Travel, Deeply Considered

Where to Go on Holiday in Winter 2026 — Our Picks

Every year, the same question arrives with the September rain: where should I go this winter? The answer changes year to year — new properties open, flight routes shift, and some destinations become genuinely better or worse depending on what has happened in the world. These are our specialists’ picks for winter 2026 — the destinations they are actively recommending to clients right now, and why. The Maldives — Still the Benchmark The Maldives remains the single most requested winter sun destination among our clients, and for good reason. December to March is peak dry season, the water is at its clearest, and the resorts are at their most polished. Soneva Fushi in the Baa Atoll, One&Only Reethi Rah, and the new Patina Maldives are all exceptional choices. The caveat: Christmas and New Year in the Maldives is the most expensive two weeks in luxury travel. If your dates are flexible, early January or February offer identical weather at significantly lower prices. Barbados — The Caribbean at Its Most Refined The west coast of Barbados in winter is perfection. Calm turquoise water, golden sand, and a culinary scene that has quietly become one of the best in the Caribbean. Sandy Lane remains the benchmark, but Cobblers Cove and The Sandpiper offer a more intimate scale. The flight from London is direct (approximately 8.5 hours), which makes Barbados one of the most accessible Caribbean islands. Kenya — Green Season Safari January and February in Kenya is green season — the landscape is lush, the light is extraordinary, and the camps are quiet. This is not Migration season (that is July to October), but the resident wildlife in the Masai Mara is excellent year-round. Amboseli is at its absolute best in January, with clear views of Kilimanjaro against blue skies. Prices are 20–30% lower than peak. Thailand — The East at Its Most Welcoming November to February is Thailand’s dry season — warm, sunny, and the humidity drops to manageable levels. Koh Samui, Phuket and Krabi are all excellent. For something more distinctive, consider Chiang Mai in the north — cooler temperatures, temple culture, and the night markets at their vibrant best. Oman — The Desert at Its Most Comfortable Oman in winter is one of the Middle East’s best-kept secrets. Temperatures hover around 25°C, the air is dry and clear, and the landscape — dramatic wadis, ancient forts, empty coastline — is at its most inviting. Alila Jabal Akhdar, perched on the rim of a canyon in the Al Hajar mountains, is one of the most striking hotel locations in the world. Sri Lanka — Two Coasts, Two Seasons Sri Lanka’s weather splits by coast: the south and west coasts are dry from November to March, making this the ideal winter window. The tea trails of the hill country are at their greenest. Combine south-coast beaches (Tangalle, Weligama) with cultural triangle temples (Sigiriya, Dambulla) and a few days in the highlands for one of the most varied short-haul winter trips available from the UK. Dubai — The Obvious Done Well Dubai in winter is not subtle and does not pretend to be. But at its best — a desert camp at sunset, a table at Nobu on Palm Jumeirah, a morning at the souks before the crowds — it delivers a particular kind of luxury that no other destination replicates. December to February temperatures are perfect (22–28°C). The flight is short (7 hours). The family infrastructure is world-class. South Africa — Safari Meets Coast December to February is summer in South Africa. The Cape Winelands are at their most beautiful, Cape Town’s beaches are warm, and the Eastern Cape safari reserves (Shamwari, Kwandwe) are in excellent game-viewing condition. Combine Cape Town, the Garden Route and a Big Five safari for a winter trip that covers everything. Mauritius — The Quiet Indian Ocean Mauritius is warmer and slightly wetter than the Maldives in winter, but the west coast (where the best resorts sit) remains reliably sunny. One&Only Le Saint Géran, LUX* Le Morne and The Oberoi are all excellent. Mauritius offers more to do beyond the beach than the Maldives — markets, rum distilleries, nature reserves, a genuine local culture — which makes it a strong choice for travellers who get restless after three days of doing nothing. Antarctica — The Ultimate Winter Escape December to February is the Antarctic summer — 20 hours of daylight, temperatures around 0°C, and the ice retreats enough for expedition vessels to navigate the channels and peninsulas. This is the most extraordinary trip we arrange. Scenic Eclipse II offers the most luxurious expedition cruise experience currently operating. Book 12–18 months ahead — the best cabins sell fast. Every destination in this list, from the Maldives to Antarctica, is ATOL protected when booked through HighStreet Holidays (No. 12118). Your money is secure, your flights are included, and your specialist handles every detail.