How to Plan the Best Trip to the Hamptons

This blog post will help you plan your trip to the Hamptons.

Thinking of planning a trip to the Hamptons this summer? You’re going to love it.

Whether you’re escaping the New York summer heat, planning a beachy road trip, or just craving cute cafes, charming seaside towns, and lobster rolls on tap, this Hamptons guide is for you.

I recently did an East Coast road trip with stops all along Long Island, and the Hamptons ended up being one of my favourite parts.

I even made a full YouTube vlog dedicated to our trip to the Hamptons (East Hampton, Southampton, Bridgehampton, and Sag Harbor), and put together an eBook travel guide covering the full road trip if you want to download it!

So if you want to plan a trip to the Hamptons for the first time, or you’re trying to figure out what to do in the Hamptons for a day (or a full weekend), here’s everything you need to know. Including where to eat, stay, shop, and explore in each of the main towns.

This blog post is all about how to plan a trip to the Hamptons

How to Get to the Hamptons from New York City

Getting to the Hamptons from NYC is super easy, and you’ve got a few solid options depending on your budget and how much time you’ve got.

1. By Car (East Coast Road Trip Style!)

Driving is my personal favourite way to get to the Hamptons and was how I made my way there on both of my trips. We rented a car with Rental cars and highly recommend them – so easy and affordable!

You get to roll the windows down, blast a summer playlist, and stop at cute roadside stands along the way.

If you’re doing a road trip to the Hamptons or heading out for the weekend, leaving early in the morning or later in the evening will help you skip the worst traffic.

It usually takes 2-3 hours depending on where you’re headed.

2. By Train (LIRR)

Hop on the Long Island Rail Road from Penn Station. It’s comfy, affordable, and drops you off right in the heart of towns like Southampton or East Hampton.

Perfect if you’re doing a day trip to the Hamptons from New York.

3. By Bus (Hampton Jitney or Hampton Luxury Liner)

The Hampton Jitney is a bit of a local legend and if you’ve watched Gossip Girl, you’ll know all about the Hampton Jitney.

It’s an iconic way to travel on your trip to the Hamptons from NYC, and the onboard snacks and WiFi definitely don’t hurt. It’s super convenient and can take you straight into Montauk, Sag Harbor, and further.

Hamptons Itinerary: Best Places to Visit in the Hamptons

Each town in the Hamptons has its own vibe, so part of the fun is discovering which one fits your ideal vacation mood.

Some are posh and elegant, others are boho and beachy. All of them are gorgeous in their own way.

Here’s a breakdown to help you plan the perfect trip to the Hamptons itinerary:

1. East Hampton

East Hampton felt like the perfect mix of classy and coastal. It’s stylish but still has that relaxed small-town energy. We wandered around the cute town centre, browsed boutique shops, and strolled down to Main Beach, which is just picture-perfect.

East Hampton gives you that quintessential Hamptons feeling. Tree-lined streets, shingled houses with white hydrangeas, chic cafes, and boutique shopping galore. It’s polished but never pretentious.

Things to Do in East Hampton:

Lounge on Main Beach (one of the prettiest beaches in the Hamptons!)
Visit the East Hampton Main Street Historic District
Spend a morning at Guild Hall for art exhibitions
Stroll through the charming village centre

Where to Eat in East Hampton:

Carissa’s Bakery – Hamptons famous and so good!
Nick & Toni’s – iconic and a celebrity fave
Cove Hollow Tavern – laid-back but still upscale

Where to Stay in East Hampton:

The Baker House 1650 – gorgeous, romantic B&B vibes
The Huntting Inn – a historic inn that’s walkable to everything

If you’re planning a trip to the Hamptons as part of an East Coast road trip, make sure to download my East Coast road trip eBook to help you plan and book your trip with ease!

2. Sag Harbor

Sag Harbor is full of charm and has more of a storybook feel. It’s got cobblestone streets, sailboats bobbing in the marina, and a really rich maritime history.

It’s a little artsy, a little old-money, and super walkable which makes it perfect for a relaxed afternoon or romantic weekend. I spent Thanksgiving here a few years ago on my first trip to the Hamptons and loved it.

It’s one of the most picturesque towns in the Hamptons with a strong local vibe. It’s less flashy than some of the other areas, and has a great balance of history, culture, food, and natural beauty.

Things to Do in Sag Harbor:

Browse the local shops and bookstores
Visit the Sag Harbor Whaling & Historical Museum
Catch a show at Bay Street Theater
Grab an ice cream and walk the docks at sunset

Where to Eat in Sag Harbor:

Dock House – perfect spot for lobster rolls right by the water
Il Capuccino – cozy Italian restaurant that locals love
Page Sag Harbor – farm-to-table, upscale but unfussy

Where to Stay in Sag Harbor:

Baron’s Cove – classic Hamptons hotel with a pool and marina views

Sag Harbor Hamptons NY — *My first visit to Sag Harbour at Thanksgiving*

3. Montauk

Montauk is the laid-back, beachy cousin in the Hamptons crew. It’s a surfer’s paradise, full of sandy toes, beach bars, and summer energy. If you’re into sunsets, seafood shacks, and crashing waves, Montauk’s your spot.

It’s ideal if you want your trip to the Hamptons to feel like a beach vacation. It’s chill, scenic, and has more of a California coastal vibe than the other towns.

Things to Do in Montauk:

Visit the Montauk Point Lighthouse (probably the most iconic spot in the Hamptons)
Go hiking at Camp Hero State Park (gorgeous ocean views!)
Chill at Ditch Plains Beach with a book or a surfboard
Take a boat tour or try deep-sea fishing

Where to Eat in Montauk:

The Lobster Roll – iconic, casual, and so tasty
Duryea’s – lobster, rosé, and the best views
668 The Gig Shack – funky, fun, and great for live music

Where to Stay in Montauk:

Marram Montauk – minimalist design right on the beach
The Surf Lodge – cool, colourful, and a hotspot for weekend vibes

4. Southampton

Southampton is glam with a capital G. It’s upscale, elegant, and full of designer shops, historic mansions, and well-manicured everything.

If you want to lean into the luxury side of your trip to the Hamptons, this is the place.

It’s one of the most iconic areas in the Hamptons and perfect for a luxe weekend escape. It’s got the feel of an old East Coast summer town with all the modern perks.

I might have browsed Chanel and Gucci while I was here, but I came away with a jumper that said ‘Southampton’ on it. My wallet much preferred the merch store!

Things to Do in Southampton:

Visit the Southampton Arts Center or Parrish Art Museum
Window shop along Jobs Lane and Main Street
Spend a few hours at Cooper’s Beach

Where to Eat in Southampton:

Sant Ambroeus – chic and classic
Tutto Il Giorno – rustic Italian in a beautiful setting
Golden Pear Café – great for a relaxed breakfast or lunch

Where to Stay in Southampton:

Southampton Inn – centrally located and charming
The 1708 House – historic and beautifully restored

5. Bridgehampton

Bridgehampton hits a sweet spot between rustic and refined. Think farmers markets, vineyards, and horse farms mixed with boutique hotels and brunch spots. It’s a little quieter than the main Hamptons hotspots but totally worth visiting during your trip to the Hamptons.

It’s less touristy and feels more “local summer.” There’s an artsy side here too, and the scenery is just gorgeous.

Things to Do in Bridgehampton:

Visit the Bridgehampton Museum for a look at local history
Sip wine at Wölffer Estate Vineyard
Stop at the weekly farmers market for fresh produce and baked goods
Enjoy a beach day at Mecox Beach

Where to Eat in Bridgehampton:

Almond – buzzy bistro with great cocktails
Pierre’s – charming French-American menu
Bobby Van’s – a steakhouse that’s been around forever

Where to Stay in Bridgehampton:

Topping Rose House – a luxury stay with a spa and Jean-Georges restaurant onsite

Unique Things to Do in the Hamptons

If you want to go beyond the usual beach day and boutique browsing, here are a few fun and unique things to do in the Hamptons:

Book a sunset sail from Sag Harbor
Take a cooking class at Loaves & Fishes Foodstore
Go horseback riding at Deep Hollow Ranch (the oldest working ranch in the US!)
Cycle the beach roads between East Hampton and Amagansett
Visit the Pollock-Krasner House for an artsy afternoon
Explore the Bridge Gardens – a peaceful spot for a slow stroll

Best Time to Visit the Hamptons

The Hamptons really shine in the summer months (June–August), which is when you’ll get the full experience: sunny beach days, open-air restaurants, live music, and weekend markets.

July and August are peak season, so expect bigger crowds and higher prices.

If you’re planning a trip to the Hamptons on a budget, late spring (May) and early autumn (September) are amazing alternatives. It’s quieter, cheaper, and still warm enough to enjoy the outdoors. Just make sure to bring a light jacket for cooler evenings.

Instagram-Worthy Spots in the Hamptons

Let’s be honest, you’re going to want to capture everything on your trip to the Hamptons. Here are some of the best photo spots for your Hamptons feed:

Montauk Lighthouse at sunset – dramatic cliffs + golden light = perfect shot
Main Beach in East Hampton – especially early in the morning when it’s empty
Wölffer Estate Vineyard – the vines, the terrace, the wine glass in hand, everything is a vibe
The Surf Lodge – stylish, colourful, trendy, and super photogenic
Sag Harbor dock at sunset – boats + golden hour magic

Bring a cute hat or linen shirt for your photos. Anything light and breezy looks amazing against those summery backdrops!

How to Vacation in the Hamptons on a Budget

Your trip to the Hamptons doesn’t have to be all luxury hotels and pricey seafood towers. With a bit of planning, you can definitely enjoy a vacation in the Hamptons on a budget:

Go midweek for better prices on accommodation
Opt for charming B&Bs or motels instead of big resorts
Pack picnic lunches to enjoy at the beach or in local parks
Use public transport or bike rentals to get around
Explore all the free beaches, hikes, and nature spots!

What to Do in the Hamptons for a Day

Just got a day to spare? Here’s a quick-hit trip to the Hamptons itinerary:

Morning train or Jitney to East Hampton
Grab coffee at Carissa’s and wander through town
Spend a few hours relaxing on Main Beach
Head to Montauk for late lunch at The Lobster Roll
Explore the lighthouse and grab sunset drinks at The Surf Lodge
Head back to NYC with sandy feet and a full heart

Our Hamptons to Rhode Island Ferry Experience

One of my favourite travel days from our East Coast road trip was driving through the Hamptons to our next destination. We took three ferries from Shelter Island across to Rhode Island.

It was such a peaceful, scenic crossing (and a bit unexpected!). From there, we continued our East Coast road trip to Providence and Boston, which felt like the perfect continuation after the sun-soaked beachy vibes of the Hamptons.

If you’re planning a longer road trip, I highly recommend combining your trip to the Hamptons with stops in Rhode Island and coastal Massachusetts. It’s such a gorgeous part of the US.

RELATED blog post to read: 15 Things to do in Providence, Rhode Island

How to Plan a Trip to the Hamptons

Planning a trip to the Hamptons is like prepping for the ultimate summer escape.

Whether you’re going solo, with friends, or as a couple, this little stretch of New York coastline has a way of making every day feel special. Between the beach days, sunset dinners, lazy brunches, and breezy drives, a trip to the Hamptons is equal parts glam and grounding.

Don’t forget to check out my YouTube vlog for a real-life peek into my Hamptons road trip, and download my East Coast Road Trip eBook guide for even more tips, budget-friendly ideas, and inspiration for your summer adventures.

So pack your cutest linen outfits, don’t forget sunscreen, and get ready to fall in love with the Hamptons.

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By Orlagh Shanks

Orlagh Shanks is the Editor of Orlagh Claire, an award-winning travel and lifestyle blog.
After working in the PR & Influencer Marketing industry, Orlagh quit her job to travel Asia for 12 months and move to Sydney, Australia where she is now a full-time travel blogger and content creator sharing travel tips and recommendations for all 30 of the countries she’s visited so far.

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This blog post is all about how to plan a trip to the Hamptons