Six Stellar Staycation Ideas for Labor Day Weekend

While Labor Day is often thought of as the last opportunity to escape the city before summer ends, it’s also an ideal time to indulge in a staycation. Cities are emptier, it’s easier to get a coveted restaurant reservation, and there’s no shortage of activities to occupy you (plus the beach will still be nice – and less crowded – the following weekend). If you’re not sure of your Labor Day plans, we’ve rounded up some ideas for how to play tourist in your hometown this upcoming holiday weekend.

New York

Stay: Equinox Hotel

There’s no better place to forget you’re in the city than this wellness-focused hotel. Indulge in a spa treatment, lounge at the pool, take in a workout and find a much-needed moment of zen before heading back to face the world on Tuesday. Learn more >

Eat: Greywind

For fresh dishes featuring local ingredients, head to Greywind in Hudson Yards, the newest restaurant from chef Dan Kluger. He recommends the sugar snap pea salad or focaccia with housemade ricotta and rhubarb. And of course, don’t leave without trying the house made "cheese-its.” Learn more >

Do: The US Open

There are matches happening all weekend long, including the round of 16 starting Sunday. Plus the Equinox Hotel has partnered with BLADE to offer guests the chance to fly on a helicopter straight to the player’s entrance of the tournament, with a direct trip back. Learn more >


Stay: Chicago Athletic Association Hotel

It’s easy to overlook the classics in the city where you live, but that’s why a staycation is the perfect opportunity to rediscover what made you fall in love with your city to begin with. Enter: The Chicago Athletic Association Hotel, the 130-year-old building with sweeping views of Millenium Park and Lake Michigan beyond. Head to the rooftop bar, Cindy’s, for a late night cocktail on the breezy terrace. Learn more >

Eat: Asador Bastian

If you think you know what a steakhouse is, think again: this newly opened chophouse serves up beef with a Spanish flair, in particular one special cut the Txuleton. A staycation calls for indulging, so also be sure to check out their excellent dessert menu from renowned pastry chef Hsing Chen. Learn more >

Do: Watch a movie (in a park)

The Chicago Onscreen festival runs from August 28-September 2 and features 9 outdoor screening events of local films. The screenings take place in parks throughout town and are a wonderful way to celebrate the city on a warm summer evening. Learn more >


Stay: The Langham Boston

Named one of the best hotel transformations of 2022 by Condé Nast Traveler, this historic hotel reopened in 2021 after a massive face lift. Now, it offers stately and luxurious guest rooms where you’ll delight in retreating to after a long day sightseeing. Learn more >

Eat: Giulia Restaurant

Not much beats Italian food done well and that’s exactly what you’ll get at this hot spot. All the pasta is incredible, in particular their pappardelle with wild boar. Just make sure you make a reservation now; they can be notoriously difficult to snag at this hot spot. Learn more >

Do: Fireworks and Museums

Not many cities host a fireworks show for Labor Day. Enjoy this only-in-Boston experience by booking a boat tour to take you right in the middle of the action. During the day, we recommend heading to ICA Boston, which will be offering free admission all day Monday if you’d like to take in some art as well as the soon-to-close ICA Watershed.

San Francisco

Stay:  The Fairmont San Francisco

Perched in aristocratic Nob Hill, this classic hotel is the perfect place to rediscover your city for a long weekend. At the very least, the incredible views and ample spaces for high end dining and drinking will make you feel like you’re living in Hitchcock’s  “Vertigo” (in a good way). And if you really want to feel like a tourist, the famous views at Top of the Mark hotel bar are right next door. Learn more >

Eat: Dalida

One way to experience San Francisco in a new way is to allow yourself to be awed by spaces and places you thought you knew. Enter Dalida, a new Mediterranean restaurant that is located directly in the Presidio park. And the location is not the only special thing about it; come for the classic Middle Eastern food like fattoush salad and kibbe and stay for the more fabulous and less familiar dishes like Turkish dumplings (manti). Learn more >

Do: Catch a baseball game

In our minds, there’s no greater summer activity than watching a baseball game while enjoying  a cold beer and a hotdog. And Labor Day weekend is a great time to take one in as the Oakland A’s will face the Los Angeles Angels in a thrilling series happening all weekend long. Learn more >

Los Angeles

Stay: Conrad Los Angeles

Travel + Leisure’s 2023 World’s Best Awards rank Conrad Los Angeles as #6 in the Top 15 Favorite City Hotels in Greater Los Angeles category. Heralded by the vision of legendary architect Frank Gehry, the hotel is an elegant oasis with 305 modern rooms, a rooftop terrace with private pool deck, full-service spa and locally inspired dining. Discover energizing experiences that will ignite your inspiration. Learn more >

Eat: Agua Viva

If there’s anyone who could combine Latin and Asian flavors successfully, it’s José Andrés who knocks it out of the park at this trendy spot. Featuring beautiful views of downtown and delicious beachy dishes like “build your own handrolls” and grilled skewers, the restaurant is the perfect spot to bring a group of friends for a very fun night out. Learn more >

Do: Jean-Michel Basquiat Exhibition at The Grand

This blockbuster exhibit from New York is now open for a limited time at The Grand. Featuring 200 previously unseen works, the exhibit provides a special view into the work of the legendary artist. Make sure to buy your tickets in advance to snag a good time slot. Learn more >


Stay: Riggs Washington DC

This beautiful hotel is located in the former Riggs National Bank and that theme shows up in playful touches around the hotel; each room is inspired by a private safety deposit box while the lower level bar is housed in a private bank vault. Don’t miss the Café Riggs, their European-inspired brasserie featuring a refined all-day menu. Learn more >

Eat: Chang Chang

While the takeout from this modern Chinese restaurant is excellent, we highly recommend sitting down for a meal to get the full experience. Ideally for the crispy Peking Duck, the Sichuan Lazi Chicken and the pan fried crispy noodles. Order a ton and take leftovers home with you – trust us, they’ll get eaten. Learn more >

Do: Go to the Museum

DC has no shortage of free and fun attractions to do, but when you’re a resident it’s sometimes easy to forget that. So why not use this weekend to take full advantage of the incredible range of museums and sites? From the National Museum of African American History and Culture to the Hirshhorn, there is a museum to fulfill literally any interest.

The Related Life is written and produced by the Related Life Editorial Team. Be sure to follow us on Facebook and Instagram for the latest events, news, and announcements in your area, and tag us for a chance to be featured @therelatedlife and #therelatedlife.