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I just got back from a long weekend trip to the Hamptons for the first time and had the BEST stay! Even though I’m a bit behind on my international trip blog coverage from this spring, I felt so inspired from my time on Long Island, I’m bumping this post up in my queue! The Hamptons is a quintessential girls weekend getaway — accessible from both NYC and New England via the Amtrak and ferry, and full of the most aesthetic cafes, shops, waterfront restaurants, beach clubs, and so much more. This guide is going to cover exactly how to get there, where you should stay, and how you should spend your time exploring the many quaint and picturesque towns. Here’s your guide to a perfect Hamptons weekend.
Where Are The Hamptons?
The Hamptons are located on the South Fork of Long Island, about ~100 miles east of New York City. These seaside villages are known for their beaches, charming downtowns, glitzy shopping, insanely expensive real estate, and the occasional celebrity sighting. Although many people refer to “the Hamptons” as a single destination, it’s actually made up of several distinct communities, each with its own vibe. The below list covers basic info about the most visited towns:
Amagansett
Amagansett is a laid-back beach town known for its quiet coastline, farm stands, and more of a relaxed, local feel.
Bridgehampton
Bridgehampton is a quieter, more rural-feeling Hamptons town known for horse farms, vineyards, and boutique shopping.
East Hampton
East Hampton is very “classic Hamptons” and has insane luxury homes, a lively village center full of luxury stores like Prada and Louis Vuitton, and more beaches.
Montauk
Montauk sits at the far eastern tip of Long Island (at the “end of the world”) and is known for its surfing, marina, and laid back beach town vibe. There’s a beautiful lighthouse here!
Sagaponack
Sagaponack is one of the most exclusive Hamptons villages, known for its sprawling farmland and ultra-luxury estates near the ocean. I love the general store here!
Sag Harbor
Sag Harbor is a historic harbor town filled with waterfront dining, yacht clubs, and a charming downtown.
Southampton
One of the main towns in the Hamptons, known for its upscale Main Street and iconic beaches like Cooper’s Beach.
Best Time To Visit The Hamptons
The best time to enjoy a Hamptons weekend is from late May through early September, when the weather is warm, beach clubs are open, and the towns are fully alive with restaurants, events, and more. For fewer crowds and better rates, late spring and early fall (May, September, and early October) are ideal while still offering pleasant coastal weather — plus there are some fun events in the fall, such as the Annual Harvest Party at Wölffer Estate Vineyard.
How To Get To The Hamptons
From New York City:
Hampton Jitney
The Hampton Jitney is a comfortable, direct bus from Manhattan into Hamptons towns like Southampton, East Hampton, and Montauk. Book early as this a popular way to travel for a Hamptons weekend in the summer. Tickets are $30-75ish each way.
Long Island Rail Road (LIRR)
The LIRR runs from Penn Station or Grand Central directly to Hamptons stops like Westhampton, Southampton, East Hampton, and Montauk, and will cost around $20-45 each way.
From New England:
New London, CT → Orient Point Ferry
From Boston, I took the Amtrak from Back Bay into New London, CT (about 1.5 hours and cost about $50ish). Then, walked 5 minutes down the road to the New London Ferry Terminal. The Cross Sound Ferry runs hourly from New London, CT to Orient Point, NY and takes a little over an hour. The ferry was about $25 each way.
Pro-tip: Although Orient Point is technically on Long Island, it is located in the northern part, quite far from the main Hamptons towns. There are a series of bays that separate the North & South Forks, and they do NOT have bridges (despite looking like you can cross over Shelter Island on the map), meaning you have to go all the way around via car or the public bus. I rode the public bus and it took almost 3 hours to travel from the ferry terminal to Bridgehampton.
Montauk Ferry
There is also a ferry from Montauk to New London, CT but it runs much less frequently and is a seasonal route. However if you’re staying on the eastern end of the Hamptons, I highly recommend checking the times on the Viking Fleet website. I was able to ferry back to CT on Sunday evening at the end of my Hamptons weekend and avoided the long public bus ride again! This ferry is a bit more expensive and cost about $60 one way.
Where To Stay In The Hamptons
For your Hamptons weekend, I recommend staying in one of the main towns and bopping around! My friends have stayed in Southampton area in the past, but this time we stayed in Sagaponack and I really loved it! We were only 15 minutes to East Hampton, 10-15 minutes from Bridgehampton, and less than 30 from Southampton, meaning we were easily able to visit several towns in just one weekend.
The Hamptons is NOT cheap. Boutique hotels here can cost upwards of $800 for just one night. I definitely recommend bringing some friends and making a girls weekend getaway out of it to split the cost.
My friends and I stayed at The Sagaponack Hotel and loved it! This is a newly renovated, design-forward boutique hotel set across 7 acres with bungalows, a pool, and beach amenities. They have bikes for rent, beach passes, free snacks & coffee, and the location was perfect. I highly recommend you stay here during your Hamptons weekend.
The Perfect 3-Day Hamptons Itinerary
East Hampton & Sag Harbor: Day 1
- Arrive by ferry into Orient Point or Montauk from New London, CT
- Lunch at the Golden Pear Café on Main Street
- Afternoon at the beach or strolling Main Street (loved the boutiques here!)
- Sunset rooftop cocktails at the hidden Green Room Bar, which is on the third floor of the Sag Harbor Cinema
- Dinner in Sag Harbor on the water at Le Bilboquet. It’s known for its chic yacht club views and lively summer atmosphere (reservation required and cocktail attire preferred!)
Southampton & Amagansett: Day 2
- Breakfast & shopping along Southampton’s Main Street (there’s a Golden Pear Cafe here too… Justin Bieber’s fav!)
- Browse the Southampton Farmers Market on the Town Green
- Afternoon at the Palm Tree Music Festival (June annual event) featuring acts like Kygo, Chainsmokers, and Disco Lines, plus brand activations, food, and VIP upgrades (worth it for bathrooms, food/drink access, and included drinks)
- If visiting outside of the festival weekend, head to Stephen Talkhouse in Amagansett for live music and nightlife instead!
Sagaponack & Montauk: Day 3
- Breakfast at Sagaponack General Store (breakfast burritos + iced vanilla lattes in a very aesthetic, historic setting)
- Morning yoga at Wölffer Estate Vineyard’s “Yoga in the Vineyard” (~1 hour outdoor class, ~$40)
- Wine tasting at Wölffer Estate Vineyard, including the “Summer in a Bottle” flight, charcuterie, and flatbreads
- Afternoon stop at the Ralph’s Coffee pop-up truck in East Hampton to chill in the sun
- Drive out to Montauk for a late-day stroll through downtown
- Dinner at Rooted Mediterranean by the marina
- Ferry back to Connecticut to end your Hamptons weekend
My Hamptons weekend really lived up to the hype—beautiful beaches, charming towns, great restaurants, fun bars, etc! It’s especially perfect for a girls trip, with a mix of beach days, shopping, and long, vibey dinners.
One final note — make sure to book accommodations and reservations in advance, especially in the summer when things fill up quickly. It’s definitely an expensive destination (think $10 iced coffees and $200 shirts in boutiques). However, a weekend in the Hamptons really is one of the best coastal trips from NYC or New England.
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