undefined Itinerary

Rent a bike from Rotations Bicycle Center and take a scenic ride through the Hamptons, passing by stunning estates and picturesque farmland. Stop for lunch at The Lobster Roll, a casual seafood shack that has been serving up fresh lobster and clam chowder since the 1960s.

After lunch, head to the Southampton Historical Museum to learn about the area's rich history, including its connection to the Titanic. Then, take a drive to the nearby town of Sag Harbor, where you can browse the charming shops and galleries.

For dinner, head to 75 Main, a trendy restaurant known for its lively atmosphere and delicious food. Try their famous truffle fries and a glass of wine from their extensive wine list.

Take a day trip to nearby Shelter Island, accessible via ferry. Spend the morning hiking through the Mashomack Preserve, a nature sanctuary with stunning views of the water.

After your hike, enjoy a picnic lunch on the beach or head to Sunset Beach, a chic hotel with a lively beach club scene. Relax on the beach or take a dip in the crystal-clear water.

For dinner, head to Vine Street Cafe, a farm-to-table restaurant serving up fresh, seasonal dishes. Be sure to try their homemade pasta and local seafood.

Spend the morning at Cooper's Beach, one of the most beautiful beaches in the Hamptons. Relax on the sand and soak up the sun, or take a dip in the ocean.

After the beach, head to the Wolffer Estate Vineyard for a wine tasting and tour. Sample their award-winning wines and enjoy the beautiful views of the vineyard.

For dinner, head to the Southampton Social Club, a lively restaurant and bar with a great outdoor patio. Try their signature lobster mac and cheese, and stay for the live music and cocktails.

Take a surfing lesson at Flying Point Surf School, one of the best surf schools in the Hamptons. Learn the basics of surfing and catch some waves.

After your lesson, head to the nearby town of Bridgehampton for lunch at Estia's Little Kitchen, a charming cafe serving up delicious Mexican and Mediterranean-inspired fare.

For dinner, head to the iconic 1770 House, a historic inn and restaurant known for its farm-to-table cuisine and cozy atmosphere. Make sure to try their famous chocolate souffle for dessert.