A Weekend in SouthamptonDiscover Southampton, New York's charm! Spend a weekend exploring pristine beaches, boutique shops, and gourmet dining. Unwind in luxurious accommodations and embrace coastal bliss 🏖️AuthorsSteller
DestinationsSouthamptonItinerary

Stays

The Mainstay
This charming boutique hotel offers rooms with modern amenities and coastal elegance. Plus, it is centrally located near shops, restaurants, and beaches.
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Southampton Inn
In the heart of downtown, this charming inn offers elegant rooms, superb amenities, and easy access to local attractions.
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Capri Hotel Southampton
A boutique hotel offering stylish rooms and suites with modern amenities. Enjoy its convenient location near the beach and downtown area.
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Guided Excursions

Guided Farm and Wine Country Bike Tour in Mattituck NY
Explore renowned vineyards where you can sample award-winning wines amidst picturesque vineyard landscapes. Book this tour for an enriching wine-tasting experience!
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Luxury Beach Bonfire and Picnic Dinner at Town Line Beach
Indulge in a beachfront dinner prepared specially for you! Book this this unforgettable dining experience for romance and relaxation in equal measure 🌟
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Friday

Shinnecock Lobster Factory
A great lunch spot. Order their signature lobster roll, served with buttery brioche, or try the classic New England clam chowder!
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Tate's Bake Shop
Visit the famous Tate's Bake Shop (yes, the one you're thinking of)! At 20+ years old, this place is still a favorite for their iconic, crispy cookies.
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Southampton History Museum
Learn about the history of this area... Complete with interactive exhibits and replicas!
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Hildreth’s
An 180+ year old department store, famous for fun window displays... They have everything you could need for your home, but is also fun to just browse.
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Breezin' Up
Stop in for any Hamptons gear and souvenirs you could want or need.
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Saturday

Golden Pear Cafe
Start your day here with a freshly brewed coffee and a warm pastry!
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Sean's Place
The perfect spot for grab and go sandwiches to bring with you to Coopers Beach. They have gluten free wrap options too.
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Cooper's Beach
Definitely the most popular beach in Southampton! There are umbrellas and chairs for rent. The beach faces the Atlantic so waves can be rough, be careful.
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Sip'n Soda
After a long day of fun in the sun, stop at this classic diner (opened in 1958) for some ice cream before dinner! Only on vacation ;)
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Tutto Il Giorno South
Enjoy authentic Italian cuisine. Start with their bruschetta and then move on to their wood fired pizzas 🍕
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Sunday

Four Oaks Cafe & Juice Bar
Stop in for a morning juice, coffee, and quick bite before heading to the beach for the day.
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Flying Point Beach
Enjoy sunbathing on soft sands, swimming in the waters, or surfing the Atlantic's waves 🏖️
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Milk Pail U-Pick Farm
A family-owned and operated farm, stop by for fresh produce, cider, and doughnuts!
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Blu Mar Hamptons
Enjoy seafood with Mediterranean flair on your last evening in Southampton. Try the grilled octopus and branzino dishes. Dine on the outdoor terrace overlooking the water.
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