There is a rule all blossoming New Yorkers are meant to abide by: the first order of business when arriving in the city (next to survival and mentally adjusting to the $7 for a coffee standard) is to befriend someone with a house in The Hamptons. While I see the merit in this task, my trip to Long Island’s most famed shore only ignited more personal real estate goals, rather than relying on those of others; because trust me, this breezy escape from the city is a completely necessary one to the New Yorker lifestyle.
Thanks to recent Meg Ryan movie and Sex and the City marathons, I needed to feel spring in a rush – even if it meant embarking on a road-trip outside the city to make it a reality. D and I took our wintery frustrations in the backseat of our canary yellow Ford Mustang rental and took the long route (Montauk highway) to Southampton…I was surprised at how vast this elite strip of these cozy beachside villages actually was. In my first Hamptons guide, I want to take you to the town of Southampton. Future guides will explore East Hampton, Montauk and a complete Hamptons brunch guide – but first, without further ado, our first stop:
What to Do in Southampton
- Beach, obviously – There isn’t a beach in the Hamptons that will leave you disappointed, but head to one of my two favorites for the most quintessential experience: Cooper’s Beach and Flying Point Beach. Picnic, swim, play, read, re-balance.
- Rent a yacht – I believe in playing hard. While this spring day was a bit to gusty for the boat experience, I talked to a few locals and plan on contacting True East Charters for future summer adventures.
- Go horseback riding – For those who love connecting with horses and this prime East Coast pastime, Gray Horse Farms is probably one of the few places in the world where animals are treated like royalty.
- Go on a wine tour – This unexpected part of the trip sent my Italian-countryside-loving heart into a swoon fest. The Hamptons is brimming with dreamy wineries and I’ll personally be doing the bike tour of wine country in late summer through Duck Walk Vineyards.
- Detox and focus on health – I love to use vacations as an excuse to eat extra healthy and take care of my body (and as a frequent traveler, this mindset is the only way to stay in shape and avoid overindulgence). The Hamptons are the perfect place to master that. Check out Hamptons Hot Yoga for a mind-body session or the LA-friendly-fitness-craze Tracy Anderson studio for the extra challenge; it’s in East Hampton, but this sweat is worth the extra 15-minute commute.
Where to Eat in Southampton
Breakfast: La Hacienda – Two words: breakfast burrito. A seaside must.
Lunch: Sean’s Place – Hearty-yet-modern quintessential American summer food.
Dinner: Tutto il Giorno – Wow worthy Italian food. If New Yorkers get addicted, there is also a Tribeca location.
Best Coffee in Southampton
While Starbucks are plentiful in the Hamptons, the only place you should even consider caffeinating is the Hampton Coffee Company. Not only are you supporting a local business cherished by locals, but also deepening this espresso haven’s rich history on the East Coast. Providing coffee to tourists, locals and stars since the 1940s, the Hampton Coffee Company has gone from one tiny windmill location to several locations and Long Island’s most influential and celebrated micro-roastery.
P.S. If the business owner reads this guide, kindly open up a Manhattan location. Just one. Or heck, even Brooklyn (it’s way cooler than Manhattan, anyway). OK? Thanks.
For those passing through Southampton – this will be your coffee stop address: 749 County Road
Where to Shop in Southampton
For all shopping desires, head to Main street! From Club Monaco, J. Crew and Ralph Lauren (my first pitstops on any shopping trip) to more locally owned boutiques brimming with New York’s finest runway resort wear, the villages prime shopping street is the go-to spot for locals and tourists alike for good reason.
I have to also mention how hopelessly charming these streets are…from a superfluous amount of patriotism-inducing American flags to small town heart the village exudes effortlessly, Southampton is easily the Stars Hollow of the Hamptons and forever deepened my growing obsession for the wholesome American lifestyle.
Where to Stay in Southampton
If you are looking for a cozy short-term stay (perfect weekend getaways), I highly recommend exploring one of these dreamy Southampton Inns:
For the longer holiday and summer vacation, these Airbnbs will deliver the prime Hamptons experience:
- The classic Hamptons villa (tennis courts and all)
- The historic Hamptons abode (all those photo opps…)
- The cozy and quaint cottage (but still undeniably luxurious)
How to get to The Hamptons
- Car is the route I always prefer in life – and this road trip is romantic in adventure and heart. Skip the main highway and take the 27A/Montauk Highway all the way to get the full experience of Long Island (seriously, such an inspiring American – albeit, elite – gem of tourism).
- From NYC without car, no worries: Hamptons-goers without cars (talking to you, 99% of Manhattanites) can take the Long Island Railroad or the famous Hamptons Jitney bus – easy, quick, affordable.