The Ultimate Guide to the Summer in the Hamptons

 

The Summer in the Hamptons Handbook

Your Guide to an Effortlessly Chic and Enjoyable Season Out East

1. The Essentials

When to Go:
Memorial Day through Labor Day is peak season, but early June and September are less crowded and still gorgeous.

What to Pack:

  • Linen everything (shirts, dresses, pants)

  • Swimsuits & cover-ups

  • A great hat and sunglasses

  • A light sweater or shawl (evenings can be breezy)

  • Comfortable sandals and espadrilles

  • A beach tote and sunscreen

  • White-on-white outfits for those sunset dinners

  • Bug spray (trust us)

2. Getting There

By Car:
Plan ahead—Friday traffic can be brutal. Leave early or very late. Parking at beaches often requires a permit (check with your town or rental).

By Train (LIRR):
The Cannonball is your best bet—express from NYC to Westhampton in under 2.5 hours.

By Bus:
Hampton Jitney or Ambassador—they’re air-conditioned, have Wi-Fi, and offer snacks.

By Helicopter:
Blade, if you're feeling glamorous or avoiding Friday traffic.

3. Where to Stay

  • Rental Homes: Airbnb, VRBO, or local brokers—book early!

  • Hotels: Gurney’s (Montauk), The Roundtree (Amagansett), The Reform Club (Amagansett), Topping Rose House (Bridgehampton), and Baron’s Cove (Sag Harbor).

  • Guest Houses & Inns: For a quieter, cozy experience.

4. Beach Life

Top Beaches:

  • Main Beach (East Hampton): Iconic and family-friendly

  • Coopers Beach (Southampton): Classic with calm waters

  • Sagg Main (Sagaponack): Local favorite

  • Ditch Plains (Montauk): Surfer haven

  • Two Mile Hollow (East Hampton): Trendy crowd, big umbrellas

Beach Tips:

  • Bring your own chairs, towels, and snacks

  • Some beaches require parking permits—check ahead

  • Arrive early or after 4 PM for a quieter scene

5. Where to Eat & Drink

Breakfast & Coffee

  • Jack’s Stir Brew (Amagansett & Sag): Great organic coffee

  • Left Hand Coffee (Montauk)

  • Golden Pear Café (Multiple locations): A classic

  • Carissa’s (East Hampton): Don’t miss the olive sourdough

Lunch Favorites

  • Lunch/Lobster Roll (Amagansett): Classic roadside seafood

  • Duryea’s (Montauk): Lobster Cobb and unbeatable sunset views

  • Coche Comedor (Amagansett): Coastal Mexican

  • Pierre’s (Bridgehampton): Chic bistro vibes

Dinner Spots

  • Nick & Toni’s (East Hampton): Legendary and celeb-loved

  • The Crow’s Nest (Montauk): Dreamy and boho-chic

  • Tutto il Giorno (Sag Harbor): Elegant Italian

  • Topping Rose House (Bridgehampton): Stylish and farm-to-table

Cocktails & Sunset

  • Navy Beach (Montauk): Toes in the sand, rosé in hand

  • Sunset Beach (Shelter Island): A Euro-style party at golden hour

  • Wölffer Estate (Sagaponack): Wine tasting with vineyard views

6. Activities Beyond the Beach

  • Farm Stands: Round Swamp, Amber Waves, and Balsam Farms for the freshest local produce

  • Wölffer Estate Vineyards: Tastings, live music, and yoga in the vines

  • Shopping:

    • East Hampton: high-end boutiques and designer stores

    • Amagansett Square: local, curated, and adorable

    • Sag Harbor: charming and walkable with indie shops

  • Boating & Paddleboarding: Rent or charter in Sag Harbor or Montauk

  • Hiking: The Walking Dunes in Montauk or Elizabeth Morton Wildlife Refuge in Noyack

  • Art & Culture: Parrish Art Museum, The Church (Sag Harbor), and local galleries

7. Etiquette & Insider Tips

  • Be Kind to Locals: Remember, people live here year-round—treat them with grace.

  • Reservations Are Gold: Book dinners well in advance—OpenTable and Resy are your friends.

  • Weekdays Are the New Weekend: If you can swing it, the vibe is more relaxed and less crowded.

  • BYO Wherever Possible: Restaurants can get pricey, so pack picnics and drinks for the beach.

  • Early Mornings = Magic: The beaches and roads are quiet, and the light is dreamy.

8. Weekend Itineraries (Mini Sample)

Family-Friendly Saturday in East Hampton:

  • Breakfast at Carissa’s

  • Morning at Main Beach

  • Lunch from Round Swamp Market

  • Nap or garden time

  • Dinner at Nick & Toni’s

  • Ice cream from Scoop du Jour

Chic Adults-Only Day in Montauk:

  • Coffee at Bluestone Lane

  • Surf lesson or lounge at Ditch Plains

  • Lunch at Duryea’s

  • Sunset drinks at The Crow’s Nest

  • Late dinner at Sel Rrose

9. Emergency Info (Just in Case)

  • Southampton Hospital – (631) 726-8200

  • East Hampton Walk-In Care – (631) 324-9200

  • Pharmacies: White’s Apothecary (East Hampton, Southampton, Sag Harbor)

  • Towing/Roadside: Always have a backup plan if you’re renting a car

Final Words:

The Hamptons are about balancing elegance with ease. Whether you're in linen on a sailboat or barefoot at the farmers' market, just relax, enjoy, and savor the salt air. And always pack an extra bottle of rosé.