5 Days in The Hamptons Adventure Itinerary

Begin your second day with a visit to Cooper's Beach in Southampton. This beach is often ranked among the best in America and offers soft white sand and gentle waves. After enjoying some beach time, have breakfast at Tate's Bake Shop, famous for its cookies but also offering a variety of breakfast options.

In the afternoon, visit the Parrish Art Museum which features an impressive collection of American art from the 19th century to present day. It's an excellent place to immerse yourself in culture and creativity. For lunch, head over to Little Red, known for its casual yet sophisticated dining experience.

Spend your evening exploring Southampton Village with its charming streets lined with shops and cafes. Don't miss out on visiting some of the historic sites such as Halsey House or Thomas Halsey Homestead. For dinner, make reservations at Sant Ambroeus, an elegant Italian restaurant that offers both indoor and outdoor seating.

Start your third day by taking part in Greenport Village Rides: Your Full-Day Driver Service. This tour provides you with a personal driver who will take you around Greenport Village allowing you to explore this charming area at your own pace without worrying about transportation logistics.

After enjoying your morning tour around Greenport Village continue exploring on foot or bike if you prefer! Visit Mitchell Park which has beautiful waterfront views along with attractions like antique carousel rides! For lunch try out Noah's where they serve up fresh seafood dishes that are sure not disappoint!

As evening falls take advantage of more free time provided by driver service from earlier today - perhaps venture further out into North Fork Wine Country where numerous vineyards await discovery! End night dining at The Frisky Oyster renowned spot offering creative takes on classic American fare paired perfectly local wines.

Begin your day with a visit to the Montauk Point Lighthouse, the oldest lighthouse in New York State. The panoramic views of the Atlantic Ocean from the top are breathtaking and provide a perfect start to your day. After exploring the lighthouse, head over to John's Pancake House for a hearty breakfast. Their pancakes and omelets are local favorites.

In the afternoon, take a hike through Camp Hero State Park. This park offers a mix of wooded trails and oceanfront paths, making it ideal for nature lovers. The park also has historical military installations that add an interesting twist to your hike. For lunch, stop by The Lobster Roll, famously known as 'Lunch', where you can enjoy fresh seafood in a casual setting.

As evening approaches, visit Ditch Plains Beach, known for its excellent surfing conditions and stunning sunset views. It's a great spot to relax and unwind after an active day. For dinner, dine at Duryea's Lobster Deck, which offers delicious seafood dishes with beautiful waterfront views.

Greenport Village Rides: Your Full-Day Driver Service will be available again today to take you around Sag Harbor and its surroundings. Start your morning with a visit to the Sag Harbor Whaling & Historical Museum where you can learn about the village's rich maritime history. Afterward, have breakfast at SagTown Coffee, known for its cozy atmosphere and excellent coffee.

In the afternoon, explore Mashashimuet Park which offers lovely walking trails and recreational facilities. It's a peaceful place to spend some time outdoors. For lunch, try out Bay Burger, famous for their juicy burgers made from locally sourced ingredients.

Spend your evening strolling along Main Street in Sag Harbor with its charming shops and galleries. Don't miss out on visiting the iconic American Hotel which has been serving guests since 1846! For dinner on your final night in The Hamptons, make reservations at The Beacon, offering stunning harbor views along with delectable dishes made from fresh local produce.