AVENUE’s Last-Minute Labor Day Getaways

Wednesday, August 15, 2018

Say it ain’t so! Summer is almost over, which means that the amount of time you have to lock in your Labor Day plans is dwindling. Because we want you to be able to skip off to somewhere fabulous without getting bogged down by all the details, we’ve put together some dazzling itineraries for a few of our favorite weekend travel destinations. And if you’re not up for leaving Manhattan or you can’t get any further than the Hamptons, fear not. We’ve got some fantastic ideas to make your Labor Day weekend unforgettable, too.

Martha’s Vineyard

Pretend you’re a Kennedy for the weekend at Winnetu Oceanside Resort in Martha’s Vineyard. Located on South Beach at the southern tip of the island, the resort offers a tennis club, two heated pools, yoga classes and daily shuttle service to picturesque Edgartown. And if you can’t decide between Martha’s Vineyard and nearby Nantucket, enjoy what the folks at Winnetu call their “Two Island Adventure” by taking the ferry to its sister property, The Nantucket Hotel and Resort, for an overnight stay. Just make sure to sample Michelin-Star Chef Joseph Keller’s french cuisine at his Nantucket bistro, Company of the Cauldron, before you take the ferry back to Hyannis.


There’s a reason why New Yorkers are constantly flocking to this southern getaway for the weekend. Only a two-hour plane ride from JFK, the charming city of Charleston is both steeped in history and stacked with some of the best bars and restaurants you’ll find south of the Mason-Dixon. After you’ve dined on some chilled crab ramen and knocked back a couple craft cocktails at 5Church Charleston, which, as the name suggests, is set in a former church, crash for the night at the award-winning French Quarter Inn just around the corner. Just don’t forget to make time for the Ghosts of Charleston Tour, which includes an after-dark walk through the nearly 250-year-old Unitarian Church Graveyard. Now that we mention it, you might want to enjoy the creepy ghost tour before you’ve imbibed.


You bore the miserable heat in the city all summer and you work really hard, so needless to say, you’ve earned a Labor Day weekend of luxury at Rosewood Bermuda. Occupying 200 acres along the largest private beach on the island, the British-seaside-style resort is the idyllic travel destination for the New Yorker who’s in dire need of some R&R. There are a million and one things to do in Bermuda, like kayaking along the reefs, enjoying live music in Hamilton and taking in the majestic sunset at Fort Scaur in Somerset, but nobody will judge you if you stay in your oceanfront cabana all weekend.


Year round, Miami is a go-to destination for a weekend of revelry, so why not say so long to summer in the seaside city where you’re always guaranteed to have a good time? Starting September 1, Scarpetta’s Chef Scott Conant is hosting a daily specialty pop-up every day in Scarpetta’s lounge, where you can order a cold-brew infusion or even create your own bespoke cocktail from house-infused spirits and syrups. Later, score a Window Table reservation at Bleau Bar, which is where you want to be if what you want to be is seen. After you’ve recouped with a late morning/early afternoon nap on South Beach, give yourself a boost by munching on some fresh ceviche and guacamole at the Farmers Market on Lincoln Road. And for a late dinner before an even later night at Delano, enjoy Chef Makoto Okuwa’s famous Edomae-style sushi at his eponymous restaurant, Makoto, located in Bal Harbour Shops.

Stowe, Vermont

If you felt like your tennis game was lacking this summer, here’s your chance to improve your serve while staying at one of the best resorts in all of New England. Topnotch Resort offers what they call the Tennis Game Changer package, which includes luxury accommodations and either a one-hour private lesson or a two-hour tennis academy. Tucked away along Vermont’s Mount Mansfield, the resort also features an Equestrian Center and a 35,000-square-foot spa with every amenity you can imagine. If you happen to venture off the resort, grab a kayak and enjoy an afternoon paddle along the Winooski River before heading into town for some live music and cocktails at The Matterhorn. At Topnotch, you’ll find the breath of New England fresh air you’ve been craving after a long summer of smog in the city. Lastly, if you can’t wait for Labor Day for your fix of top-notch tennis, check out the Stowe Mountain Lodge Classic, which brings pro tennis to the town in anticipation of the U.S. Open.

New York

Believe it or not, there’s a lot happening north of the GW Bridge. Weather permitting (fingers crossed!), spoil yourself with a stroll through Fort Tryon Park at the northernmost tip of Manhattan. Hidden among the park’s lush gardens is the Met Cloisters, where the couture fashion of the groundbreaking Heavenly Bodies will be on display until October. A few blocks south of Fort Tryon is Chef Nicole O’Brien’s famous chicken sipping broth and lamb shank at the The Pandering Pig. And if you’re not craving French-inspired California cuisine, a fabulous second option is Saggio’s on 181st Street, the coziest Italian restaurant you’ll ever come across with some of the most delicious homemade pasta in Manhattan.

For those unwilling to make the trek uptown, peruse the work of up-and-coming artists at the Washington Square Outdoor Art Exhibit, which has its own venue on East 13th Street, then grab an egg, pancetta, and avocado sandwich at Estela on East Houston. After sunset, it’s Chelsea’s Gallow Green, the rooftop bar that everyone talks about. Located atop the McKittrick Hotel (yes, the same one that hosts Sleep No More, the interactive theatrical experience your friends have raved about), the flower-woven trellises, strung lights, and craft cocktails are what New York City nights are all about. Also at the McKittrick is the limited-run dining experience, The Lost Supper, which includes a tantalizing performance, three-course supper, half bottle of champagne her guest, and beer, wine and prosecco. 

The Hamptons

If you can make it to East Hampton by Friday night, enjoy a signature cocktail and artisanal plate at Nick & Toni’s (owned by restaurateur Toni Ross), which is hosting its last Social Hour of the summer on the 31st. In Bridgehampton, reopening Labor Day weekend is Salt Drift Farm, the rustic farmhouse eatery that serves the perfect meal over which to bid adieu to summer, like Baja Fish Tacos and their Hot Buttered Lobster Roll. Work it off during a Saturday night dance session at Jue Lan Southampton, and if that hasn’t done it, squeeze in a workout at TruFusion, the one-stop fitness shop for which New York Yankee Alex Rodriguez is an ambassador. And when all you need is a relaxed vibe where live music plays and the palm trees sway, Lynn’s Hula Hut in Montauk has an ice cold margarita with your name written all over it.


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