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Winter travel often looks like one of two things: Battling against the cold weather or surrendering to the sun. Here at Condé Nast Traveler, it’s a mix of surf and ski, from the crystal clear waters of Costa Rica’s Peninsula Papagayo to the snow-capped mountains of Park City, Utah. For such outdoor adventures, we’re cataloging the very best in rash guards, waterproof shoes, goggles, and ski suits that will carry us from wave to slope. It’s not all winter games, though. Some of us plan to do little else besides spend time at home with our loved ones, keeping in mind the cashmere sweaters and sweatpants we intend to live in for days on end. Here’s where we’re going and what we’re packing this winter to stay comfortable and cozy from takeoff to touchdown.
Hitting the slopes in Park City, Utah
This winter, I’m headed on a ski trip to check out the brand new expansion of Deer Valley Ski Resort—which will make the space one of the largest ski resorts in North America. (In fact, it’s one of our best places to go in the US for 2026 for that very reason). I’m still on the hunt for the perfect accommodation for me, but some top contenders are the Grand Hyatt Deer Valley and Sundance Mountain Resort, either one a good home base for mornings on the slopes and long, bright days exploring (or heading to the spa). Aside from my checked luggage (to which I’ll probably share with my partner), I’ll be packing light in one of my favorites duffels, the chic Carra Portobello, with pieces I reach for without thinking—say, my soft Madeline Swan Crew for warming up. For the slopes: my Smith Squad goggles and the Halfdays merino base layers that disappear under my fun and red one-piece suit. And once I’ve hit enough runs—when all else winds down and everyone drifts toward town—I’ll pull on my Edelweiss Henley, slip into my Vallon Glacier shades, and settle easily into some après-ski fun. —Jessica Chapel, commerce writer
Hiking and eating our way through Lima and Mancora, Peru
Every December or January, I decamp to Peru for a couple of weeks—to see family and friends, but also to take advantage of those Southern Hemisphere summers. This year, in addition to surfing and eating my way through Lima, I’ll be heading north to the Mancora area for, well, more of the same, at a much slower pace. I always bring my Melissa rubber fisherman sandals, which pull double duty as swimming shoes at rocky beaches and cute sandals for when it’s time to throw on a cover-up and head to lunch.
For less waterlogged days—and for the journey down to Peru—my instant-classic leather M. Gemi flats are a shoe-in. Clothing-wise, I’m packing a capsule wardrobe so I can save room for things I want to buy (in Lima, I like to pay a visit to Mozdeh Matin’s showroom and Angela Kusen’s KA Concept Store, plus the Mercado Surquillo for food goods). On this trip, that’ll look like my Gil Rodriguez cotton button down tank (I have it in Black and Tomate), and a pair of perfectly worn-in Stan Ray shorts that I scored at Goodwill. I still need to firm up where we’re staying, but a friend just sent me a link to this beach house, which looks totally perfect. —Megan Spurrell, associate articles director
Returning home, Hallmark-movie-style, to Toronto
While I don’t have any exciting winter plans this year, I do have a trip booked: home for the holidays. I grew up outside of Toronto, and I’ll be heading back to Ontario mid-December for some family time, home-cooked meals, and hopefully a white Christmas. I’ll be dressed in my comfies the majority of the time I’m there, and right now I’m loving Mersea’s cashmere collection, specifically the Parma travel pants and Lugano sweater, for travel days and nights at home. My Roots sweatpants are also a classic every time I’m in the Great White North, because I’m never not going to support a Canadian-born brand! Of course, I’ll likely also go out for a few dinner-and-drinks dates with hometown friends while I’m back, so I’ll also be packing some more upscale outfits that are still warm and cozy. I have Rachel Antonoff’s espresso martini mockneck sweater in my Rent the Runway cart for an on-the-nose holiday ‘fit, and my brown Magnanni Audrey boots will surely complete the look (I’ve been getting so many compliments on them!). —Hannah Chubb, senior commerce editor
Surfing along Costa Rica’s Peninsula Papagayo
As the weather begins to turn, I’ve already reached denial over the arrival of winter—so much so, I’ve decided to fly down to Costa Rica for a final burst of sunshine before the holiday period sets in. I’ve visited the Central American country multiple times, and trips there always act as a salve and a reset for me, where days are largely structured around trying to learn how to surf, baking myself like an iguana under a palm tree, and trying to consume as much fresh papaya as I possibly can. This time, I’ll be staying at the Four Seasons Resort Costa Rica at Peninsula Papagayo on the North Pacific coastline, meaning my wardrobe for the week will largely be items for the beach (the property is bookended by two), including my trusty Hunza G one piece, a playful pair of tortoiseshell sunglasses from Swedish brand Sun Buddies, and a classic L.L.Bean canvas tote bag to hold all the key necessities like books and sunscreen (I’m a big fan of this SPF by Lesse). For surfing, I’m making sure to bring a lightweight rash guard and the Ceremonia Guava Protect and Repair kit to take care of my hair in the aftermath. —Lale Arikoglu, articles director
Experiencing the sublime at Banff National Park
This season I’m headed on a bucket-list trip to Banff National Park in Alberta, Canada. Even better, I’m staying at the dreamiest hotel I’ve ever seen: The Fairmont Chateau Lake Louise. The hotel’s backdrop is practically a winter wonderland with its turquoise-blue lake and snow-covered mountains. I’ll be spending most of my time checking out the hotel’s brand-new Basin spa, but I’m also eager to explore its hiking trails. Packing for cold-weather destinations can be tricky, but I’ll definitely need some reliable gear to keep me warm in Alberta’s below-freezing temperatures. With this in mind, I’m packing plenty of warm layers that are lightweight and breathable enough for an active day outdoors. Alo’s Gold Rush puffer is pretty warm when it’s worn on top of a fleece pullover or a cashmere sweater, but It’s not too heavy or bulky to pack in a suitcase. I’ll be wearing these buttery-soft Luxform leggings from Set Active and my go-to sneakers from Hoka. The Clifton 10s are so comfortable and offer pretty decent traction for walking on icy and slippery sidewalks. And because there’s nothing I hate more than my ears being cold, I’m also planning to slip this thick headband in my carry-on. —Meaghan Kenny, commerce editor
Visiting friends and family in the sunshine state
Over the holidays, I’ll be heading down to Florida to visit friends and family on the west coast and in the panhandle. Coming from New York, I’m very much looking forward to the warmer weather in Venice, so I’ll be packing my flip-flops, SPF, and accessories for lots of outdoor walks. Over the summer I purchased my first pair of Havaianas in more than a decade—they were a staple in middle and high school, but I didn’t have much use for them in NYC and forgot what a great vacation shoe they are to wear to the beach or pool (and so affordable!). In other shoe news, I recently purchased another pair of Hoka Clifton 10s to use as a walking-around shoe that doubles as a workout class or running sneaker while on vacation. I’ll probably wear those on the plane, along with these cozy wide-leg Athleta pants (with a zipper pocket!). —Madison Flager, associate commerce director
A momentous occasion in Bentonville, Arkansas
I am going to Bentonville, Arkansas in early December for a few days for something very special: my step-cousin’s husband’s Bar Mitzvah. Having missed their small, pre-Obergefell wedding, I wasn’t missing this! I don’t go on any longer trips without my Tumi Madeline cosmetic bag (my maroon one is still going strong after four years!) and its jewelry case. For walking around town, I will definitely be bringing my knit wool Uniqlo midi skirt (from a handful of seasons back; the brand has these now), which packs like a dream and is great for the day-to-night transition. I’m very proud to be nursing after 14 months, so this will be my second season with my Solly Baby Stormy Houndstooth nursing cover. I’ll have my maroon MZ Wallace Crosby Traveler for easy access to my stuff as my personal item, and my magenta waxed canvas Kanken bag (bought for a soul-filling solo trip to Ireland in 2017) as a diaper bag. For shoes, I’m definitely packing my patent ruby red Tieks. —Emily Newhouse, contributor, research
