9 Amazing Island Vacations to Book This Winter
If you lived through a winter polar vortex, you know that one needs an arsenal of coping mechanisms. On the plus side, the freezing weather is a great excuse to binge-watch your favorite TV series, splurge on a cozy parka, and indulge in hearty meals. But when temperatures drop well below zero and snow storms are seemingly an everyday occurrence, more extreme measures are called for. It’s time to consider an island vacation, where leafy palms, crystal-clear water, and endless sunshine await. Whether you’re looking for a quiet Caribbean hideaway or an exciting set-jetting hotspot, we’ve got you covered.
Vogue’s Guide to the Best Island Vacations:
- For Wellness: Sensei Lanai, a Four Seasons Resort, Lanai
- For Fishing: Salterra, a Luxury Collection Resort Spa, South Caicos
- For Privacy: Mandarin Oriental, Canouan
- For a Little Bit of Everything: Four Seasons Resort Koh Samui
- For a Private Island Feel: Soho Beach House
From snorkeling with sea turtles to day trip excursions on boats and bikes to lazy, laid-back hours spent lounging on some of the world’s most beautiful beaches, our favorite places offer a lot for every kind of traveler. Keep reading for our travel guide for the best places to visit this winter—each more bucket list-worthy than the last.
Lanai
Unlike other Hawaiian islands, Lanai’s arid climate creates a much drier landscape compared to lush Maui and verdant Kauai. That’s not to say it’s not green. While you’ll find swaying palms, there are actually more Cook pines here, which were strategically planted to capture fog drip. This is in stark contrast to Keahiakawelo’s Mars-like landscape of red dirt and towering boulders: The historic site and its nearby beaches are only accessible via a 4x4 or mountain bike, but it’s well worth braving the rugged terrain to visit and set your eyes on Molokai and Oahu on a clear day. And if you want to learn more about the island’s history and traditions, head into town to the Lanai Culture Heritage Center for educational programs, volunteer opportunities, and the annual Kupulau Festival.
You might not have beach access, but Sensei Lanai, a Four Seasons Resort, is a magical garden paradise sprawled across 24 acres with nearly a thousand species of plants. In lieu of sun and sand, the name of the game here is wellness. Four Seasons has teamed up with wellness company Sensei that results in a beautiful marriage of the former’s aptitude for hospitality with the latter’s results-driven programming (hello, thermal body mapping). The remarkable spa suites are kitted out with their own steam shower, infrared sauna, soaking tubs with UV light, and a pair of wading pools, one of which can be used for watsu. Aside from relaxation, there are also several fitness and mindfulness classes along with a nutritionist to answer all of your burning questions. Tailor your visit to suit your needs and filter in some leisure activities, like Jeep tours and sunset cruises. (And if you want a more traditional beach resort, Four Seasons Resort Lanai is a year-round hot spot just down the road.)


