escape that feels both timeless and aggressively modern.

A Legacy of Whalers and Artists

Long before the summer crowds arrived, the Hamptons was a collection of quiet farming and fishing communities. Sag Harbor, in particular, stands out as a former whaling capital that once rivaled New York City in international commerce. Walking its streets today, you can see the crooked colonial houses and the Old Whalers’ Church with its Egyptian Revival detail, a testament to the wealth brought home from the sea. This history provides a grounding counterweight to the modern glitz, offering visitors a chance to connect with the genuine heritage of the region.

The unique quality of light on the South Fork, often described as a golden, diffuse glow caused by the ocean surrounding the land on three sides, drew the Abstract Expressionists here in the mid-20th century. Visiting the studios of Jackson Pollock in Springs or wandering the galleries of the Parrish Art Museum isn’t just a rainy-day activity; it is an immersion into the cultural soul of the area. This artistic lineage ensures that despite the commercialization, a bohemian heart still beats beneath the surface.

The Icons You’ll Want to See

Montauk Point Lighthouse - Standing at the easternmost tip of Long Island, this 1796 beacon is a National Historic Landmark. Visitors can climb the 137 iron steps to the top for views that stretch to Rhode Island on clear days. Admission is $15 per adult, and parking is $8. It is located about 20 miles east of East Hampton.

Parrish Art Museum - Located in Water Mill, this stunning Herzog & de Meuron designed building resembles a modern barn and houses an extensive collection of works by artists from the varying artist colonies of Long Island. General admission is $16, and it is located right on Montauk Highway (Route 27).

LongHouse Reserve - A 16-acre reserve in East Hampton founded by textile designer Jack Lenor Larsen. It features manicured gardens and large-scale sculptures from artists like Yoko Ono and Buckminster Fuller. Timed tickets are required and cost $20; the reserve is generally open April through December.

Cooper’s Beach - One of the few public beaches in Southampton that offers day passes (though pricey at $50/day for parking). It is famous for its white quartz sand and the backdrop of historic mansions. It offers full amenities including chair rentals ($15) and showers.

Planning Your Visit

Getting to the Hamptons is part of the experience, for better or worse. The trade-off for this seaside paradise is the traffic on Route 27, often called the ‘Trade Parade’ on Fridays. To avoid the stress, many visitors opt for the Hampton Jitney bus service or the LIRR (Long Island Rail Road), both of which drop you in the center of the major villages. If you drive, aim to leave NYC before noon on Friday or very early Saturday morning. Once you are there, having a car is helpful for hopping between villages, though rideshare services are available but expensive.

Packing for the Hamptons requires a mix of beach casual and ’evening smart.’ The vibe is generally relaxed luxury; you will rarely need a tie, but a collared shirt or a nice summer dress is standard for dinner. Don’t forget to pack layers, even in July. The ocean breeze can drop temperatures significantly at night, making that cashmere sweater or denim jacket an essential item for bonfires on the beach or outdoor dining.

While summer brings the heat and the energy, the ‘shoulder seasons’ of June and September offer the sweet spot of warm weather without the crushing crowds. The water is warmest in September, the restaurants are easier to book, and the light hits the dunes in a way that makes it easy to see why people fall in love with this place and never want to leave.