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Find your perfect Labor Day weekend trip

Whether you’re traveling with your partner, family or besties, we’ve got your Labor Day weekend plans covered. | By Tanvi Chheda | July 15, 2022 (Updated August 28, 2024)

Tanvi Chheda

Formerly an assistant editor at Travel + Leisure, Los Angeles-based Tanvi Chheda has been freelancing for 15 years now. She writes mostly about lifestyle and travel, which often spills into arts & culture, food, design and more. With two young children, family travel is also a passion of hers. Given her South Asian heritage, she writes about India quite frequently as well (she was born in India and speaks three Indian languages). When not traveling or writing, she enjoys reading, cooking and spending time outdoors. Her work has appeared in the New York Times, the Wall Street Journal, AFAR, Virtuoso Life Four Seasons magazine, Qantas, Inspirato, Invited, Pasadena magazine, OLTRE and Ciao Bambino, among others.

Headshot of author Tanvi Chheda

There’s no doubt that travel is back as friends and family reunite, eager to share authentic experiences and make new memories together. This Labor Day weekend, you choose your companion(s) and we’ll point you to the right destination.

Two young women eating ice cream of Santa Monica pier and having fun
You'll find live performances, amusement park rides, delicious eats and more at the Santa Monica Pier.

Los Angeles: For the photo-friendly crowd

If #summerfun is your love language, then laid-back LA — with its sun, surf and Hollywood glam — is the perfect place to spend the long holiday weekend.

First things first, hit Santa Monica’s famed beach and pier, and get a bird’s-eye view of the California coastline while on the solar-powered Ferris wheel. Santa Monica is also home to some 130 street murals, including James Goldcrown’s colorful “Bleeding Hearts/ Lovewall,” along Montana Avenue, a favorite among shutterbugs. Snap some pics and drop into M&D at Margo’s Kitchen, an all-day eatery nearby. Or spend the day at the Getty Center, where works like Van Gogh’s “Irises” rival the architectural marvel they are set within.

If hiking is your thing, head up to the Griffith Observatory and take a few selfies with the city’s biggest name, the iconic Hollywood sign. For a night on the town, start at Piccalilli, a Southeast Asian-inspired restaurant in Culver City, and dig into creative dishes like Thai chicken katsu and miso pork jowl. Leave room for dessert, like scoops of honeycomb and Sicilian pistachio at Van Leeuwen’s, which has an outpost at the trendy Platform, an outdoor shopping complex with indie boutiques.

Two men and two women toasting with champagne while sitting on a boat.
A private yacht charter makes for ideal oceanside lounging in Miami.

Miami: For the luxury seeker

Summer lasts all year long in Miami, the land of sun, palm trees, swanky rooftops and a bona fide contemporary art scene. Start your getaway by snagging a table at the award-winning Uchi, where the 10-course omakase dinner boasts mouthwatering seafood delicacies. The city’s museums and galleries are a requisite stop. A favorite? The 200,000-square foot Perez Art Museum Miami, which boasts international art from the 20th and 21st centuries and a climate-responsive design by Herzog & de Meuron.

When you’re ready to take a break from the art immersion, consider chartering a yacht for the day or relaxing at one of the city’s many wellness facilities — all between hours spent lounging on Miami’s golden beaches, of course. If retail therapy is more your style, head straight for the Miami Design District to snag the latest fashions, innovative housewares, one-of-a-kind jewelry and more.

Teen girl is hugging her sister near pond in front of the Washington DC Capitol during the summer.
Including the Washington Monument, there are over 160 monuments and memorials to explore in Washington.

Washington: For the family traveler

With its monuments and museums, a history-themed trip to Washington is on every family’s bucket list. For a more engaging sightseeing excursion, consider a guided bike tour to cover must-see sights such as the Lincoln Memorial, Thomas Jefferson Memorial, Washington Monument, Martin Luther King, Jr. Memorial and more. Older kids may prefer to take in Washington’s landmarks from the water on a kayaking adventure with Potomac Paddlesports.

With some 70 museums in the District, you and your brood will likely only scratch the surface. A few not-to-miss spots, though, include the National Air and Space Museum, Smithsonian Institution, International Spy Museum and United States Mint. After long days exploring, you can kick back with some pool time or a movie in bed. Embassy Suites by Hilton Washington DC Georgetown offers both, as well as complimentary evening snacks, ample amenities and a prime location (cult-favorite Georgetown Cupcakes is a quick 20-minute walk away) in the heart of Washington.

One must-stop for Labor Day weekend? DC JazzFest, a two-day, family-friendly celebration of jazz music at the Wharf. This year marks the festival’s 20thanniversary so it’s sure to be an even bigger party than usual in 2024.

Friends drinking beer at brewery pub.
An Austin getaway promises feasting and fun for all.

Austin, Texas: For the group getaway

With its relaxed, chilled-out vibe, Austin is an easy destination to get the gang together for a long weekend of indie music, craft breweries, inventive eats and lake life. Fuel up at Veracruz All Natural, a local chain known for its breakfast tacos, before embarking on a beer crawl to hit some of Austin’s top craft breweries such as Hold Out Brewing and Jester King brewery. Get a flight of IPAs, porters and ciders (Austin and its outskirts boast some 58 craft breweries).

Austin’s food truck scene is the stuff of legends. No really, the city has literal food truck parks — Arbor Food Park or Thicket South Austin Food Park are two faves — where dozens of eateries will gather so locals can feast all in one place. But for a sit-down meal consider Grizzeldas, which matches a pretty interior with modern Mexican dishes, or Uchiko, sister to sushi restaurant Uchi, which got its start in Austin. End each night with live music at Mohawk. Prefer to swap city life for days on the lake? You and your friends can rent a boat with Float On boat rentals and enjoy a chilled-out weekend on Lake Travis.

Japanese Maple in Fall
Fall in love with your surroundings (and each other) at the Portland Japanese Garden.

Portland, Oregon: For the romantic couples' trip

For the couple looking to get away from it all, Portland checks all your boxes. Featuring bike trails, fine dining and wine country to explore, this West Coast city is the perfect choice for a romantic getaway. Stroll hand-in-hand through the serene 12-acre Portland Japanese Garden, which features dense evergreens, moss-covered rocks, intimate wooden bridges and meandering streams. This time of year, the Japanese maples will also be putting on a show, turning fiery red and golden yellow, as they get ready to shed their leaves.

If you and your love want an active vacation, consider hopping on a bike (Canopy by Hilton Portland Pearl District offers complimentary bike rentals to its guests) and cycling through downtown’s Waterfront Walking and Biking Connection. The Pearl District is also the site of the annual and free Art in the Pearl Fine Arts and Craft Festival, which runs over Labor Day weekend and brings more than 100 local artists together to exhibit and sell everything from paintings and ceramics to photography and jewelry.

Come evening, lovebirds can choose from one of several tasting menus at French-inspired Le Pigeon, helmed by James Beard Award-winning chef Gabriel Rucker, or Coquine, which serves dishes such as spring lamb ragu with Swiss chard and ricotta dumplings. Follow with cocktails and highballs at the Multnomah Whisk{e}y Library, a moody lounge with leather chairs and antique chandeliers, not to mention a 1,500-whiskey bottle wall.

Your Summer Stay

From beachside resorts and all-inclusive luxury to serene spas, we are ready and waiting to be the home base for your summer adventures.