The Ultimate Guide to the Hamptons

If there’s one thing I get asked about the most, it’s the Hamptons. I wouldn’t call myself a veteran, but I am somewhat knowledgeable about what to do and wear out there. My parents started taking my brothers and me out there when I was young. While a lot has changed—especially with influencers running wild in Montauk—I still consider it one of the greatest places on Earth.

Rather than sending out a brief recommendations list, here’s a deep dive into the questions I get asked most.

1. What do I wear?

People really go all out when it comes to getting dressed out there. Stick with neutral colors. I love a classic blue-and-white striped long‑sleeve shirt out east. Linen dresses, skirts, straw hats, and sandals are staples. Many women wear dresses to the bar, and you’ll rarely spot anyone in jeans unless it’s daytime. Go big or go home with your accessories.

2. Where in The Hamptons should I go?

Honestly, it depends on the vibe you want.

Westhampton is great if you’re staying on Dune Road. I can’t speak to Quogue or Hampton Bays, but if you’re hungry and still have an hour left on your drive, definitely stop at Francesca’s.

Southampton is more my territory. Stroll through town to explore the cute shops, or head to Cooper’s Beach to soak up the sun. If you have time, visit the Parrish Art Museum.

For all Bethenny Frankel fans, Bridgehampton is where you’ll want to stop to pick up chicken salad from Round Swamp Farms. I’d also recommend the chicken fingers and cookies.

Sag Harbor is a must‑see. Shop your way down historic Main Street, then stop for pastries at Carissa’s The Bakery and enjoy them across the street at one of the picnic tables while admiring the docked boats.

Those looking for an extreme shopping spree should head to East Hampton. Every designer store you can imagine is in town—just make sure you’re ready to open your wallet.

Few people stay in Amagansett unless they own a home there. If you’re looking for live music, make your way to The Stephen Talkhouse.

Last but not least is Montauk. If you want to be like every other person that moved to the city and posts about life out east, spend the weekend here. When I was younger, the town was family‑oriented, but now it’s overrun by city visitors. You can splurge at the Surf Lodge—just be prepared to spend more than your week’s paycheck—or stick to the bars in town.

3. Where should I go to eat?

The Hamptons is VERY expensive and the Ubers are $80 to go 10 miles. I would recommend making your dinner reservations a month out in advance.

Here are some of my favorites:

• Montauk

  • Duryea’s - Dinner

  • Joni’s - Breakfast

  • Bird on the Roof - Breakfast/Lunch

  • Montauk Brewing Company - Drinks

  • Montauk Bake Shoppe - Breakfast

  • Fudge N Stuff - Dessert

• Amagansett

  • The Clam Bar - Lunch/Dinner

  • The Lobster Roll - Lunch/Dinner

  • Fini Pizza - Lunch/Dinner

  • Amber Waves Farm - Breakfast/Lunch

• East Hampton

  • Moby’s - Dinner

  • Highway - Dinner

  • Bostwick’s Chowder House - Lunch/Dinner

• Bridgehampton

  • Armin and Judy - Dinner

• Sag Harbor

  • Lulu Kitchen & Bar - Dinner

  • Sen - Dinner

  • BuddhaBerry - Dessert

  • Vin Sur Vingt Bistro - Dinner

  • Kidd Squid Brewing Company - Drinks

• Southampton

  • Tutto IL Giorno South - Dinner

  • Shinnecock Lobster Factory - Lunch/Dinner

  • Local Burger - Dinner

  • The Fudge Company - Dessert

  • Cheese Shoppe - Breakfast

• Hampton Bays

  • Rumba - Dinner

  • Cowfish - Dinner

4. Where do I go out?

Everyone wants to go to Surf Lodge, it’s just a fact. There’s plenty of other places to go out.

• The Stephen Talkhouse

• Wolffer Estate Vineyard

• Shagwong

• The Point

• Memory Motel

• Murf’s Backstreet Tavern

5. Where should I take a workout class?

There are tons of workout classes out there. If you want to spend $58 on a class, head to Barry’s in Southampton or Wainscott. New York Pilates has studios in almost every town, and there are plenty of SoulCycle locations as well. For those who want to stick to their city roots, you can work out at the Tracy Anderson Method.

I’m very fortunate to have spent my summers out east. When I’m there, I’m reminded of the little girl I once was—riding her bike with her brothers down Montauk Highway to get Goldberg’s.