8 Last-Minute Labor Day Weekend Getaways You Can Still Squeeze In
If you’re shocked at how fast summer has flown by, chances are you’re in good company. But don’t worry—there’s still the lovely, long Labor Day Weekend ahead to enjoy the last legs of the season. Even though it’s only a few short weeks away, there’s still plenty of time to book a getaway, and we’re here to inspire your last-minute trip with top Labor Day destinations across the country.
Stefanie is a New York–based writer and editor covering travel, architecture and design, art, science, history, and more. She's worked on staff at Architectural Digest, ARTnews, and Oyster.com, and has contributed to Condé Nast Traveler, Popular Science, History.com, and Mental Floss, among others.
Palm Springs, CA
For decades, Palm Springs has called away Los Angelenos and other West Coasters to its beautiful golf courses, relaxing spas, historic mid-century modern architecture, and stunning desert setting: in essence, it’s the perfect getaway for the last weekend of summer. There are dozens of iconic hotels to stay at, from the young and sceney Ace Hotel & Swim Club with its lively pool scene to the serene L’Horizon Resort & Spa, a luxurious hot spot that's hosted Hollywood legends and a number of U.S. presidents. For Labor Day weekend, our pick is the Saguaro Palm Springs, a colorful resort that blends relaxation and fun. When you've had enough of the pool, borrow a desert cruiser bike to explore town.
Asbury Park, NJ
The Jersey Shore has a bit of a reputation, but in recent years, the beach town of Asbury Park has established itself as a hip retreat far away from those fist-pumpers you might have seen on TV. The picturesque boardwalk makes for a quintessential East Coast seaside setting, lined with beachy boutiques, fantastic food stalls, and spots to sip cocktails. There’s also the legendary Stone Pony, a concert venue that’s hosted the likes of Jersey legends Bruce Springsteen and Jon Bon Jovi. The place to stay this season is The Asbury, a hip boutique hotel with two rooftop bars, a pool, and lots of throwbacks to the area's music days.
Chicago might not be the first place you think of when picturing a Labor Day Weekend retreat, but hear us out: it’s got beaches along Lake Michigan, plenty of rooftop bars and pools for lazing the day away, and a clutch of super hot hotels packed with excellent dining options. Plus, you can’t beat the city's arts and design scene, from the legendary Art Institute of Chicago to a slew of Frank Lloyd Wright–designed houses and the ever-popular Chicago Architecture Foundation river cruise. While there’s no shortage of cute boutique hotels to choose from, we recommend booking a stay at The Robey in Wicker Park, which has an incredibly fun rooftop Cabana Club with bites, booze, and a pool.
Key West, FL
What do you get when you combine history, beaches, and vibrant nightlife? Key West, the southernmost island in the Florida Keys where conch fritters, locally distilled rum, and all-day happy hours reign supreme. Ernest Hemingway was one of Key West’s most famous residents; today you can visit his home on the island, which is now a museum. There’s also Harry Truman’s “Little White House,” which he visited 11 times over the course of his presidency. For a relaxing stay that’s still within walking distance of all the action, check in to The Marker, a boutique spot with three pools (one is adults-only), a poolside bar that hosts tequila tastings, and beach-chic guest rooms decked out in soothing blues and whites.
The desert oasis of Scottsdale, Arizona, might be best known for its spas and golf courses (which are absolutely worth the trip,), but it’s also a great dining and cultural destination, too. Fuel up at chef Charleen Badman’s FnB for veggie-forward dishes paired with delicious vintages before tours of Taliesin West (Frank Lloyd Wright’s winter home and studio) and the fantastic James Turrell Skyspace at the Scottsdale Museum of Contemporary Art. Somewhat surprisingly, Arizona also has a burgeoning wine industry; in downtown Scottsdale, you'll find no less than six tasting rooms by different wineries. After a tasting or two, rest your head at the recently renovated The Scott, a hotel designed by AvroKO to channel Havana in the Southwest, where you can sip on Caribbean-inspired cocktails by the pool.
New York City
Labor Day is a perfect time to visit the City That Never Sleeps, since a good portion of the local population heads out of town for the weekend. (That also makes it a great staycation spot!) From Broadway shows to museum visits, there are limitless activities across the city to fill your time, but for some classic holiday weekend action, head out to the Rockaways for a day at the beach or one of the city’s beautiful parks for a picnic. Alternatively, you can book a stay at The William Vale in Williamsburg, Brooklyn, whose rooftop pool has become one of the biggest and most sought-after swimming spots in the city. You can’t go wrong with drinks and a bite at the hotel’s equally popular Westlight restaurant, which features superb views of the Manhattan skyline.
Unlike the central and southern reaches of the East Coast, Portland, Maine, enjoys relatively temperate summers—though it’s still warm enough to head to to the beautiful, pine-lined beaches of the region. The small coastal city is a delightfully calm spot to escape for a few days, with plenty of seafood restaurants, fantastic shopping in the Old Port, and fun boating tours on the water. Housed in the landmark Portland Press Herald building, The Press Hotel, Autograph Collection—with its whimsical riffs on the newspaper theme (headlines scrawled on hallways; typewriter-themed installations) and a destination restaurant in Union—is a great home base for exploring the best the city has to offer.
Isle of Palms, South Carolina
There's no denying the charm of Charleston, what with its dreamy plantation homes, incredible restaurants (we recommend Husk, but you’ll have to make reservations in advance), and historic Fort Sumter. For a breezy escape still within striking distance of the city’s attractions, however, consider booking a stay on the Isle of Palms. This low-key spot just north of the city is mostly about the beach, but, thanks to the island's clutch of quaint restaurants and bars, we wouldn't blame you for staying stay put all weekend long. At the Wild Dunes Resort, you'll find everything you could want in a perfect Labor Day weekend escape, from golf courses to pools, beachside restaurants, water sports, activities like basket-weaving and fishing, and even a spa.
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