Your Guide to Planning the Ultimate Getaway to The Hamptons

February 28, 2023 • By Amy Jo Robertson


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Looking for the perfect vacation getaway? Look no further than the Hamptons! The Hamptons is a collection of towns and villages in the state of New York, on the eastern end of Long Island.

You don’t need to be an A-list celebrity to visit the Hamptons. Families, sports fans, and history buffs frequent this area to explore the state parks, surf, or just take in the striking home designs.

Do you feel like a holiday in the Hamptons is out of reach? Not anymore! House swapping has emerged as a new form of inexpensive travel that makes the Hamptons getaway affordable for every family. Keep reading to learn more about how you can secure your house in the Hamptons for your next vacation.

How to Get to the Hamptons

Westhampton, Hampton Bay, Southampton, Bridgehampton, East Hampton, Amagansett, and Montauk are stops on the Long Island Railroad. You can book a ticket on this train and travel to the Hamptons by foot or taxi during your stay.

If you choose to drive, you will take the Long Island Expressway until it terminates in Riverhead, at which point you should turn south onto Route 27, which will take you all the way to Montauk.

Busses are available every day. Even with traffic congestion during rush hour, the entire drive takes around 3 and a half hours. Expect to pay about $30 for each trip if you choose to travel by bus.

Where to Stay in the Hamptons

The Hamptons are the ultimate getaway for recreation and rejuvenation. Although many deem a trip to the Hamptons as a venue for the elite, it’s also an accessible getaway for family fun. Once you have settled in the Hamptons as your vacation spot, you need to decide where you want your swapped house to be located. 

The Hamptons is made up of two towns, East Hampton and Southampton. Pick your destination based on what experience you are looking for. Both will assure you of an amazing vacation while offering starkly different amenities.

East Hampton offers a laid-back location full of sunsets, relaxation, and beach vibes. The Hamptons may be notorious for high-profile events, but East Hampton offers an elevated “beach town” vibe. The town is littered with local artists and small businesses.

Southampton serves as a mecca for luxury. From polo matches and galas to expansive estates, the wealth and prestige associated with Southampton radiate for miles. If you want to spend your vacation living large, this is the perfect spot for your holiday. 

Alternatively, you can go a little further out and stay near Westhampton Beach. This spot is not officially considered part of “the Hamptons,” although its beaches and storefronts mirror that of a traditional Hampton experience.

Bask in the Sun on the Best Beaches

The beaches in the Hamptons are world-renowned for their views and activities. The best beach to visit when staying in the Hamptons depends on how you choose to travel into town and where you are staying. Here are some of the beach highlights in the Hamptons.

There are several possibilities for paid day parking lots if you aren’t staying directly in the heart of the Hamptons. One of the Hamptons’ most infamous beaches is Cooper’s Beach. Cooper’s Beach is a long, broad beach with facilities located in Southampton.

Foster Memorial Beach, also known as Long Beach in Sag Harbor, is the best option for swimmers who want calm, shallow waters or to be closer to the sand. This idyllic sandy stretch also makes for the perfect sunset viewing spot accessible to the public. 

If your family is looking for a day full of outdoor activities, Kirk Park Beach is the perfect spot. The beach is covered in magnificent sand dunes that will give you an exclusive peak at whales breaching offshore. Kirk Park Beach also has a hiking trail that will let you enjoy your beach day from land.

The best beach for the all-American beach vacation is Atlantic Avenue Beach in Amagansett. It is available to the public, is dog friendly, and features lifeguards, food stands, bathrooms, and a surf break. This is perfect for families with kids wanting to spend the day at the beach.

Pack Your Itinerary

The Hamptons offers so many different activities for the whole family to enjoy. There are a plethora of options to fill your itinerary when visiting the Hamptons. The area is also infamous for outdoor activities to keep you active and going all day!

If you want to enjoy a leisurely stroll in nature, be sure to visit Sagaponacks’ Madoo Conservancy. These beautifully designed gardens create a fantastic landscape. The Madoo Conservancy has been dedicated to the preservation and enhancement of its whimsical and horticulturally diverse gardens for the past 60+ years.

If you want to spend the afternoon being active, you can rent a bike and cycle down to the Montauk Point Lighthouse in South Fork. The Montauk Point Lighthouse is the state’s oldest lighthouse that lets you soak in nautical history and amazing views.

Over the years, the Hamptons have become a breeding ground for artistic ingenuity and creative safe-havens. The works of Jackson Pollock and Lee Krasner are on display at their home in East Hampton.

At the Hamptons, you can even explore a rich variety of marine life at the Long Island Aquarium. This aquarium is home to the largest all-living coral reef display in the Northern hemisphere. Every aquarium is carefully curated to ensure a fun experience for all its visitors. 

Explore the East Coast’s Wine Options

Winery tours and wine tastings are the perfect opportunities to learn more about local history while indulging in a nice glass of wine. The Hamptons has several wineries that let you escape from the beach and garden parties for a little while.

Go down Bridgehampton’s Scuttle Hole Road to Channing Daughters Winery’s seated tastings. It’s usually packed due to its delicious array of wines, so it’s best to make a reservation in advance.

Shelter Island’s new wine bar has been creating quite the buzz. The White Oak Wine Garden has live music and a variety of alcoholic beverages, including wine flights, beer, and even mulled wine.

Plan extra time in your itinerary to visit the Wölffer Estate Vineyard in nearby Sagaponack. This vineyard is known for its rosé options. If you’re looking for something a little stronger, you can even mosey on over to the Sagaponack Farm Distillery.

Grab a Bite

No trip to the Hamptons is complete without a mouthwatering meal. From local bakeries to world-class dining establishments, the Hamptons offers an array of dining options at a variety of price points.

Carissa’s Bakery in East Hampton is known for its warm olive ciabatta bread. It has become so successful that there are two locations in East Hampton alone!

One of East Hampton’s most infamous dining establishments is Nick and Toni’s flagship restaurant on Cedar Street. Nick and Toni’s opened in 1988 and have been providing Tuscan dining options in East Hampton ever since. The restaurant is equipped with a wood-burning oven and endless drink options that help elevate any dinner.

Something about spending the day at sea makes people crave fish and crab for dinner. If you are craving a meal from under the sea, Duryea’s Lobster Deck is the spot for you. This Montauk-based seafood restaurant has delicious lobster rolls and beautiful sea-ocean views.

Visit the Hamptons

The Hamptons is a great travel destination. They are still one of the few untouched locations where you can relax in the great outdoors, immerse yourself in art and history, and indulge in dining experiences without having to sacrifice quality.

Finding seclusion and tranquility in this beach paradise has proven time and time again to be one of the greatest ways to enjoy a summer in the Northeast, even though this coastal playground will always attract large crowds.

Once you’ve recovered from your Hamptons weekend, make sure to start preparing for your next trip because lodging and summer houses in this area tend to book up well in advance.

Contact our team to get started securing your Hamptons home for your next vacation.

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