Remember the bright, colourful towns from Gossip Girl? Lush green lawns, blooming flowers, bright beaches, bonfires, luxurious parties, and boutiques? The Hamptons are filled with people who look straight out of a J.Crew catalog, all enjoying that summer vibe. This issue is your guide to an Old Money style weekend getaway for New Yorkers: Long Island.

The Hamptons in Long Island is famous for being the summer playground of New York's rich and famous: owning a summer house here is the line between the wealthy and the common folk. The Hamptons combine the charm of the countryside with luxury, the scent of the sea with the aroma of fine wine. Lavish villas and private beaches are practically the trademarks of this area. Many towns on Long Island have preserved elements from the 18th and 19th centuries, making them perfect for those who love old-town charm and natural scenery.

Easy Peasy Transportation

Whether you're driving or taking the LIRR, it’s super convenient and only takes 2-3 hours from Manhattan. 

The Hamptons include East Hampton, Bridgehampton, Southampton, and Montauk at the far end of the island. Each place has a unique vibe, blending relaxation with elegance, which is what Hampton Style is all about.

• Cooper Beach in Southampton is known for its soft white sand and dunes.

• LongHouse Reserve in East Hampton features a sculpture garden and art gallery, merging art with nature's unique beauty.

• Wölffer Estate Vineyard offers wine tasting, vineyard tours, and seasonal activities (like yoga), all with stunning views.

• South Fork Natural History Museum and Nature Center lets visitors get hands-on with starfish, crabs, sea urchins, and other sea creatures, with exhibits featuring local wildlife and aquariums.

• Main Beach in East Hampton is another beautiful beach.

• Carissa's the Bakery serves up creative baked goods and coffee, with three locations on Long Island.

• Egypt Beach is a quieter spot, perfect for sunset photos and relaxation.

• East Hampton Library showcases Hampton's artistic style with colonial revival symmetry, classic columns, and traditional materials, blended with European arch windows, stone fireplaces, intricate woodwork, antique furniture, and timeless designs.

• East Hampton Main Street is packed with designer brands and boutiques like Tiffany & Co., plus plenty of art galleries.

• CHANEL Hamptons Seasonal Boutique & Ralph Lauren Home are also on Main Street, with stunning store designs.

• Home Sweet Home Museum is a must-visit for history buffs, housed in an 18th-century saltbox home with colonial revival style, showcasing 18th and 19th-century antiques, porcelain, and memorabilia of John Howard Payne. The garden features gardening styles from mediaeval to 19th-century America and Europe.

• The Stephen Talkhouse is a well-known local live music venue.

Note: The Hamptons get super crowded during summer weekends. The long lines, crowds, and traffic jams are not just urban myths! One-day trips are not recommended.

Montauk: The Surf Town

Located at the easternmost tip of Long Island, the cute, lively Montauk is dubbed the "Fishing Capital of the World," offering rich fishing experiences and seafood.

• Montauk Point Lighthouse is a 200-year-old lighthouse commissioned by George Washington himself and is the fourth oldest in the U.S.

• Left Hand Coffee at 83 S Elmwood Ave, Montauk is a delightful little café in downtown. 

• Hither Hills State Park offers seaside campsites, nature trails, bike paths, and opportunities for fishing and hunting.

• Ditch Plains is a surfer's paradise, known for its excellent surfing conditions.

• Deep Hollow Ranch is a historic horse ranch where you can experience beachside horseback riding, with customized services based on riding experience.

• Lobster Roll Restaurant is a must-visit classic in Montauk for their famous lobster rolls.

• Montauk Brewing Company is a can’t-miss for drink lovers! 

• 668 The Gig Shack offers a variety of American and Mexican dishes, with live performances in the evenings.

• The Surf Lodge features live music and a bar, and also offers accommodation.

• Montauk Music Festival takes place every May, featuring four days of diverse music genres, including rock, pop, blues, and jazz, with performances on outdoor stages, restaurants, and bars.

Where to Stay

If you prefer not to stay in the Hamptons, Montauk is a great alternative with cheaper accommodations and plenty of cute cafes and shops.

• Montauk Manor, is a historic mansion built in 1927, offering budget-friendly studios for as low as $100 during off-peak times.

Note: If you're planning a day trip to Montauk without driving, be aware of train schedules as the LIRR runs only one train per day.

Sag Harbor: Yacht Central

At Sag Harbor, you can see the rich folks' toys – boats and luxurious yachts docked at the harbour.

• Sag Harbor Books 

• The American Hotel, built in 1846, is a historic old spot with a blend of classical and modern interior design. It features eight unique guest rooms, each with different antiques and decor. Even if you're not staying there, the hotel's restaurant offers a mix of American and French cuisine and boasts an impressive 85-page wine list.

• Sag Harbor Farmers Market is open every Saturday from 9 AM to 1 PM from May to September.

• Tanger Outlets Riverhead is a nearby mall for those looking to shop.

Stay tuned for more details in Part 2!