Hamptons Weekend Getaway: Our Ultimate Itinerary
From beautiful beaches to boozy brunches, we’ve handpicked all the must-see spots for your next Hamptons getaway.
Planning a Hamptons weekend getaway? Here’s our ultimate weekend itinerary, curated for a mix of luxury, beach relaxation, local charm, and unforgettable food.
Friday – Arrival & Sunset Vibes
Afternoon
• Arrival: Aim to arrive by 3–4 PM to beat traffic & make the most out of your getaway. Hint- always ask for an early check-in if possible. We’d be happy to accommodate this for a small charge.
• Check-in: Get acquainted with your Hamptons vacation rental, unpack and check out the views.
• Home Suggestions: Sprawling Southampton Home, East Hampton Retreat, Classic Southampton Home.
Evening
• Sunset Cocktails: Head to Rumba in Hampton Bays for drinks with a view. Take the boat over to Cowfish for round two.
• Dinner:
• Cowfish (Hampton Bays) – seaside, lively.
• Rumba (Hampton Bays) – chill, coastal vibe.
• Optional: Nightcap at Stephen Talkhouse in Amagansett (live music & local energy).
Saturday – Hamptons in Full Bloom
Morning
• Breakfast: Grab a coffee and pastry at Jack’s Stir Brew or Carissa’s Bakery.
• Beach Time:
• Main Beach (East Hampton): iconic and pristine.
• Cooper’s Beach (Southampton): great amenities. Voted best beach in America.
• Optional Activity: Surfing lesson, paddle boarding, or yoga on the beach
Midday
• Lunch:
• Lunch Lobster Roll (Amagansett): iconic roadside seafood
• Tutto il Giorno (Southampton or Sag Harbor): upscale Italian
• Shopping & Exploring:
• Boutiques in East Hampton or Sag Harbor
• Visit LongHouse Reserve or Parrish Art Museum for some local culture
Evening
• Golden Hour: Wine tasting at Wölffer Estate Vineyard (sunset in the vines is a must).
• Dinner:
• Nick & Toni’s (East Hampton) – celeb-loved, upscale rustic
• Pierre’s (Bridgehampton) – French flair
• Optional: Bonfire on the beach (check local rules or go with a private concierge setup)
Sunday – Wind Down in Style
Morning
• Check-out: Pack up your things and but don’t bid the Hamptons farewell. Take the scenic route home with a few staple stops along the way.
• Brunch:
• The Maidstone (East Hampton) – chic and cozy
• Bell & Anchor (Sag Harbor) – seafood-forward brunch
• Stroll: Walk around Sag Harbor Marina, or rent bikes and explore quiet lanes.
Midday
• Art & Culture Stop:
• Guild Hall in East Hampton
• The Church in Sag Harbor (creative arts space)
• Last Stop Beach Picnic: Grab goods from Round Swamp Farm or Cavaniola’s and head to the beach.
Late Afternoon
• Departure: Avoid traffic by leaving before 5 PM if driving, or take an evening train/Jitney back to NYC.
Pro Tips:
• Book restaurants and wineries in advance: weekend spots fill up quickly.
• Bring layers; nights can get breezy.
• Bike rentals or scooters are a fun way to avoid traffic and explore quaint streets.
Where to Stay for Your Hamptons Weekend Getaway
Base yourself in Southampton. Most of our Hamptons vacation rentals are in and around Southampton and Shinnecock Hills, right between Hampton Bays (Friday’s sunset drinks) and East Hampton and Sag Harbor (Saturday and Sunday), so every stop on this itinerary is an easy drive. Several homes come with a private pool or hot tub, which makes the downtime between plans part of the trip. Check each listing for its minimum stay, since some homes are set up for longer visits.
Ready to make the weekend yours? Browse our luxury Hamptons rentals, from village homes with heated pools to beach cottages a short walk from the sand.
Let us know if you have any questions or need further recommendations. We’d be happy to assist you!
