That is the big question we're raising this week.
First things first ... you're not going to be able to travel with carry-on only. Then again, when you crack the daily double - a destination where you can enjoy a winter wonderland and summer spoils in less than 24 hours - checking your gear is a secondary concern.
Some destinations are famous for having snow and sand options just hours from one another. Surf Taylors Mistake near Christchurch in the morning then drive two hours to Mt Hutt, one of New Zealand's best resorts, for a powdery afternoon. Heck, you don't even need a passport, with Perisher less than three hours' drive from surf breaks on the NSW South Coast.
In southern California, it's only 160 kilometres from LA - where you can surf, swim or swagger at Malibu or Huntington - to Big Bear ski resort. Less well-known are Morocco (surf at Taghazout, ski at Oukameden) and Chile (Pichilemu and Valle Nevado).
Just 1.5 hours from the ski resort, you can plunge your jelly legs into the Mediterranean.
Founder and CEO of adventure travel website We Are Explorers, Henry Brydon, recommends southern Spain. "The Sierra Nevada is a beautiful mountain range near Granada with an impressive range of ski options," he says. "What makes it special, though, is that just 1.5 hours from the ski resort, you can plunge your jelly legs into the Mediterranean. My pick is Carabeo Beach, hidden away near Nerja."
She's been all over the world, but World Expeditions CEO Sue Badyari can't go past Borneo for its wide-ranging wilderness. "You can be on top of Mount Kinabalu at 4095 metres, where the temperatures can be at freezing, and be back in the tropical jungle or balmy coastal areas around Kota Kinabalu in the late afternoon." Badyari recommends sunrise at the summit and retaining some energy for the latter stages of the day.
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"The Kinabalu National Park at the base of Mount Kinabalu is home to orangutans, sun bears, a variety of colourful kingfishers, trogons, pittas and many more," she says.
There are some more surprising places, too. On Hawaii's Big Island, Mauna Kea, the highest peak in the Hawaiian state, and Mauna Loa, located in Hawaii Volcanoes National Park, are often covered in snow. You can't ski or snowboard thanks to hidden lava rock, but there are hikes to Mauna Loa's white peaks and a stargazing tour on Mauna Kea. Otherwise get set for a night snorkel with manta rays in Keauhou Bay. Water temperature in winter? About 22 degrees.
Not sold on the sea? Utah's Park City is surrounded by world-famous ski resorts like Deer Valley, plus is only a half-hour drive from Homestead Crater, a geothermal spring hidden in beehive-shaped limestone rock. Once inside, sink into water that's a toasty 32 to 36 degrees, and swim, snorkel, scuba dive or even take a paddle board yoga class.