The Hamptonites

24–48 Hours in the Hamptons: The Ultimate Weekend Guide (2025)

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Southampton • Water Mill • Bridgehampton • Sag Harbor Edition

Planning a weekend trip to the Hamptons? This curated 1–2 day Hamptons itinerary covers everything you need: beach spots, brunch favorites, local walks, casual bites, and unforgettable dinners.

Because let’s face it – I know visiting the Hamptons can be stressful enough. Between figuring out sheer logistics (do we fly and then drive? train? Hampton Jitney? Helicopter), finding a place to stay (10/10 do not recommend trying to find a hotel last minute in July unless you’re planning on spending away your future child’s college fund) and then treavel logistics once you get here (surprise! The Hamptons are shockingly a bit spread out), there’s a lot ot consider – and that’s before you get to the fun stuff.

But hey – that’s where I come in. Between myself and my friends, I have years of experience for do’s and don’t’s for weekend trips from my 20s. I’ve got your back – so read on for a must do, 48 hours in the Hamps.

Morning: Where to get breakfast / Coffee

We’ve all been there. Early Saturday AM, a bit of a headache (or okay, sometimes a lot of a headache), and all your body needs is carbs and caffeine to kickstart the day. Fear not – the Hamptons is no short supply of fantastic coffee and bagel shops to make that hangover a distance memory (or, if you’re better than us all and made it to a 5am Barry’s bootcamp in East – you’re body also needs some coffee and carbs. See, we’re not that different!)

Bagel Energy

Goldberg’s Famous Bagels (Southampton • Water Mill • Sag Harbor)
A local favorite for good reason. Get the classic New Yorker with lox and pair it with an iced matcha latte or iced dulce de leche latte. In season, expect a bit of a wait here, especially at their South location. But trust me – it’s worth it.

French-Vibes Bakery Stop

Armin & Judy Bakery (Bridgehampton): Feels like a quick trip to Paris, with all the comforts of home. Grab the pain aux raisins or a warm croissant and an iced coffee and you’re ready to seize the (pool) day.

Next-Level Breakfast Taco & Much More

Hampton Coffee Company (Multiple locations)
One of my favorite spots (it even made my Top 20 Hamptons Restaurants!), if you’re feeling up to a bit more than a grab and go, Hampton Coffee never disappoints. If near Watermill, they even have a full sit down area with all of the classics, plus my favorite – the Mexican breakfast tacos – here are unforgettable. Add a cold brew with oat milk = chef’s kiss or matcha latte.

Pro tip: Hampton Coffee has seasonal shaken cold brews that always fit the vibe (I can’t tell you why, but coconut shaken cold brew just hits different in the summertime)

Midday: Beach & Scenic Drive/Walk

Hit the Beach: Our Favorites

  • Flying Point Beach (Water Mill’s main beach)
    • Drive a bit further along past Flying Point Beach to the end of Flying Point Road to reach “The Cut” Beach. At this beautiful local spot, the ocean beach meets Mecox Bay for an unforgettable experience.
  • Gibson Beach (Sagaponack) – Quiet, scenic, and perfect for photos due to the scenic drive there with expansive farms (think rolling hay and horses).
    • Dog friendly before 9am and after 6pm in the summer! Pass by lavender fields en route when in season.

Hot Girl Walk / Scenic Drive Routes

  • Gin Lane & Meadow Lane (Southampton) – Immerse yourself amongst the lines of perfectly cut privet and oceanfront home architecture. Make sure to weave in and out of the beautiful side streets such as Wyandanch Ln.

👉 [Check out my full beach & walk guide → The Ultimate Hamptons Beach List]

Farmstand Hopping & Lunch

Lobster / Seafood Go-To

Lunch / Lobster Roll (Southampton): Need I provide an explanation why a lobster roll is necessary for lunch? Dine in casual with a cold dress or grab it to go on your way to the beach.

Our Fave Gourmet Grab-and-Go

  • Citarella (Southampton)
  • Round Swamp Farm (Bridgehampton)
  • Sagaponack General Store (Sagaponack)

Farmstand hop using our 👉 Quick Guide to the Top 5 Farmstands in the Hamptons

Dinner Time (Our top 3 picks)

👉 Want more options? Check out full list –> The 20 Ultimate Must Try Hamptons Restaurants 2025 Guide

Dopo Argento: Our Favorite Italian (Southampton)

One of my go-to’s, time and time again, no matter the season. On main street in Southampton, it provides the perfect mix of “see and be seen”, while also providing top tier Italian dining and service. Stylish yet cozy, with outdoor seating in front and back and a lively bar scene inside, Dopo Argento serves a short-list of tailored Italian cooking with phenomenal cocktails – you can equally stop in for just a drink an a quick appetizer or stay for while, enjoying those cool summer evenings on the patio with a fantastic pasta and a nice martini in hand.

Don’t miss: Fresh Oysters, (dirty) martinis, Wagyu meatballs, and any pasta (you deserve it!)

T-Bar: Quintessential American (Southampton)

The second T-Bar opens, run don’t walk because before you know it summer is over and they are wrapping up the season. *Sigh for a wishing this fabulous place was open all year*. With a stunning garden patio with a retractable canopy, lively bar & valet parking, and oh – did I mention it’s dog friendly? Could T-Bar get better? Don’t think so! Make a reservation because it gets packed!

Don’t miss: Classic burger, turkey burger, zucchini pizza (thin strings of zucchini on top of cheese no sauce, so unique), margarita pizza, and the duck

Elaia Estiatorio: Authentic Greek with a Post Dinner DJ (Bridgehampton)

My top pick for Greek food in the Hamptons. Between the cozy, approachable but elevated ambience and their wide ranging menu to serve all your Greek food desires, you’ll feel transported to Greece (if even just for an hour). Everything I have gotten here has been phenomenal, Expect fresh seafood, lively DJ at certain hours, and a packed bar.

Don’t miss: Grilled chicken skewers and any seafood dish. The mezzes, pita, branzino, moussaka.

Sweet Stop

Sant Ambroeus (Southampton)

If you did not get dessert while out to dinner. Save time for a short walk in Southampton Village and stop by Sant Ambroeus for a gelato. Try the pear sorbet. It’s delicate, refreshing, and unforgettable. My go to after dinner treat any night of the week.

After Dinner Cocktail

Looking for a place to “go out without going out”? Post dinner check out Calissa (Water Mill) for a cocktail + DJ vibes. Calissa features a DJ in the Lounge on Friday and Saturday evenings year-round. On summer Sundays, Calissa hosts live music on the Terrace. Check out their Entertainment page for details on featured events and summer lineup.

Day Two: Grounding & Nature Before Heading Home

Start with Coffee in Sag Harbor

Ease into your morning with a caffeine fix in Sag Harbor. Two of my favorites?

  • Grindstone Coffee & Donuts: A local staple, known for its small-batch roasted coffee and melt-in-your-mouth donuts. A quick, pop in and grab and go type of place.
  • Sagtown Coffee: Sleek, cozy, and reliably good – it’s the kind of spot where you’ll run into both locals and weekenders. I always get their oatmilk latte on draft – cannot be beat!

Take your coffee (and donuts) to go and enjoy a stroll along the marina — it’s peaceful in the early hours, with the yachts quietly bobbing in the harbor.

Morning Nature Walk: Elizabeth A. Morton Wildlife Refuge

If the weather is on your side, head to Elizabeth A. Morton National Wildlife Refuge for a dose of nature and quiet. The trail meanders through woodlands and leads to a stunning stretch of bay beach. Bring a camera — or simply soak in the views.

It’s the kind of hidden gem that reminds you why the East End is so special.

Lunch + Local Shopping

After your walk, refuel with lunch in Sag Harbor or head over to Southampton for a change of scenery. A few tried-and-true picks:

  • In Sag: Lulu Kitchen & Bar for wood-fired fare or The Beacon if you’re lucky enough to catch a seat overlooking the water. If you are looking for something grab and go, stop into Carissa’s Bakery for a sandwich (try the smoked salmon or mortadella) + sweet pastry.
Carissa’s Bakery – Sag Harbor
  • In South: Sant Ambroeus for chic café vibes, or Tutto il Giorno for something elegant yet unfussy (both places we have raved about as part of our Ultimate Top 20 Hamptons Restaurants) .

After lunch, take your time browsing the boutiques — Sag Harbor’s Love Shack Fancy, DÔEN, or Southampton’s main street of shops (too many to list – B&ASH, Tenet, Veronica Beard, Lake, Ralph Lauren) never disappoint.

A Last Sip Before You Go

If you’re catching a late ferry or driving back after sunset, squeeze in one last moment of Hamptons magic with a glass of wine at:

  • Channing Daughters in Bridgehampton — more low-key and artsy, with whimsical sculpture gardens and lesser-known varietals.
  • Wölffer Estate in Sagaponack — iconic, picturesque, and perfect for golden hour. Their outdoor patio is a dream.

Sip slowly, take it all in, and toast to a weekend well spent.

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Welcome to the hamptons!

Lauren here – former weekender turned full-time Hamptonite. Now in my 30s, I’m proud to call the East End home year-round. This guide is my love letter to the place that captured our hearts — beyond the beach days and beyond the season.

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