Luxury insider tips on the best first trip to East Hampton

Our Insider Itinerary series shines a light on the best places to see, stay, and dine in some of the hottest travel destinations worldwide. Our far-flung correspondents are sharing their inside tips on how to best experience their chosen locations, especially if you’re visiting for the first time. Consider it your local luxury GPS. You’re welcome! In this edition, we head to East Hampton, New York. What are the best places to see, stay, and eat out in East Hampton? We’ve got insider tips on restaurants, activities and hotels for a trip to East Hampton.

the insider itinerary

The best way to ensure that your precious vacation time is well-spent is to ask a trusted insider about what’s truly special at your destination of choice.

Just in case you don’t have such a person in your network, dear reader, we’ve done the work for you.

Our far-flung correspondents have shared their insider tips on the ideal itinerary for a first trip to Cape Town, South Africa; Copenhagen, Denmark; and the island of Nantucket, Massachusetts.

Next up? Another gorgeous summer destination: the village of East Hampton, New York.

We’ve visited the Hamptons many times, but we wanted the deep inside scoop from someone who owns a home and has a real history in East Hampton. So we turned to one of our friends, who prefers to remain anonymous (so he could speak frankly), to fill us in.

Luxury insider tips on the best first trip to East Hampton

Here’s what our East Hampton Bureau Chief had to say about the iconic summer spot:

1. How long have you had a summer home in East Hampton?

Since I was born, so 50 years.  My grandparents had a weekend home in East Hampton. My wife and I have had our current home in East Hampton village for six years.

2. Why did you choose East Hampton over other towns and villages in the Hamptons? What drew you there?

The natural beauty was the key factor.  It’s also a history buff’s dream.

3. If someone is visiting there for the first time, what are the top 3-5 “must see” sites, or experiences, or activities? 

Camp Hero State Park in Montauk is a special place for exploration and for family picnics.

Camp Hero State Park

Main Beach is fun for kids and adults alike.

Main Beach, East Hampton, New York

Guild Hall is a gem for those into the Arts, with well-curated film screenings, plays and special musical acts.

Guild Hall, East Hampton, New York

The Pollock-Krasner House is a unique site and should be on any must-see list.

The Pollack-Krasner House

4. Where should a first-time visitor stay in East Hampton?

For places to stay, there are a number of charming inns and B&Bs along Route 27 in East Hampton. The Maidstone Hotel, The Hedges Inn, and 1770 House are among them, and their locations are ideal for walking into town or to Main Beach. The Maidstone provides free bikes for guests to use to explore.

The Maidstone Inn in East Hampton, New York

The 1770 House in East Hampton, New York

The Hedges Inn, East Hampton, New York

5. What’s your favorite shop in town?

Village Hardware.  It has all the essentials for a homeowner. Others might vote for Bookhampton, The Monogram Shop, or any of the fashionable boutiques along Newtown Lane and Main Street.

Main Street, East Hampton, New York

6. Favorite beach?

Main Beach is our favorite ocean beach and Maidstone Park is our favorite bay beach.

7. Favorite restaurant?

Cove Hollow Tavern is a relatively new restaurant that is a real crowd pleaser; we always leave there happy. EMP Summer House is also really good. For quick bites and snacks, Citarella and the Golden Pear in town and the Main Beach Pavillion are all good.

Cove Hollow Tavern, East Hampton, New York

8. Tell us about life in East Hampton – what clubs do long-time residents belong to, where do they like to spend their time?

The Maidstone Club and the Devon Yacht Club are still the primary social clubs for the old guard.  The Blue Book of the Hamptons (which is like the local Social Register) only recognizes those two clubs in town. Some of the newer money has joined the East Hampton Golf Club.  Those who dock their expensive boats in town can be found dining at East Hampton Point on Sunday afternoons.

The Maidstone Club, East Hampton, New York

East Hampton Point

9. What’s the preferred car in East Hampton?

The Jeep Grand Wagoneer “Woody” is always a head turner. The Mercedes GL450 is the family car of choice.

10. Who would we be surprised to learn has a house in East Hampton?

Beyoncé is the latest mega-celebrity to purchase a home here so that may still be a surprise to some.

11. Describe the East Hampton vibe in three words.

Pretty, artistic and self-aware.

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