Plan Ahead: What to Book Early for Your Summer in the Hamptons
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Plan Ahead: What to Book Early for Your Summer in the Hamptons
Dreaming of your summer on the East End? Whether it’s your first time visiting or you’re a Hamptons regular, booking early is key to locking in the best experiences. Here’s what fills up quickly, and how to plan ahead for an unforgettable season.
Where to Stay
Accommodations in the Hamptons book up fast, especially for holidays and weekends. Hamptons Vacation Inn opens its doors May through October (stay tuned), and many of our cottages are reserved weeks (even months!) in advance.
Popular peak weekends to reserve early:
Memorial Day Weekend (May 23–26)
Fourth of July Week
Labor Day Weekend (Aug 29–Sept 1)
📝 Stay tuned to our Instagram for updates.
Wineries & Tastings
Many local vineyards, like Wölffer Estate, Duck Walk, and Macari—require reservations for tastings, especially on weekends. Summer concerts, sunset events, and wine dinners fill quickly.
Need inspiration? Explore our Dining & Activities Guide to help build your itinerary.
Dinner Reservations
Spots like Nick & Toni’s, Jean-Georges, and Sant Ambroeus are summer staples that book out for weeks. Consider booking through Resy or OpenTable as soon as your trip dates are confirmed.
Want something more casual? Check out our Best BBQ Spots and Coffee Shop Guide.
Activities & Transportation
Ferry Tickets (to Shelter Island or Montauk): Reserve early for cars & bikes.
Fishing Charters & Boat Tours: Especially popular from Sag Harbor or Montauk.
Whale Watching Tours: See our full Whale Watching Guide
Stay Tuned for Our 2026 Opening Season
While we’re currently closed for the season, we’re already preparing for another unforgettable summer on the East End.
📲 Follow us on Instagram @hamptonvacation for:
Opening announcements
First access to early booking alerts
Weekly curated guides to events, dining, and hidden gems in the Hamptons
Your next escape starts here, see you in 2026! 🐚