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Top Holidays
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Winter Your Way: The best destinations for snow and sun

Inspiration | 09 December 2025

Winter holidays mean different things to different people.

For some, the season conjures images of spruce forests powdered in snow, ski lifts creaking skyward, and steaming mugs of glühwein by the fire. For others, the only white stuff they want to see is sand between their toes, paired with a chilled glass of something crisp and sun-dappled sea views. Whether you’re team snowflake or team sunbeam, the colder months deliver the best of both worlds – provided you know where to look.

We’re unpicking winter’s two distinct personalities. First, destinations where winter sun reigns supreme, offering balm for frost-bitten spirits. Then, the classics that remind us why snowy peaks and glowing chalets continue to draw travellers year after year. Whichever way you lean, these winter holiday destinations are designed to feel exceptional, effortless and truly memorable.

It’s time to winter your way with Winged Boots.

Flying south for the winter: our pick of luxury winter sun breaks 

Not everyone is built for thermals. A quick change of latitude or a hop across the equator is enough to trade icy pavements and winter coats for shimmering horizons and sunscreen. These winter sun holiday destinations shine brightest when the mercury dips elsewhere.

Winter holidays in the Maldives
View from One&Only Reethi Rah

Winter holidays in the Maldives

If anywhere was built for winter escapism, it is this scattering of atolls in the Indian Ocean. For balmy weather and postcard-worthy beaches, the Maldives meets the criteria as the best place to holiday in November. At this time of year, the skies stay clear, the seas calm, and visibility so good that snorkelling feels like slipping into a living aquarium. Villas hover above turquoise lagoons, chefs conjure dinners beneath the stars, and the sheer sense of space makes a welcome contrast to crowded pre-Christmas shopping centres. Turn your back on winter blues in favour of, well, a million other blues, courtesy of diving, sailing and island-hopping excursions.

As for accommodation? One&Only Reethi Rah is where private villas come with sweeping ocean views, discreet butler service and a choice of experiences that make the everyday feel extraordinary. If the idea of landing by seaplane and stepping straight onto sun-warmed sand doesn’t make you smile, we have questions.

Winter holidays Dubai
Sky Pool Villa at Atlantis the Royal

Winter holidays in Dubai

Searching for the best winter city breaks? Our winter is when Dubai really comes into its own. The city finds a comfortable rhythm, where beach days roll easily into evenings on rooftop terraces and desert adventures are best followed by late-night dining under the stars. Souks brim with colour, contemporary galleries add a cultural edge, and the sheer contrast of experiences keeps every day feeling fresh.

For a stay that captures it all, check in to Atlantis the Royal, where a two-kilometre stretch of private shoreline meets flawless service and restaurants that turn dinner into an event. Swap icy windscreens for warm sea breezes and let Dubai show you how winter can sparkle.

Best places to stay in Cape Town
View of the Mount Nelson, A Belmond Hotel, with Table Mountain in the background

Winter holidays in Cape Town

When Britain is bundled in coats, Cape Town is all sunshine and honey-paced evenings. Summer runs from December to March, with bright skies, warm days and that famous sea breeze keeping things comfortable; it is prime time for ocean drives, Winelands lunches and an unhurried cable-car glide up Table Mountain. Swap crowded high streets for vineyard picnics and waterfront sundowners, then sleep it off to the sound of the Atlantic.

After a city base with real personality? Try Mount Nelson, A Belmond Hotel: a candy-coloured Cape Town icon with manicured gardens, storied charm, and sunset views over Table Mountain that are well worth lingering over. To extend the journey with a safari, pair it with Eagles Crag Lodge, Shamwari Private Game Reserve in the Eastern Cape, where elegant lodges, expert guiding and abundant wildlife make the transition from city to wilderness completely seamless.

Wintry wonderlands: the best luxury winter holiday destinations for skiing and more

For some travellers, winter is not something to escape but something to savour. The hush after snowfall, the glow in alpine windows at dusk, the first glide on a freshly groomed piste; these are the quiet luxuries that make a cold-weather trip feel special. These December holiday destinations encourage you not only to embrace the elements, but celebrate them in all their glistening glory. 

Where to stay in St. Moritz Switzerland
Exterior view of Badrutt's Palace Hotel St. Mortiz

Luxury winter holidays in St. Moritz, Switzerland

St. Moritz may be known as one of the most exclusive resorts in the Alps, but it’s surprisingly down-to-earth once you’re there. The air has a clarity that makes colours pop, the pistes encourage confident, sweeping turns, and even a simple walk around the frozen lake feels special. Life off the slopes is just as rewarding: afternoons can melt into spa rituals, or into lunches that somehow stretch until sunset.

A stay at Badrutt’s Palace is like stepping into an Alpine fairytale with a glamorous twist. With over a century of history woven through its turreted silhouette and a legacy of impeccable service, this St. Moritz grande dame pairs old-world elegance with just the right amount of playful indulgence.

Best five star ski lodges in Courchevel
Living room in Chalet Alpensia, Courchevel

Luxury winter holidays in Courchevel 1850, France

This prestigious corner of Les 3 Vallées has been setting the gold standard in Alpine style for decades. The skiing is vast, with miles of groomed pistes that feel made for long arcs in the morning sun and winding forest runs that lead you gently home in the afternoon. There’s a festive rhythm to village life too: shop windows twinkle, fires roar in slope-side restaurants, and lunch has a way of becoming an all-afternoon affair.

Stay at L’Apogée Courchevel, where ski-in, ski-out ease is matched with chic interiors and a team who know exactly how to turn a snowy day into a celebration. Melding classic Alpine styling with the kind of cool that Courchevel does so well, it’s the kind of place where boots are kicked off and glasses are raised.

Best luxury hotels in Finland Lapland
Aerial view of accommodation at Arctic Treehouse Finland

Luxury winter holidays in Finnish Lapland

Lapland is winter at its most magical. Snow-laden forests stretch as far as the eye can see, the air crisp and bright, and when night falls the sky often dances with ripples of green and violet. Days here blend adventure with atmosphere – one moment you might be gliding behind huskies, the next wandering quiet forest paths lit by lanterns.

As darkness deepens, evenings settle into fireside suppers before bed at Arctic TreeHouse Hotel, where wide glass windows turn stargazing, and perhaps an aurora sighting, into a nightly ritual. Paired with extraordinary outdoor adventures and dining rooted in local flavours, it’s an unforgettable winter escape.

If you enjoyed this read but need more inspiration for your next winter break, take a look at our top five winter breaks to suit everyone.

Best places to go in winter
Skiing experience

The Winged Boots touch

How Winged Boots can shape your winter

A great holiday is more than its destination. It’s the way each piece fits together, from the flight that works with your schedule to the hotel room that feels made for you. In the sun, that could mean a villa perfectly positioned for sunset, snorkelling excursions timed for the calmest seas, or a private dinner set up on the sand just for your party. In the snow, it might be a suite with ski-in, ski-out access to your favourite run, a guide who balances adventure with leisure, or restaurant reservations that transform lunch into an occasion.

Winged Boots ensures your winter break, whether it’s basking in the tropics or carving fresh tracks in the Alps, is not just about being there, but about feeling completely at ease once you are.

Speak to one of our expert personal travel managers on 0203 318 6077 or enquire online now

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