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Luxurious 5-Day Getaway in The Hamptons, New York Itinerary
Last updated: 2024 Jun 14Historic Southampton and Culinary Delights
Morning
Begin your Hamptons adventure with a delightful breakfast at Sant Ambroeus East Hampton, known for its elegant ambiance and Italian pastries. Afterward, immerse yourself in the history of the area with the Southampton Scavenger Hunt, which will take you to some of the most iconic spots in Southampton.
Afternoon
For lunch, head to Hampton Chutney Co. for a unique South Indian dosa experience. Post-lunch, spend a leisurely afternoon at the Cooper's Beach, one of the most pristine beaches in the area. Relax, take a dip, or simply bask in the Hamptons sun.
Evening
As the day winds down, enjoy a sophisticated dinner at 1770 House Restaurant & Inn, housed in a historic building. Afterward, take a stroll through the charming village of Southampton and explore its boutiques and art galleries.
Bedtime
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Southampton Scavenger Hunt
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Art, Nature, and Gourmet Eats
Morning
Fuel up for the day with a breakfast at The Blend At Three Mile Harbor, offering a serene waterfront setting. Post-breakfast, visit the Parrish Art Museum, a stunning space housing a diverse collection of American art.
Afternoon
Lunch beckons at Nick & Toni's, a local favorite for its wood-fired pizzas and Mediterranean-inspired dishes. After a sumptuous meal, spend your afternoon exploring the beautiful gardens and estate of the LongHouse Reserve, a hidden gem of the Hamptons.
Evening
Dine in style at The Palm - East Hampton, known for its prime steaks and caricature-adorned walls. Cap off the evening with a sophisticated cocktail at The Bays Bar & Grill, enjoying the view of the harbor as the sun sets.
Bedtime
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Montauk's Natural Wonders and Coastal Cuisine
Morning
Start your day with a hearty breakfast at The Station Bar, a local spot with a laid-back vibe. Then, head to the Montauk Point Lighthouse, the oldest lighthouse in New York State, and enjoy the breathtaking views of the Atlantic Ocean.
Afternoon
For lunch, savor the seafood at The Lobster Roll Restaurant, also known as "Lunch," a Montauk institution. Post-lunch, spend a relaxing afternoon at Ditch Plains Beach, a popular spot for surfers and beach lovers.
Evening
As the day winds down, have dinner at Sam's Restaurant, where you can enjoy fresh, locally sourced dishes. Afterward, experience the vibrant nightlife of Montauk at The Surf Lodge, known for its live music and energetic atmosphere.
Bedtime
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Shelter Island Serenity and Gastronomic Delights
Morning
Enjoy a tranquil breakfast at 18 Bay Restaurant, which offers a farm-to-table dining experience with a view of the water. Afterward, take a morning stroll through the Mashomack Preserve, one of the richest habitats in the Northeast.
Afternoon
For lunch, head to Vine Street Cafe, a charming spot known for its diverse wine selection and delectable cuisine. Post-lunch, explore the island further with a visit to the Shelter Island Historical Society, where you can learn about the area's rich history.
Evening
Dine at {R-The Tavern], located at the historic Ram's Head Inn, and indulge in their classic American fare. After dinner, enjoy a peaceful evening walk along Wades Beach, known for its calm waters and beautiful sunset views.
Bedtime
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Montebello Lakes and Chiflon Day Tour from San Cristobal
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Sag Harbor's Maritime Heritage and Epicurean Pleasures
Morning
Begin with a breakfast at Lulu Kitchen & Bar, offering a cozy atmosphere and a menu inspired by the South of France. Afterward, take a guided tour of the Whaling Museum, where you'll learn about Sag Harbor's rich maritime history.
Afternoon
For lunch, head to Dockside Bar & Grill, a casual spot with a great view of the harbor. Afterward, explore the boutiques and art galleries of Sag Harbor's Main Street, or take a relaxing cruise on the Hampton Luxury Liner for a different perspective of the area.
Evening
Conclude your Hamptons journey with a memorable dinner at Tutto Il Giorno, known for its elegant ambiance and authentic Italian cuisine. After dinner, enjoy a nightcap at {R-The Beacon], where you can sip on cocktails while overlooking the harbor.
Bedtime
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