Ultimate Hamptons Weekend Itinerary

From beautiful beaches to boozy brunches, we’ve handpicked all the must-see spots for your next Hamptons getaway.

Here’s the ultimate weekend itinerary for the Hamptons, 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 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.

Let us know if you have any questions or need further recommendations. We’d be happy to assist you!