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A tall white lifeguard seat sits on golden sand to the left of the frame facing the sea. Blue sky above. There are some people sitting on the beach in front of the chair

Enjoy Impressive Long Island Beaches, Towns And Vineyards On A Road Trip Loop

7 August 202515 min readAdd comment

Long Island is often thought of as a summer playground for wealthy urbanites from New York and, being so close to the city, it’s easy to understand why this might have become the case. Today, it’s not just New Yorkers who flood here ‘to summer’ on beautiful Long Island beaches and hang out in the smart Hamptons and dreamy vineyards. We passed through on our short road trip loop and would return in a heartbeat. Read on to find out why…

Table of Contents

Where is Long Island?

Long Island in New York state stretches east from New York City for around 190 km (120 miles), with John F. Kennedy Airport to the west and Montauk to the east, the New York Sound running long its northern edge, Block Island Sound to the right and Atlantic Ocean on its southern side.

Long Island is therefore perfectly accessible from John F. Kennedy Airport, and from a road trip perspective, you can be out of the airport and straight onto the Long Island roads without having to navigate New York City. Check out my blog about Travel Planning a Road Trip from Long Island for more information about the roads (and ferry crossings).

There are many beautiful sandy Long Island beaches very close to Manhattan, including Jones Beach which is only 40 miles from Midtown Manhattan, making it Long Island’s most famous and accessible stretch of sand.

The Hamptons

The Hamptons is a collection of towns and villages across the South fork of Long Island, including Westhampton (the original Hampton), Southampton, East Hampton, Amagansett, Montauk, Sag Harbor** and several more. **Using American spellings for place names – Sag Harbor / Montauk Harbor

As a guide, the drive from JFK Airport to Montauk at the furthest point east takes around 2 hours 50 minutes, or 1 hour 50 minutes to Westhampton.

View of the body of a mannequin in shop window. It is wearing a black t-shirt with a white graphic saying 'The Hamptons' across the front. Wearing black and white striped shorts and has a black and white striped top draped over shoulders. Green plant to the right
Hamptons merch

When to go to the Hamptons?

High Season for this the Hamptons is from the end of May until the start of September. During this time, everything will be open and ready for beach life with summer activities on the Long Island beaches.

Many of the Long Island beaches are private but that said, there are still plenty of stunning public beaches to explore. Note – in some areas you may require beach passes (or parking permits) for High Season visits, but your accommodation may be able to help you with these.

We were travelling in the third week of July and had beautiful weather on all but one morning, when there was a thunderstorm which passed by early afternoon.

Southampton, a good base in the Hamptons

As we were exploring the area on a road trip, we weren’t too bothered about booking somewhere with beach access, so settled on a guest house in Southampton through Booking.com. Whilst its location was good, I wouldn’t particularly recommend the guest house due to its creaky floorboards, noisy adjoining restaurant, and surly staff.

However, I spotted the nearby 1708 House which, from its website, looked like a much better option right in the town centre. This was also available on Booking.com and includes Southampton beach passes in their prices. I’ve made a mental note of this one, should there be a next time!

A cream clapboard building stands across the frame from the left. It has a verandah with columns around a wooden front door. Rocking chairs on the verandah. Starts and Stripes over the front door. Trees to the right
1708 Guest House, Southampton

What to expect in Southampton

Southampton is a well-heeled town with smart shops and buzzing restaurants set out around a crossroads, keeping everything close together. Whilst the town has a relatively slow pace of life, you can find:

  • History – note the old street sign showing the town’s age, year 1648.
  • Cute buildings – the Pelletreu Silver Shop, a tiny Dutch barn made in 1688, once the workshop of a Silversmith from 1726-1810. Also note the pretty white clapboard buildings and churches, such as, the Methodist and First Presbyterian Churches.
  • Compact shopping – there is a nice mix of brand shopping such as J Crew and Ralph Lauren, plus lots of independent shops and boutiques, all in a couple of small streets.
  • Gourmet food markets and delis – Citarella is a gourmet market (posh supermarket) selling things which are perfect for picnics, plus hot options and lots of snacks. I’ve never come across as many organic delis in one square mile before!
  • Wellness outlets – for beauty and spa treatments, including Hampton Hot Yoga.
  • Beautiful beaches – an array of golden sandy beaches (see below).
Old blue signpost which says 'Ye towne Street Opened 1648'. Tall trees with green leaves in the background.
Ye Olde Southampton!

Although we didn’t eat out much in Southampton due to our schedule, the restaurants looked busy, such as 75 Main (apparently a celeb haunt) and Argent. The Golden Pear was good picking up coffees, pastries, bagels, and Hampton-themed sandwiches.  After paying, you can pour your own coffee from the hot plates on the counter which feels very American. 

White wooden clapboard building with a grey-green doorway to the left handsome. It says 'Le Shop' in black letters on white sign over the doorway. Whicker basket and bags on display around the doorway.
The boutique vibe

Buddhaberrry is a great frozen yoghurt outlet when you can ‘try before you buy’ from a large assortment of flavours before adding from a multitude of toppings.

We enjoyed Happy Hour cocktails and beers at the Southampton Publick House one night, sitting in the outdoor patio with one eye on the baseball on the TV screens and one eye on the comings and goings around us.

Southampton looked pretty at night, lit up by fairy lights, and with fireflies visible in the grassy areas!

Street scene at dusk. The street is lined with clapboard shops illuminated by fairy lights and with flowers around the doors. The shop closest to the camera says 'Toplaire Flower Shop' and has a giant purple elephant peering around the far side of the shop.
Southampton at dusk

Chill on Cooper’s Beach

My pre-trip research of the Long Island beaches suggested that Cooper’s Beach was “one of the best public beaches” in the Hamptons, so we bought sushi from Citarella and headed over to the beach for 6pm by which time parking was free and permits weren’t required.

Cooper’s Beach is a wide stretch of soft, golden sand with Atlantic rollers in front and huge houses backing onto the sand, with lifeguards on duty during the day (see featured photo).

During the summer season, there’s a programme of live music on the beach, so we were able to chill out on the beach along with locals and holiday makers, sharing wine, chatting, and listening to the music. Whilst jet lag cut our evening short, we still felt that we had experienced a slice of real Hamptons life in the fading sunlight of a summer’s evening.

Beach scene of a gathering of people sitting in multicoloured deckchairs in lines across the sand with a stage on the horizon. Blue sky above. A man in blue shirt sits in the foreground on a green towel facing away from the camera
A white stage which looks like a trailer with open sides in the bottom left of the frame. There is a band on the stage playing instruments including saxophone, guitar and double bass. Stars and Stripes flag being the band. Blue sky and line of parked cars to the right
Let the music play on Cooper's Beach!

If rubber-necking enormous houses is your thing, then you can check out the whoppers on Gin Lane in Southampton, home to some of the most expensive pads on Long Island (reportedly up to $150 million – fact check required). We took a detour down Billionaire’s Lane (Meadow Lane) to ogle at the multi-million-dollar homes and spotted a deer strolling casually down one of the driveways – welcome to the Hamptons!

Explore more of the Hamptons

Our strategy was to drive to the furthest point and work our way back to Southampton, so we headed over to Montauk State Park at the eastern most point (‘the End’), where Block Island Sound meets the Atlantic Ocean, just over one hours’ drive from Southampton.

Montauk ('the end')

Montauk Point State Parks

There are six state parks in Montauk, including: Montauk Point State Park, Camp Hero, Montauk Downs, Hither Hills, Shadmoor, and Napeague, all offering places to explore and go for walks in the wild landscape. Cape Hero has an historic military installation to see as well as forest, beaches, and fabulous ocean views.

Montauk Point Lighthouse

The Montauk Point Lighthouse sits next to Montauk Point State Park at ‘the End’ and is the oldest lighthouse in New York state, commissioned by President George Washington in 1792. Before the English settlers and development of the lighthouse, Algonquin-speaking Montaukett Indians would light watch fires on the cliffs here to guide their canoes home.

Looking up at the tower of a white and red striped lighthouse. Glass light room at the top. Red roofs a the bottom on either side. There is a Stars and Stripes flag flying at the bottom left. Cloudy sky behind.
Montauk Point Lighthouse at 'the End'

There’s a large car park at the lighthouse which opens at 10.30am until 4.30pm daily (longer on Sundays). It costs $15 entry per person to access the lighthouse and a small museum.

Enter the lighthouse keeper’s house and explore the exhibits of the ground floor museum, which explain the history and significance of this historic lighthouse. On the displays, look out for:

  • The documents written and signed by George Washington and Thomas Jefferson.  
  • The story of Princess Pocahontas Pharoah, the daughter to David and Maria Pharoah, King and Queen of the Montauk tribe.  Princess Pocahontas was known for making medicines from herbs and shrubs. 
  • The photo of Frank Mundus, a local shark fisherman said to be the inspiration for the character Quint in the film JAWS, filmed in nearby Martha’s Vineyard. 

Then climb the 137 steps to the watch deck of this still working lighthouse to see the large lens at the top and views over the water, staying alert for signs of Abigail the ghost of the lighthouse.

View from the top of a building, possibly a lighthouse, looking down on a cluster of white buildings with red roofs and a Stars and Stripes flag to the bottom right. Beyond is a beach and coast line to the left, trees to the right with a road curving through. Pale blue sky above
Close up of a lighthouse lens mounted on a brass fitting inside the glass windows
The huge lens still lighting the cliffs of Montauk State Park

Back at ground level, take a moment to remember those Lost at Sea at the memorial on the cliff edge.

Montauk Harbor

Head west towards Montauk before taking the turning towards Montauk Downs State Park and Montauk Harbor. Wander around this nautical area, home to the largest fishing fleet in New England and Gosman’s Fish Market.

If it’s lunchtime and you’re hungry, pick up a Lobster Roll or Lobster Bisque from Gosman’s Clam Bar and sit at one of the outdoor tables watching the boats coming and going from Lake Montauk and Block Island Sound. Watch out for the greedy seagulls!

Close up of a seagull standing on a wooden post in the centre of the frame. It has a yellow beak and is looking slightly to the left hand side. Beach, water and beach buildings blurred in the background
Looking for a lobster roll lunch...

If you want to explore more of the wonderful Long Island beaches then there are plenty around Montauk, including Ditch Plains Beach (with surfing opportunities) and family friendly Gin Beach.

We didn’t stop in Montauk Village choosing instead deciding to continue to East Hampton. If you didn’t eat in Montauk Harbor, then you might consider stopping at LUNCH Lobster Roll in Amagansett on the way, known for its lobster rolls made of 100% pure cold-water lobster. Look out for local resident Gwyneth Paltrow whilst in Amagansett!

A hand holds a brioche or bread bun up to the camera. It is filled with a chopped salad and what looks like lobster (lobster roll). Behind the roll is a body of water with house, grass and beach on the horizon
A very tasty lobster roll in brioche bun, Montauk

East Hampton

Shop till you drop in East Hampton

On the way in and out of East Hampton you pass the Hook Windmill, a wonderful old windmill built in 1806 which operated for 100 years turning grain into flour and feed – one of 11 windmills on Long Island.

The town of East Hampton has the glitziest shops, including luxury brands such as Luis Vuitton, Chanel, and Prada. It also seemed to have the most traffic and impatient drivers honking their horns!

Looking up at a curved white shop front with white sunshade over the front door. It says Prada in black letters. Trees to the right hand side
Shop front - white arched doorway with two large windows filled with books either side. A navy blue sign says Book Hampton over the doorway.
Book-tastic!

We enjoyed some window shopping in this exclusive town, browsing in the book shop, before picking up snacks from Citarellas (when something works…) before heading off to the Longhouse Reserve in search of some solitude.

Visit Longhouse Reserve, a Hamptons hidden gem

The Longhouse Reserve sculpture park is a don’t miss destination if you have time to wander through the 16 acres of pretty gardens and trees. It’s the home of late textile artist Jack Lenor Larsen and the gardens are full of sculptures by well-known artists, such as Yoko Ono, Wilem de Kooning, Ai Wei Wei, and Daniel Arsham, although the pieces on display change periodically.

When it’s hot in the Summer, this is the perfect place to seek sanctuary under the shade of the trees. I loved Dale Chihuly’s Cobalt Reeds by the lake, having been a fan of his art since we visited his glass museum in Seattle. I also enjoyed spotting the tame rabbits bobbing around the grounds.

A sculpture comprising of multiple towers of square grey bricks, all different heights in a cluster, stands to the centre left of the photo. Green trees behind
Silver sculpture like a geometric totem pole stands to the front right of frame with a walkway to its left. Three females are walking away from the camera in summer dresses. Surrounded by trees
View of a garden with lawn in front and green trees in the background. Across the front are 4 multicoloured low chairs - two pink, one yellow and one green. A lady in green dress and straw sunhat sits in the middle pink hair stretching arms to side of heads
The peaceful sanctuary of Longhouse Reserve

If you like art and have the time, you can also visit the Pollack-Krasner House – former home and studio of Jackson Pollock and Lee Krasner which is nearby.

Sag Harbor on the South Fork

Sag Harbor is about 30 minutes’ drive northeast of Southampton and was my favourite place in the Hamptons (despite its extensive whaling history). It was once home to Algonquin Indians which linked with a previous canoeing adventure in Algonquin Park, Ontario, Canada.

First, we explored the windmill standing at the entrance to Long Wharf filled with lovely boats of various shapes and sizes. The original windmill was built in 1760 to be used in the processing of whale oil during the 19th century. The one you see today is a replica, erected as an historic monument to the whaling industry which once made Sag Harbor a bustling, commercial port town. We gave the Whaling Museum a miss…

The top of a wooden windmill appears in bottom right of the frame. It's four wooden sails fill the rest of the frame against a blue and white cloud sky
Sag Harbor Windmill, Long Island

Despite its small size, Sag Harbor has both a small Art Deco cinema and the Bay Street Theatre, along with a lively main street of shops, antique stores, and restaurants. The town also has a BuddhaBerry Frozen Yoghurt shop – noted!

Sign for a shop called BuddhaBerry appears in coral colour on a white sign in bottom right of the frame. Large columned entranceway to the left. White clapboard building behind. Some trees and shrubs surround the shot
The front of a two storey brick building fills the frame. It has white window and door frames, and pink and white decoration. There are pink roses around the sign over the front door saying 'LoveShackFancy' on it . Dresses on show in the windows.
Pretty shops in Sag Harbor

If you have an opportunity to stay over for a night then consider the upmarket American Hotel, or alternatively book in for a meal (reservations generally required).

White plaster wall with red Art Deco letters saying 'Sag Harbor' sitting on striped platforms. trees and brick building to the right
Lovely Art Deco cinema, Sag Harbor

John Steinbeck's House

John and Elaine Steinbeck lived in Sag Harbor from 1955 until his death in 1968, and is now open for visits.  He wrote The Winter of Our Discontent during his time living at the house. 

When we visited I was reading Travels with Charley by Steinbeck which follows his road trip in search of the real America.  Charley is his French Poodle who dog lovers with adore.  His journey sets out from Sag Harbor and takes the same ferry routes (detailed below) across to New London, Connecticut.  I didn’t realise we would be following in his footsteps when planning our route!

Use the ferries between the North and South Forks

Take the South Ferry to Shelter Island for lunch

As explained in my blog Travel Planning a Long Island Road Trip, you can take a small car ferry across the water to Shelter Island, only 5 minutes away.

View from a car ferry across the water to a second small white car ferry making its way across the water. Blue sky with cloud above. Dark coloured car along the bottom of the frame
On the South Ferry to Shelter Island

We took the ferry across and enjoyed a lovely lunch at SALT Waterfront Bar and Grill on the deck overlooking a small marina with the Peconic Bay in the background.

View of a marina with small boats moored along the front edge and back edge of the harbour. A beige sun parasol appears to the right hand side of the frame. Tree on the far side of the harbour with blue sky above
View from SALT Waterfront Bar

Take the North Ferry to Greenport

After lunch, and potentially a snooze on Crescent Beach on the northwest of Shelter Island (more pebbly than most of the Long Island beaches), you can then catch the North Ferry to Greenport on the north fork of Long Island.

View from a golden sandy beach to a lake with a small sailing boat in the middle. Row of trees along the horizon. Pale blue
Crescent beach, Shelter Island

North fork vineyards

We decided to stay for a night in Greenport to be well positioned to visit some of the many vineyards in this area, including:

  • Croteaux – a French styled (Provence) tasting garden and winery specialising in Rosé wines.  It’s open from 11am to 6pm and you can pop in, no reservations required, to sample a flight of rosé whilst sitting in an idyllic garden next to the vines.
  • McCall Wines – we booked a special Burger and Wine Night at McCalls and spent a wonderful couple of hours sitting in a garden lit by fairy lights outside a barn, sampling red wines.  You should book a slot for this special event as all tables were full for the duration of our visit.  I loved watching groups of friends and multi-generational families chatting and eating as the sun started to set.

Looking through the branches of trees towards a building with open turquoise wooden shutters and lavender growing on the window ledge. Three wooden Adirondack chairs sit along the bottom of the the frame
A metal drinks holder sits on a metal table outside on a gravel floor. In the drinks holder are a couple of glasses of wine (sparkling). To the right is a glass of pink liquid
Flight of rosé wine at La Croteaux Vineyard

Note 1 – most accommodation options in the north fork seemed to have minimum night stays and I concluded that it is a very popular spot, not just with New Yorkers and locals, but also with visitors from New England coming via the Connecticut ferry. It would make the perfect weekend getaway from across the water!

A row of green wines reaches from the bottom left to the middle right of the frame. No visible grapes. Row of trees behind and blue sky above
Vines at McCalls Wines

Note 2 – there are also vineyards in the South fork including: Duck Walk Vineyard, Wolffer Estate Vineyard, and the Channing Draught Winery. If we hadn’t been intending to catch the ferry to Connecticut from the north fork of Long Island, then we might have stayed longer in the South fork and explored the vineyards there.

A silver caravan sits to the middle left of the frame. To the right is a picnic table surrounded by 7 people - family or friends. Light bulb string above and green grass in front.
Two glasses of wine sit on a wooden table outside in front of a green lawn and picnic tables full of people. The glass on the left has red wine in it and the glass to the right has white wine in it.
Burger night at McCalls Wines

Final thoughts….

Long Island made for an enjoyable destination and one which I would be happy to return to.

I’m not sure we found the heart of Montauk and so I would be keen to try again there, but Sag Harbor was a destination of choice.

The whole area was spotless, easy to drive around and very pretty – tick!

There’s no escaping the fact that the area is pricey, even if you’re only in town for a couple of days but sharing food (as portion sizes so generous) and staying in guest houses helped to keep our costs down a bit. Our ‘summer playground’ was the public beach rather than the private beach clubs, but that’s fine with us. Just happy to be in town!

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