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Travel
A Jonathon Hawes Guide to the Hamptons
The Hamptons offer something for every taste and season. Whether you’re lounging on the beach, exploring a winery, or cozying up by the fire, it’s all about enjoying the simple pleasures in life—elevated, of course. Welcome to my Hamptons—let’s dive in!

If you know me, you know I love the Hamptons. It’s not just a destination—it’s an experience that feels equal parts chic and grounding. I’ve always been drawn to the Atlantic, whether it’s exploring the rugged beauty of the Maritimes or the windswept coast of Brittany in France. But the Hamptons? It’s where coastal charm meets history and effortless style.

Growing up, I was lucky enough to visit places like Nova Scotia, Prince Edward Island, and Newfoundland. The Hamptons remind me of everything I loved about the Maritimes, with an extra dash of sophistication.

This stretch of Long Island has roots steeped in history. Before it became synonymous with summer elegance, it was home to the Shinnecock Nation. Later, European settlers turned this coastal haven into farming villages and built a legendary whaling industry. By the late 19th century, the area’s beauty caught the eye of New York’s elite—artists, writers, and socialites who transformed sleepy harbours into chic cultural hubs. Today, it’s the perfect mix of old-world charm and modern indulgence, from lavender fields and farm stands to luxury boutiques and world-class dining.

Let me take you through my guide to the Hamptons—what to do, where to eat, and, of course, where to stay.

What to Do in the Hamptons: Season by Season

 

Spring

  1. Visit Local Farm Stands
    Spring is the perfect time to explore the Hamptons’ renowned farm stands. Amber Waves Farm in Amagansett and Pike Farms in Sagaponack are both fabulous for fresh produce and artisanal goods.
  2. Explore the Madoo Conservancy
    This Sagaponack gem is a dream in spring, with blooms everywhere. It’s an enchanting spot for a quiet stroll.

Summer

  1. Relax at the Beaches
    Whether it’s East Hampton Main Beach or Wainscott Beach, the Hamptons’ pristine coastline is legendary. Pack a picnic, your chicest sun hat, and plenty of sunscreen.
  2. Dine Al Fresco
    Summer is all about dining outdoors. Almost every patio feels like a postcard, and it’s the perfect time to sip rosé while soaking up the sunshine.

Fall

  1. Apple and Pumpkin Picking
    Nothing says fall like Hank’s Pumpkintown in Water Mill. Apples, pumpkins, and even corn mazes—it’s the ultimate autumn activity.
  2. Visit Local Wineries
    Wölffer Estate Vineyard in Sagaponack is a favourite of mine. Their rosé is famous, and the vineyard is stunning during harvest season.

Winter

  1. Cozy Up Indoors
    There’s nothing better than renting a little cottage with a wood-burning fireplace. Curl up with a good book, catch up on writing, or binge-watch your favourite shows.
  2. Stock Up at Loaves & Fishes
    Their prepared meals are perfect for a cold winter day. I always leave with soups and casseroles, ensuring I don’t need to venture out if the weather is frightful.
Where to Eat in the Hamptons

Breakfast

  1. Carissa’s The Bakery
    Bougie and fabulous, this spot at 221 Pantigo Road is my go-to for flaky croissants and chic tartines. Their Sag Harbor location is perfect for coffee and pastries.
  2. John Papas Café
    If you need something hearty after a long night, this is the place. Their club sandwiches are perfect!
  3. Goldberg’s Bagels
    Nothing beats their bagel and lox before a beach day—it’s a Hamptons classic.
  4. The Golden Pear
    Ideal for a quick, chic breakfast on-the-go. Their hazelnut coffee is a must!

Lunch

  1. Le Bilboquet (Sag Harbor)
    A sunny patio, a glass of rosé, and their signature Cajun chicken—it’s Hamptons chic at its finest.
  2. The Clam Bar (Napeague)
    This roadside gem is all about lobster rolls, fried clams, and salty seaside charm.
  3. The Lobster Roll aka “Lunch” (Amagansett)
    A retro seafood shack that serves nostalgia on a plate—lobster rolls, creamy chowder, and the perfect beach vibe.
  4. Sant Ambroeus
    Elegant Italian classics and the best cappuccino to finish.
  5. 75 Main (Southampton)
    Perfect for fresh seafood, vibrant salads, and prime people-watching.

Dinner

  1. The 1770 House (East Hampton)
    A quintessential Hamptons experience. Their cozy tavern and famous meatloaf make it my absolute favourite.
  2. East Hampton Grill
    Their ribs and heavenly biscuits are a meal unto themselves. Add a martini, and you’re set.
  3. The American Hotel (Sag Harbor)
    Timeless and elegant, with an incredible wine list and Dover sole prepared to perfection.
  4. Tutto il Giorno
    Chic Italian sophistication with divine pastas and seasonal seafood.
  5. Topping Rose House
    Farm-to-table perfection in a beautifully restored setting.
Where to Stay in the Hamptons
  1. The 1770 House (East Hampton)
    This historic inn holds a special place in my heart. I’ve stayed here in every season, and it’s magical every time—especially in late summer, fall, and winter. The rooms are beautiful, and the restaurant is simply divine.
  2. The Baker House 1650 (East Hampton)
    For luxury and tranquility, this elegant bed-and-breakfast is unbeatable. Their gardens and spa make it an oasis.
  3. Topping Rose House (Bridgehampton)
    A full-service luxury experience with chic rooms and an exceptional Jean-Georges restaurant.
  4. The Bridgehampton Inn & Restaurant (Bridgehampton)
    Rustic elegance with a renowned on-site restaurant that celebrates seasonal, local ingredients.