long island view from the lighthouse

The view from the top of Fire Island lighthouse

Beach

Long Island is famous for its beaches, especially on the Atlantic Ocean-facing South Shore, where you’ll find the Hamptons, Fire Island, and Long Beach. These sandy beaches and ocean waves are a contrast to the North Shore, which is made up of pebbled coast and calmer waters, ideal for enjoying canoeing and kayaking. Looking out over the Long Island Sound on a clear day, you can spot the outline of Connecticut. Whichever your preference, Long Island beaches mean old-school summer holidays vibes, with lighthouses, ice creams on the beach and strolling along the waterfront.

Our picks for beachside stop offs are:

long island lighthouse

Fire Island lighthouse

Sound View, Greenport – a quiet waterfront retreat

If your idea of the perfect beach getaway is a ‘quaint weatherboard beach house on a summer holiday’ vibe, then head to Sound View in Greenport. This delightful little hidden gem looks unassuming from the outside but once you head through those doors, you’re transported into your own waterfront retreat. Grab breakfast from the continental buffet and eat overlooking the water, or take in the same view at nighttime with dinner and a drink. The whole place is beautifully designed and furnished with a distinct nautical feel.

The rooms don’t disappoint either. Beautiful furnishings across a bedroom, bathroom, living area and small convenient kitchen, plus lovely French doors that open out onto a big balcony where you can enjoy a stunning view over the Long Island Sound.

long island the hamptons

A beachfront room terrace at Gurney’s, Montauk

Sag Harbour – the pretty seaside town

Head here for a tight-knit community feel, and great shopping and food, with a very glam but still family-friendly atmosphere; it’s the Hamptons, but maybe not quite as you’d expect it. There’s a beautiful high street stretching down to the bay and a leisurely stroll along Bay Street will have you on Havens Beach for a play in the sand. We recommend going for a stroll through the tree-lined streets with an ice cream (or delicious hot chocolate in the winter months) and simply taking in the pretty town. There are some huge, beautiful houses and old buildings, and an interesting whaling museum that showcases the marine history of the town.

Montauk – glam in the Hamptons

If you’re after the full glitz and glam of Long Island, and to summer like a celebrity, Gurney’s Montauk Resort & Seawater Spa is the true Hamptons experience. Montauk is known for its chilled, surfer atmosphere so it’s no surprise that families across New York State come here for their beach break. During the summer months, this place is packed to the rafters with holidaymakers enjoying the vast outdoor spaces and private beach with 2,000-feet of pristine sand, reserved for only Gurney’s guests.

Their fitness and spa facilities are renown across Long Island and New York City so you can take a dip in the salt water pool with the kids, or have time by yourself whilst the little ones are in kids club.

Fire Island – the car free island getaway

Fire Island is a popular holiday spot, especially during the summer months, but it’s pretty all year round. Spend a lazy morning walking along the beach and take a trip to the top of the lighthouse for amazing views and see if you can see the faint outline of the Manhattan skyline on a clear day. It’s worth all 192 steps.


Countryside

Long Island has a unique landscape, not least because it’s a huge 118 miles long but only 28 miles wide at its widest point. This means more coastline than you know what to do with, but also so much greenery and countryside charm that you can take a family holiday that has a bit of everything. With over 100 state parks, county parks, and nature reserves, you’re never short of a place for a lovely walk spotting wildlife and taking in the views. Along
your way, get into the country lifestyle at some of these stop offs:

Sep’s Farm, North Fork – family run farm for a day in the dirt

Serving the best in fresh to the North Fork community for over 60 years, the family-run Sep’s Farm handpicks fruit and vegetables daily. You’ll get an insight into the North Fork community where local families come to buy their fresh produce and make a day of picking pumpkins with the kids. Treat yourself to some homemade mustard, pickles and sauces to take a piece of the countryside with you.

Oheka Castle – absolute decadence

A long driveway to a grand estate, perfectly manicured gardens, dazzling chandeliers and soaring towers. Think The Great Gatsby, total extravagance in total luxury. Oheka Castle is a piece of American history, built and run by the intriguing and fascinating Otto Kahn, who held parties for New York socialites and was good friends with Charlie Chaplin. Old school glamour at its finest.

sweet mamas stony brook long island

Sweet Mama’s fried chick and waffles

long island countryside

Stony Brook’s historic post office

Wine tasting in Greenport – a stroll through the vineyards

Whether you’re a regular connoisseur of fine wines or not, a stroll through the vineyards taking in the country views is a lovely way to spend an afternoon. If you do enjoy wine though, Greenport is a special area for winemaking in that it grows multiple varietals that you’d rarely find together anywhere else. You’ll find the winemakers and sommeliers here very approachable and knowledgeable if you’d like a recommendation. Kontokosta Winery is a prime example; sitting on 62-acres, this tasting room and winery sits on the Long Island Sound waterfront, giving amazing views and plenty of space for the kids to play and run.

Stony Brook Village – food, shopping and strolling around 

This idyllic spot on the North Shore is every part the all-American, picture-perfect town you’ve seen in countless movies, with its tree-lined streets and family-family owned businesses, including a delightful British tearoom and an incredible 50s American food spot called Sweet Mama’s, where the giant waffles and breakfast cocktails are the best way to start the day before you head to Avalon Park for walking and wildlife spotting with the whole family.

Brew Cheese is a must-do for local and carefully selected cheeses and beers, whilst the whole family can indulge, in Chocolate Works. Dip your own strawberries and marshmallows in decadent liquid chocolate, treat yourself to a box of handmade delights, and marvel at the edible works of art.


City

Brooklyn

If you think of Brooklyn, you think of New York City. However, despite its proximity to it’s very famous neighbour, Manhattan, Brooklyn is technically on Long Island and a great inclusion into your Long Island trip. Think traditional delis, fresh bagels, cosy nooks in busy bars, and an underground music and arts scene. Trendy Williamsburg is a beautiful family spot to visit, especially for Smorgasburg open-air food market, a sprawling waterfront space where the best food vendors congregate to sell everything from home-smoked meats to vegan burgers and sweet treats.

New York City 

Long Island is the beachfront backyard of New York City, making it the ideal ‘city break with a country escape’ for UK families. After all of the city excitement with the family in Manhattan, join the locals heading east for their own family holidays, slipping into a slower pace of life.

long island williamsburg bridge

Willamsburg Bridge, NY

The lowdown: Long Island

Getting there

British Airways fly direct from London Heathrow to JFK airport, from £348pp return

Flight time is 8 hours

Getting around

The easiest option is to drive so that you can stop off whenever you like. You could fly into one of the three airports on the west end of Long Island then hire a care and drive right to the tip of the North and South Forks and enjoy everything the island has to offer on the way.

There are buses and trains, operated by the LIRR (Long Island Rail Road) via the MTA (Metropolitan Transportation Authority), which might be a good idea if you’re staying in a particular area or are going to The Hamptons in the middle of peak season as the traffic is notoriously busy at those times. A 7-day MetroCard is $32.00.

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