Hamptons Gay Travel

wolfyy’s Hamptons gay guide to the best hotels and places stay, restaurants, beaches & local gay events.

The Gay Travel Experience: The Hamptons

The affluent group of towns and hamlets on southeastern Long Island are collectively known as “The Hamptons.” They bustle with tourists each summer, attracting locals from all over the New York City metro area. These posh seaside communities are famous for being a pinnacle of American wealth.

And by affluent, we’re talking about properties that are all worth at least a couple million dollars, if not within the typical range of 2 to 10 million.

Real estate in the Hamptons is some of the most expensive in America. Running into gay celebrities in the Hamptons is a common occurrence too, since many own summer homes out here.

Why are the Hamptons so popular? Well, the area offers seclusion, originally developed as an escape from bustling New York City life. These days, the Hamptons are a calmer, more upscale alternative than the notoriously extravagant Fire Island Pines.

Lush green space and historic charm can be found everywhere here in the Hamptons. A high-end art scene, swanky restaurants, and overall exclusivity continue to attract everyone looking for a serene getaway.

Gay travelers especially love visiting the Hamptons, notably the towns of East Hampton and Sag Harbor. Much of the Hamptons’ gay life concentrates in these areas. Every summer, and to a lesser extent year-round, LGBT life pervades these beautiful communities.

Remember that there are quite a few individual towns in the Hamptons. But the most sought-after and popular vacation towns are all between Southampton and Amagansett.

Where to Stay in the Hamptons

Finding the perfect place to stay in the Hamptons is a pretty big deal. It can sometimes be a bit of a challenge too, depending on your budget or what type of vacation rental you’re interested in. I’ll help you get oriented so you can enjoy the best trip possible.

Visitors generally stay in vacation rentals outside of the town centers. There are also some popular elegant cottage options within the main town areas, however, there simply are not as many options to choose from.

For gay travelers, the best Hamptons towns to visit are East Hampton and Sag Harbor. I’d definitely recommend staying somewhere near one of these towns.

High-end luxury Hamptons rentals curated by Plum Guide are the some of the most stunning and stylish options available on eastern Long Island. They’re definitely on the pricy side, but can be a great option for groups.

Easthampton Hotels & Vacation Rentals

Easthampton vacation rentals are gorgeous, many with beautiful backyard pools. I’d definitely start your search here.

Many gay travelers gather their friends to share larger home rentals, but there are also many cute cottages and small houses that are perfect for a romantic couple’s getaway.

The Maidstone

The Maidstone is one of the best hotels in East Hampton. It’s unbelievably charming and truly embodies the beautiful traditional style of the area.

The Maidstone has 16 rooms as well as 3 cottages, all with beautifully unique interior designs. Cottages even come with their own designated parking spaces!

The property was recently renovated in 2017, so you can expect modern conveniences during your stay in this 150+ year-old hotel.

Mill House Inn

Mill House Inn is another luxurious option. Right in the heart of East Hampton, staying in the Mill House Inn feels like a home away from home.

Choose among a number of carefully designed suites that come with everything from fireplaces to televisions in front of your bathtub! Plus, they offer personal assistants to help plan your days exploring everything the Hamptons have to offer.

Sag Harbor Hotels & Vacation Rentals

Downtown Sag Harbor is adorable. Endless high-end boutiques and restaurants line Main Street right through the middle of town. I absolutely love strolling through town and taking in the fresh summer air.

Vacation rentals in Pine Neck to the west of Sag Harbor Village are popular for their lush surroundings. Nestled into the woods, homes here enjoy total serenity with easy access to the water of Noyack Bay.

The American Hotel

The American Hotel in Sag Harbor’s quaint downtown is one of the most popular hotels with an old-town vibe. It’s one of the most popular places in town!

This historic hotel has been around since 1846! Completely restored in the 1970s, The American Hotel offers eight uniquely designed rooms and a delicious restaurant. Just driving past their outdoor seating will make you want to at least have lunch there!

Things to Do in the Hamptons

Life in the Hamptons is all about beaches, lounging in the summer sun. Vacationers love spending time enjoying nature and hanging by the pool in the backyards of their houses.

Many also love exploring local beaches, shopping, and attending local social events. Here are some of my recommended things to do in the Hamptons for gay travelers.

Two Mile Hollow Gay Beach

Two Mile Hollow is a must for first-time visitors. This is the prominent gay beach of the Hamptons, located between the towns of Amagansett and East Hampton.

It’s a lovely wide-open beachfront where you’ll be guaranteed to find a bunch of gay men and women every summer.

I also love Sammy’s Beach, which is a great spot to avoid crowds. It’s super quiet here!

Ocean Road Beach is another one of my favorites. It’s truly one of the most beautiful beaches around.

Arrive at the local gay beach in style with produce from my list of the best gay swimwear brands.

Visit Shelter Island

While it’s not the epicenter of gay life in the Hamptons, Shelter Island is still quite popular among gay visitors.

I recommend visiting Sunset Beach, a secluded stretch of sand anchored by the Sunset Beach Hotel and their chic restaurant & bar.

It’s easiest to visit Shelter Island if you’re staying in nearby Sag Harbor to the south. Charter a private boat that will sail you to Shelter Island for the afternoon. You’ll likely leave from the Sag Harbor Waterfront Marina.

Hamptons Gay Events

There are plenty of locally organized gay events in the Hamptons, from waterfront cocktail hours to tea dances. The Bay Street Theatre has traditionally hosted Music Mondays, which might be worth checking out.

View the local LGBT event schedule on the Hampton Gays website to see what’s planned during your visit.

Restaurants in the Hamptons

You can find upscale restaurants throughout all of the Hamptons’ neighborhoods, but there are a few in particular that gay travelers should know about!

Almond Hamptons

Almond Restaurant is an absolute staple among the Hamptons gay community. They’re a French restaurant located in Bridgehampton. Their food is divine, as are their cocktails.

Hugely popular are the Almond Hamptons gay nights. Every Friday during the summer season, the LGBT crowd pours into Almond. It’s definitely “the place” to be seen for LGBT regulars (or visitors)!

Don’t expect any drag queens or a show, but dress your best and get ready to experience incredible energy.

Lobster Roll & Clam Bar

Anyone who’s familiar with the Hamptons will tell you that these two restaurants are a must!

Lobster Roll and Clam Bar are both no-frills seafood spots in Amagansett that always draw a crowd. They’re both on Montauk Highway in Amagansett, only a minute apart from one another.

I love Clam Bar specifically for their relaxing outdoor seating. Lobster Roll has both indoor and outdoor seating. I recommend heading to one of these local lunch spots on a day when you’re sure there’s no chance of rain.

Cittanuova

Cittanuova is a great Italian restaurant for lunch or dinner with the option of outdoor seating. I loved their tables under the terrace in the back. Directly in the center of Easthampton town, Cittanuova is also popular for its evening bar scene.

Lots of people stop by for evening cocktails. If you’re calling ahead, I’d try to make sure you can get a table that’s either outside or somewhere near the open-front section. It’s much better than booths in the back of the restaurant.

More Hamptons Restaurants

I absolutely loved DOPO La Spiaggia, an Italian restaurant in East Hampton. The service and food were delightful, and the plate presentation was wonderful. They also have a second location in Sag Harbor. Especially during the summer season, try to make a reservation well in advance.

Craving some steak or seafood with classic American sides? Head over to Bobby Van’s Steakhouse in Bridgehampton. You’re guaranteed to enjoy a mouth-watering meal. Bobby Van’s also has reasonably priced drinks for happy hour. Cocktails are only nine dollars!

Last but not least Bell & Anchor is great for dinner. Their dimly lit space was so cozy and inviting. Bell & Anchor is popular for its raw bar and rich, savory entrées.

Hamptons Gay Travel Tips

Dress Your Best

Make sure to bring your best beachy summer clothes. Everyone in the Hamptons dresses quite elegantly.

Think boat shoes, seersucker shirts, pastel shorts, and sundresses. Locals and vacationers love embracing the tranquil summer Hampton vibes. For some easy inspiration, check out wolfyy’s gay fashion idea list on Amazon.

How to Get to the Hamptons

The majority of people drive to the Hamptons, as most people are coming from New York City or elsewhere on Long Island. If you’re planning on visiting without a car though, there are a few other options.

Hampton Jitney buses operate between Manhattan and the Hamptons. The journey takes between two and three hours.

No matter what method of ground transport you use though, carefully plan around traffic anytime between May and September. Traffic congestion can be pretty severe, especially on Fridays during summer. So, it’s best to plan to avoid these busy times if possible.

The Long Island Rail Road is another popular option to quickly get out to the Hamptons. During the summer seasons, express trains run directly from New York City to all the towns out on Eastern Long Island.

While out of most of our price ranges, it’s worth mentioning the (pretty awesome) option of getting to the Hamptons via helicopter.

Affluent locals use Blade, a helicopter service that offers shared rides and private charters directly to the Hamptons from Midtown Manhattan.

Hamptons Gay Nightlife

Out here in the Hamptons, there aren’t any traditional gay bars. Instead, LGBT tourists here congregate in a few gay-friendly favorite restaurants throughout the summer, like the previously mentioned Almond Restaurant.

If you’re looking for drag queens and rowdy gay bars, you might be better off checking out Fire Island Pines and Cherry Grove, the two magical gay beach communities further west on Long Island that locals love.