Aspen
If you’ve never tried Aspen in the summer, you’ve been missing out. Underneath the snow lies stunning nature to hike, bike and paraglide through. Trickling rivers provide perfect conditions for fly fishing, and long golden hours at sunset bathe the mountains in picture-perfect orange glow. Foodies rejoice in some of the best, freshest food there is. And the elite local community draws some of the world’s best chefs. If you haven’t tried Sushi Nakazawa, we think you should. And there’s no dearth of dinner options, from prime rib at Steakhouse No. 316 to branzino at Duemani.
Where to stay
As if we haven’t harped on Little Nell enough, we’re going to do it some more. The only five-star diamond ski-in/ski-out experience caters to the top of the food chain. Which means that every nook and cranny, from the lobby to residence balconies, is designed as a backdrop for a celebrity photoshoot. The Kardashian-Jenner clan is known to spend winters here.
Chicago
We might be biased, but we are pretty darn sure that Chicago is one of the best cities in world. You have shopping, food, beautiful art and culture, and of course, the laid-back Midwestern way of living. On Labor Day weekend, book a cabana at the Shore Club Chicago. Yes, there is a legitimate sandy beachfront that you had no idea was so beautiful. Also for this weekend, outdoor festivals are back, so there will be no shortage of outdoor music from some of the best musicians in the world. Rooftop bars and restaurants are prime for the gorgeous city view. And we recommend hitting up Nobu.
Where to stay
If you haven’t decided to eat and also stay at Nobu (which we highly recommend), then consider our hands-down longtime favorite in the city: the Peninsula. From A+ service and seamless Covid protocols to the most sparkling clean rooms even pre-Covid, the hotel will make you feel confident in your safety and well-being. Rooms have spacious interiors with five-star amenities like Nespresso machines and luxury linens. The hotel itself features a large pool and lush spa with breathtaking views.
Istanbul
For a Labor Day weekend, this may just be the best idea you’ve had in a long time. Before buckling down into another fiscal year, spend some time immersing yourself in this historic, geographically exquisite city. Nothing changes your perspective quite like the Hagia Sophia, a museum dating back to AD 325. From the Topkapi Palace to the Basilica Cistern, there’s no shortage of Ottoman era architecture and relics to explore. At night, Taksim and Tunel feature lively nightlife for tourists and locals alike. In the summer months, we recommend getting a taste of the culture in the outdoor markets and festivals. Every corner has an ancient building or hole-in-the-wall restaurant worth discovering. Start a new season off right by seeing the world through the lens of another culture.
Where to stay
It’s surprisingly hard to choose where to stay in Istanbul because even the four-star hotels are stunning. But we have to recommend Six Senses Kocatas Mansions. The newly renovated resort is the perfect place to stay in the city. You get beautiful views of the Bosporus Strait and the ultimate experience. Add in the luxury status of Six Senses, and it’s a recipe for success. Though you’re stepping into a historic Byzantine palace, modern sustainability is at the forefront of the portfolio’s efforts.
Tuscany
In case this summer was not relaxing enough for you, we think you should head to Tuscany. There’s no better place to chill out. You can spend your days cafe hopping through the hillsides on a Vespa. There is no shortage of day trips, but your itinerary doesn’t need to be booked to the hour to make the most of this trip. The Tyrrhenian Sea features crystal clear waters and rocky coastlines to explore. We recommend sailing to the island of Elba to hit up a beach club and go scuba diving. For those who prefer staying on land, small towns are perfect to cruise through in a rented Ferrari. Of course, you’re in Italy, so eat all the pasta and gelato you can.
Where to stay
It’s a self-care weekend, so you’re staying at Fonteverde Tuscany. The remote resort might be more spa than anything else, but we’re not complaining. With seven pools, a wellness and fitness center, and endless treatment options, you could spend the whole weekend going from one rejuvenating experience to the next. And to top it off, exquisite, healthy food and picture-perfect views make the resort unbeatable.
Douro Valley
For those whose vacation is not complete without good wine, we have you covered. Welcome to the oldest demarcated wine region in the world: Douro Valley, Portugal. And Labor Day is a great time to visit, not only because of the gorgeous sunsets but also because it’s peak production time. As you probably know all too well, port wine is sweet and dreamy, and fortified to retain the extra bit of flavor and alcohol. When you stroll through the vineyards from quinta to quinta (those adorable wine-producing estates), you’ll understand why the wine is so good. It’s made with love in the best environment. When you’ve had enough to drink, you can take a boat cruise along the Douro River, deemed one of Portugal’s “crown jewels.” Oh, and you physically can’t go hungry. Charcuterie boards here are unlike anything you’ve ever tasted, and the salted cod, octopus salad and meat stews are hearty and well worth the calories.
Where to stay
Six Senses Douro Valley. We’re realizing that this article is turning into a Six Senses feature, but we promise there’s just nowhere better to go. For wellness lovers, Six Senses is the ultimate destination for relaxation. Not only are there serious spa treatments and seductive pools, but the grounds are so stunning that you can’t possibly be stressed when walking through them. If you have a remote job, you may even consider never returning home. Connecting with the surrounding forest and river brings the kind of calm you can only dream of. And enormous windows in the contemporary rooms keep you feeling perpetually connected to the land.
