Yes, We’re Already Booking Winter Getaways

We know—it feels early. You're just pulling out your linen pants and dreaming of rosé by the sea, and here we are talking about winter travel. But if you've ever tried to snag a beachfront suite for New Year's or a ski-in chalet in Aspen, you’ll understand why we’re already deep into planning mode for winter getaways.

Whether you're dreaming of sun-drenched beaches or powder-covered slopes, now is the time to start planning. Mexico’s Riviera Maya, Los Cabos, and the Caribbean islands are perennial favorites for travelers seeking warmth and turquoise waters when the weather turns chilly. Think boutique beachfront resorts and fresh ceviche under a palapa.

For others, winter means mountains—and we love that too. From the iconic slopes of Aspen and Jackson Hole to the snow-dusted villages of the French and Swiss Alps, ski season brings its own kind of luxury: crackling fires, fondue feasts, and fresh powder runs. Destinations like Courchevel, St. Moritz, and Zermatt book out months in advance—especially during festive weeks—so planning now means you’ll actually get the lodge or chalet you’ve been eyeing.

And let’s not forget the ultimate year-round escape: Hawaii. Winter is one of the best times to visit, with mild temperatures, whale watching, and dramatic sunsets on islands like Maui, Kauai, and the Big Island. Top resorts fill fast, but booking early gives you access to prime room categories, upgraded views, and exclusive perks.

The truth is, booking early isn't just practical—it’s stress-relieving. It means you’ll have the best selection of rooms, flights, and experiences, and can look forward to your trip without the last-minute scramble. Plus, with our insider access, we can often secure preferred rates, room upgrades, resort credits, and more—but only while availability lasts.

So yes, we’re already booking winter getaways. And if you want that perfect beachfront villa, ski chalet, or ocean-view suite, it’s time to start the conversation.

Let’s make next winter the one you actually look forward to.