The Hamptons. New York’s exclusive seaside getaway, where the rich and famous retreat to lap up the sun on picturesque, golden beaches.
Apparently.
I wouldn’t actually know. When I had the chance to play out my high-society fantasies in the Hamptons in late June, the weather was, quite frankly, miserable. The only beaches I glimpsed were moody grey, cloaked by rain and heavy mist. It wasn’t at all the idyllic getaway that Kortney and Khloe take the Hamptons had promised.
But hey, you can’t win them all – sometimes the weather just doesn’t turn it on. So while there may have been some sulking on my part to begin with, the conditions did provide the incentive to venture inland and discover the Hamptons’ rural charm.
Whether it was meandering through charming historic towns, sipping wine amongst lush vineyards, or dining out on the freshest seafood, it turns out there was plenty to enjoy in the Hamptons that didn’t involve a beach chair. Here’s how we spent our time in a very wet Hamptons – if you’re looking for ‘best beaches in the Hamptons’, this post isn’t for you!
Where we stayed
The Hamptons are a stretch of towns and villages along the South Fork (at the eastern end) of New York’s Long Island. We stayed in Montauk, the furthest village away from Manhattan and the last stop before the Atlantic Ocean. The boho-chic village has always been a popular spot for surfers and artists, making it more chilled than its neighbours – but it’s fast gaining a reputation as the Hamptons new hot spot. As a result, there’s a thriving restaurant and bar scene.
The main reason we chose Montauk was so we could spend our days at Gurney’s Beach Club, an insta-perfect private beach decked out with lavish day beds. The Beach Club is part of Gurney’s Montauk Resort and Seawater Spa hotel, a 5-star hotel that comes at a hefty price tag well out of my budget.
Instead, we stayed at their sister property, Gurney’s Star Island Resort & Marina, located nearby on Lake Montauk. Star Island is (marginally) more affordable, particularly on weekdays when we stayed. And while it didn’t feel as opulent as the Montauk Resort, I loved its laid-back vibe and nautical charm. And there’s a free shuttle to the beach club, should the weather play nice.
Gurney’s Star Island Resort & Marina, 32 Star Island Road, Montauk, NY 11954
The view from my hotel room the night we arrived. It was to be the last time we saw sun for many days…
Where we ate
Seafood lovers will love the Hamptons, where overdosing on lobster rolls and clam chowder is a very real risk.
To nibble on crustaceans in a picture-perfect location, look no further that Duryea’s Lobster Deck. Sitting on the deck overlooking Fort Pond Bay was the perfect spot for kicking back with a bottle of rosé and watching the afternoon roll by (until that pesky rain came back).
While it’s mostly al fresco, there’s indoor seating should the weather turn nasty. They don’t take reservations, so best to get there early in the height of summer.
Duryea’s Lobster Deck, 65 Tuthill Rd, Montauk, NY 11954, USA
The Crow’s Nest was the most atmospheric restaurant we found in Montauk. Outside, the spacious lawn is lit by hanging lights that guide you down to Lake Montauk, while the rustic, wood-panelled interior is warm and inviting. The Mediterranean-inspired menu is seafood heavy as you’d expect given the area, although meat-eaters and vegetarians won’t leave hungry.
They don’t take reservations, but with a lakeside bar complete with firepits, having to wait for a table is almost preferable. (But still get their early – the wait list fills up quickly in peak times.) My only gripe was that as friendly as the service was, they did rush us through the meal at a galloping pace.
The Crow’s Next, 4 Old West. Lake Drive, Montauk
The Crow’s Nest lakeside bar
For a more upscale affair, we chose Scarpetta Beach, an outpost of the well-known Manhattan Italian restaurant. Scarpetta has found its Hamptons home in Montauk’s Gurney’s Resort & Spa hotel.
The softly lit, open dining room oozes sophistication, and the food was delicious, with plenty of fresh local seafood on the menu. It also has an elevated deck offering ocean views, from which I’m reliably told you can take in the sunset with a cocktail when the sun has actually made an appearance.
Scarpetta Beach, 290 Old Montauk Hwy, Montauk (within the Gurney’s Resort & Spa hotel)
For something more low-key, try the The Lobster Roll (simply known as ‘Lunch’ to the locals due to its large sign overhead). It looks little more than a roadside shack, but the expansive seafood menu with no-frills outdoor seating makes it a bona fide crowd-pleaser.
The Lobster Roll, 1980 Montauk Highway, Amagansett
What we did
Exploring villages (and window shopping)
East Hampton is home to many a business tycoon and celebrity, so of course we couldn’t help but stop in for a sticky beak. Shopping along its main street provides a good of indication how the other half live, with many of the stores being designer boutiques. It all left us pondering, ‘what exactly do the locals get when they say “I’m just popping out to the shops.”?’
But even if you’re not in the market for a designer outfit, there’s still plenty to enjoy about East Hampton. It was by far the grandest of the villages, with decadent timber-fronted colonial properties perched atop perfectly manicured lawns. It’s also incredibly charming, with vibrant green gardens, quaint windmills and a small, peaceful lake. It’s well worth stopping in for a stroll, and the property porn.
Sag Harbor was another of my favourites. Once an old whaling centre, today the pretty village on the north side of the South Fork is like a time capsule; its perfectly preserved 18th and 19th Century architecture transporting you back to the America of yesteryear. (Nowhere will you feel this more than in the historic The American Hotel with its old world feel and classic cocktails.)
While Sag Harbor has its share of designer boutiques and upscale restaurants, (furniture and homeware lovers will be in heaven), it still feels very accessible. Friends meet at buzzing cafes, people are out shopping in local stores, and kids race to get that ice cream their parents promised them. You can’t help but feel Sag Harbour is a little more grounded than some of its Hamptons siblings.
MONC XIII – one of Sag Harbor’s many designer homeware shops
Wine tasting
Something I did not know about the Hamptons, and Long Island more generally, is that they have a burgeoning wine industry. I was pleasantly surprised by the wine that was on offer too, particularly the rosé.
We started at Channing Daughters, a small winery with scenic vineyards decorated with wood sculptures by owner/sculptor Walter Channing. A tasting here is $20 per person and no appointment is needed for groups less than six. It’s also much quieter than nearby Wolffer Estate, making it a tranquil oasis to unwind with a glass and take in the fresh Hamptons air.
Channing Daughters, 1927 Scuttle Hole Rd, Bridgehampton (open daily, 11:00am-5:00pm)
From there we moved on to Wolffer Estate, a much bigger and busier winery. (So popular it has several establishments across the Hamptons, including The Wine Stand, just around the corner on Montauk Highway.)
Where Channing Daughters was a modest affair, Wolffer Estate is much slicker, with a large tasting room and terrace from which to sample the wine and snack on local produce. Officially, reservations are required for a sit-down tasting – however we didn’t have a reservation so that might just be at peak times.
Wolffer Estate, 39 Sagg Road, Sagaponack (open daily, 11:00am-8:00pm)
Wolffer Estate tasting room
Beer tasting
What better to do after a wine tasting than move onto beer? Ok, so perhaps we did that the wrong way around. Nonetheless, it was great to try the local brew at Montauk Brewing Company.
What started as a basement brewing operation in 2012 has grown into a celebrated brand. Even mid-week this little brewery was buzzing. The tasting room is small, but there’s a beer garden that would be the place to be in more accommodating weather. You can purchase tasting flights or beer by the pint. My favourite was the Watermelon Session Ale, which may sound revolting but was surprisingly refreshing!
Montauk Brewing Company, 62 South Erie Avenue, Montauk (open daily, 12:00pm-8:00pm)
Work out
We went to Barry’s Bootcamp, which has not one, but three locations across the Hamptons (although truth be told, despite the hefty price tag, I felt like I was working out in a barn). If Barry’s isn’t your thing, you’ll find many other well-known studios in the area, including Soul Cycle and New York Pilates.
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Of course, the other thing to do in the Hamptons would be to take advantage of the abundance of world-class beaches along its shores. But those I’ll have to leave up to you to discover on your own. Sigh.
Quick tips when visiting the Hamptons
The Hamptons are around three hours from New York City, traffic dependant. If you don’t have access to a car, there are several public transport options available:
– Hampton Jitney departs Manhattan regularly (and has an airport connection stop a short taxi ride away from JFK and LaGuardia airports). Off-peak fares are $35 one way or $30 if booked online.
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| A car is a must have if you’re planning on doing any sort of exploring. We rented a car and drove from Manhattan, but there are plenty of car rental options in the Hamptons themselves. |
If you’re looking for more beachside destination ideas, check out my posts on Mykonos, Portofino or Skiathos.