Hamptons Vacation Guide: 15 Important Things To Know Before Booking Your Getaway

The Hamptons can be an interesting juxtaposition between two worlds. Here you can find celebrities and nightclubs mixed with mom-and-pop shops and farm stands.

Residents include the mega rich, surfers, and the families descended from farmers, whalers, and fishermen here before Long Island Railroad came through and changed South Fork forever. 

The Hamptons can, and should be, a wonderful vacation destination. But if you’re unprepared it may feel hectic, crowded, and leave you wondering “Where did my time go?”

I spent a year living in the Hamptons and learned a lot during that time!

Here’s what you need to know before booking your Hamptons getaway, plus tips regarding where to stay and what to do!

Hamptons Vacation Guide

Where are the Hamptons?

The Hamptons are a collection of hamlets on the far east end of Long Island about 90 miles from New York City.

The area stretches from Westhampton to Montauk, with about an hour and a half drive between the two.

Where to Stay in the Hamptons

Roughly 20 hamlets form the Hamptons. The main vacation locations and best places to stay being Bridgehampton, East Hampton, Sagaponack, Sag Harbor, Westhampton, Southampton, Wainscott, Water Mill, Montauk, and Amagansett. 

If you wish to see and be seen, enjoy trendy restaurants, nightlife, and designer shops you’ll love the villages of Southampton and East Hampton.

If a younger crowd, surf-vibe, top-notch nightlife, and close proximity to the beach are your thing, check out Montauk for your Hamptons weekend getaway.

If you’re looking for a family friendly spot, or just something a little quieter check out Sag Harbor or Westhampton.

No matter where you decide to stay you’ll find luxury boutique hotels, there are no chain hotels in the Hamptons. A few popular hotels are:

• Topping Rose House in Bridgehampton
• Capri Hotel in Southampton
• Faraway Sag Harbor (formerly Baron’s Cove) in Sag Harbor
• Gurney’s Montauk Resort & Seawater Spa in Montauk.
• The Reform Club in Amagansett.

Most hotels book far in advance and have a minimum stay requirements in the peak summer season. 

Airbnb and VRBO rentals are also available but may be limited.

For lots more information regarding where to stay in the Hamptons check out: Where To Stay In The Hamptons.

What Is The Nicest Part Of The Hamptons?

There truly are no bad places to stay in the Hamptons. However if you’re looking for celebrity sightings, designer shops, and top-notch nightlife, you’ll want to plan your Hamptons vacation in East Hampton or Southampton.

When Should You Visit The Hamptons?

Memorial Day to Labor Day is prime season for the Hamptons. This is the only time of year the weather is nice enough to hit the beaches for swimming and sunbathing.

If you’re looking to enjoy nightlife and restaurants, summer weekends are for you.

If you’re hoping for a quieter experience with relatively less crowds, you’ll be much happier booking your Hamptons getaway during the week. 

Off-Season In The Hamptons

Shoulder seasons, April – May and September – October, can be great times to visit. The weather is still nice but the crowds thin out significantly. It may be too cold for swimming but still nice enough to lounge on beach chairs in a cozy sweater.

Fall has become increasingly popular with fun activities such as fall festivals, pumpkin patches, and the Hamptons International Film Festival.

Be aware that April and May can be very rainy, September and October are dry but there is the possibility for hurricanes.

Winter in the Hamptons is the complete opposite from summer. Along with chilly temperatures you’ll find plenty of space to relax and unwind without another soul in sight. Many restaurants and businesses close after the holidays and remain so until about April.

Don’t let that deter you from visiting though, a Hamptons vacation in winter can be very relaxing and quite affordable compared to the rest of the year. Check out my list of Top Things To Do In The Hamptons In The Winter for more ideas!

How Many Days Do You Need In The Hamptons?

You’ll want a minimum of two days in the Hamptons. Getting to the Hamptons can be a long process depending where you’re coming from, be sure to factor this in.

Four to five days here would be ideal. This allows you to spend plenty of time at the beach plus take a day trip or two to the surrounding hamlets.

Getting To The Hamptons 

From NYC

Getting to the South Fork of Long Island from NYC is easy! Hop on the Long Island Rail Road or Jitney bus, both have many departure times and drop off locations. Each option requires about 2 – 3 hours.

Otherwise, drive straight down the Long Island Express, just be weary of traveling during peak times. A two hour drive can easily turn to four on a Friday afternoon — not a great way to start your Hamptons weekend getaway!

If you’re feeling fancy and want to skip the slow transportation options consider taking a helicopter or seaplane via BLADE. This will have you in the Hamptons in less than an hour.

Ferry

If visiting from the north, various ferry routes will take you to Orient Point on the North Fork or Montauk. From there rent a car or arrange a ride.

Flying In 

JFK and LaGuardia are the nearest major airports to the Hamptons. After landing follow the “from NYC” above instructions upon landing. 

Flying into Islip, a small regional airport primarily serviced by Southwest Airlines, will cut your drive time in half. From the airport plan to rent a car and head out on the 45 minute drive or hop on the Long Island Railroad.   

For lots more information be sure to check out How To Get To The Hamptons.

Getting Around The Hamptons

Getting to this beach destination without a car is easy, but once you’re here you’ll probably need one. There’s no public transportation and while Uber and cabs are available they aren’t always timely.

The Hamptons are full of narrow and winding two lane roads and nothing is “just around the corner.” What may appear to be a short drive down Montauk Highway is often a process thanks to traffic.

If you’re set on not renting a car check out hotels offering ride services or stay in a central location which allows you to bike everywhere needed. 

Is It Possible To Visit The Hamptons On A Budget?

I’ll be honest, this isn’t the easiest vacation destination to visit on a budget. Having said that, nothing is impossible! Here are a few tips for planning a Hamptons vacation on a budget:

• Visit during the off-season, even shoulder seasons such as spring and fall will see lower prices than summer. Winter is by far the most affordable time of year to visit the Hamptons.
• Check out hotels and summer rentals in quieter Hamptons hamlets such as Springs, North Sea, Quogue, and Noyack.
• If possible, rent a home with a large group of friends or family to cut the high price of lodging.
• Walk, bike, or catch a ride to the beach.
• Avoid dining out and expensive nightlife. Even replacing a few meals and drinks with supplies from the grocery store will save tons over a long weekend.
• Check out free activities or local events in the hamlet you’re staying in. Some popular free activities include farmers markets, Tuesday’s at Main Beach for live music, Hamptons Fine Art Fair, etc.

Hamptons Beach Guide

The beaches here are a bit complicated, regulations vary in different areas, some rules change on the weekend, etc. The below information will give you a general overview, but be sure to do research based on the exact beach you plan to visit during your Hamptons vacation.

There are private, residential, and public beaches around the Hamptons. Private and residential beaches are off limits for most.

The public beaches are free and open to everyone (yay!) however it’s difficult to get parking passes. Annual passes are prioritized for residents and need to be purchased before the season begins.

Some beaches have daily parking passes, which run you about $30, but most don’t offer this option.

Don’t fret! This doesn’t mean you can’t go to the beach. The public beaches are still free and accessible to anyone without a parking pass. However you will need to walk, bike, or get a ride. 

Note: Your hotel or rental will usually provide information regarding which beach you can visit.

Best Beaches In The Hamptons

All Atlantic Ocean facing beaches in the Hamptons are excellent, and more or less the same, in my opinion. Again, I’d choose a beach near your hotel or rental to avoid spending time in traffic. A few of the most popular beaches in the Hamptons are:

• Coopers Beach in Southampton – one of the most visited beaches in the Hamptons.
• Main Beach in East Hampton – another much-loved option, they have a small restaurant and bar on site.
• Mecox Beach in Bridgehampton – popular, centrally located beach.
• Atlantic Avenue Beach in Amagansett – relatively quiet beach near East Hampton.
• Ditch Plains in Montauk – very popular beach known for some of the best surfing in the Hamptons.
• Long Beach (Foster Memorial Beach) in Sag Harbor – one of the few bay-facing spots with a true beach. This is the most family-friendly beach in the Hamptons thanks to calm waters. It’s also ideal for water sports and distance swimming.

Regardless of which beach you plan to visit these are a few helpful tips:

Not all Hamptons beaches have lifeguards.

Beach amenities are limited to a simple snack bar and restrooms if anything.

Thanks to favorable currents the water surrounding Long Island is surprisingly warm! If planning to swim be aware that Atlantic facing beaches can have very rough waves. If you’d rather skip the big waves, head to a beach on the South Fork’s northern shore such as Long Beach in Sag Harbor.

Keep an eye out for dolphins, humpback, and fin whales which have made a return to the area in recent years. During my summer in the Hamptons we saw whales very frequently from June – August.

If visiting the beach on a summer weekend it’s best to arrive by 10 am to ensure a good spot — and trust me you’ll want a good spot, these are some of the best beaches in the United States!

What To Wear In The Hamptons

Wondering what to pack for your Hamptons vacation? It might be a bit more laid-back than you imagine. Underneath all the rosé and hoopla is a relaxed beach town and the dress here reflects that.

Airy summer attire like cotton pieces, maxi dresses, linen sets, and classic prints such as polka dots and nautical stripes are always perfect for summer in the Hamptons.

While you do want to get dressed up for dinner, wine tastings, or a popular event, you probably don’t need to get as dressed up as you think. The Hamptons style is elegant but laid-back, even for most formal events.

For more ideas and details regarding what to wear during your Hamptons vacation check out my full guide: What To Wear In The Hamptons.

The Best Things To Do During Your Hamptons Vacation

Now that you’ve got the logistics worked out it’s time to enjoy your Hamptons getaway! Below are a few of my favorite things to do in the Hamptons:

• Head to Wölffer Estate Vineyard for a wine tasting (they’re famous for their rosé!).
• Sail Sag Harbor or check out the docked yachts.
• Shop at the high end stores in East Hampton or Southampton.
• Browse the Parrish Art Museum.
• Watch the surfers at Ditch Plains or tour Montauk Point Lighthouse in Montauk.
• Indulge in all that your appetite desires, whether from a fancy restaurant or local farm stand.
• Dig your toes into the sand at the most popular Hamptons beaches.
• Grab a lobster roll from LUNCH.
• Catch a live show at the Surf Lodge or Stephen Talkhouse.
• Visit LongHouse Reserve or the Pollock-Krasner House in East Hampton and Springs.

For more ideas, check out The Best Things To Do In The Hamptons.

Are The Hamptons Worth Visiting?

Simply put, yes.

In addition to incredible beaches the Hamptons really have something for everyone.

If you’re looking for surfing and rowdy nightlife, head to Montauk. If you want to shop at high-end stores and catch a polo match head to Southampton or East Hampton. If you wish to sail or stroll a charming main street with historic homes, Sag Harbor is for you.

I hope this post assists you in planning an incredible Hamptons vacation! Any questions? Please leave a comment below!

Looking for more ideas? Below are additional Hamptons and New York guides.

More Information For Your Hamptons Vacation:

• Amagansett Guides
• East Hampton Guides
• Montauk Guides
• Sag Harbor Guides
• Southampton Guides
• North Fork Guides
• Best Wineries In The Hamptons
• Where To Stay In The Hamptons
• How To Get To The Hamptons
• What To Wear In The Hamptons
• Spring In The Hamptons: Top Things To Do
• Summer In The Hamptons: Top Things To Do
• Fall In The Hamptons: Top Things To Do
• Winter In The Hamptons: Top Things To Do
• Christmas In The Hamptons: Top Things To Do