There’s something special about having a trip in the diary. Grey January mornings feel a little different when you know you’ll be somewhere warm by February.
If you’re longing for winter sun in January 2027, or a little later in the season, this is my month-by-month edit: where I’d go, where I’d stay, and the small details that make all the difference.
Why plan your winter sun now
Planning early means you get first choice of everything: the hotels I’d most love to send you to, the suite with the sea view, the villa with the shaded pool. The rooms worth having are limited, and returning guests tend to book them well before Christmas, especially around February half term.
It also gives us time to get the little things right, the champagne waiting for you on arrival, the kids club sessions confirmed, the spa treatments booked. That’s the part my clients notice most when they arrive, it’s all in the detail.
January: Anguilla and the Maldives
Mid January onwards is one of my favourite months to travel. It’s tucked between the Christmas rush and February half term, so many of the best places are calmer, and rates are often kinder too.
Anguilla. For calm seas, dry days and very long lunches on Meads Bay. January brings around 28°C, and the island has 33 beaches, no cruise ships and a lovely, unhurried vibe. It’s the kind of Caribbean island people return to year after year and rather like to keep to themselves. Where I’d stay: Cap Juluca, whose white domed villas curve along the soft sand of Maundays Bay. You step from your terrace straight onto the beach, and the sunsets over St Martin are a lovely end to every day.
The Maldives. January is when the water is at its clearest, and the marine life really shows off: turtles gliding over the reef, rays and little reef sharks in the shallows, and shoals of brightly coloured fish just off your villa steps. With more than a thousand islands, choosing the right one is most of the work. Where I’d stay: that depends entirely on you, so I’ve written about my five favourite Maldives islands, by type of traveller.
February: Cape Town and St Lucia
February is when I get asked most about half term, and both of these work beautifully for couples and families alike.
Cape Town and the Winelands. Cape Town is right in the middle of its summer, but the busy festive weeks are behind it. Long sunny days, the sea at its warmest, the grape harvest beginning in Franschhoek, and a day driving the Peninsula. There’s no jet lag at all, as it’s only two hours ahead of us. Where I’d stay: Ellerman House in Bantry Bay, then three nights in the Winelands at Babylonstoren. It’s always the part my clients talk about most when they get home.
St Lucia. Classic Caribbean sunshine, with temperatures between 26°C and 30°C, and the Pitons rising straight out of the sea. Rainforest walks, the warm volcanic springs near Soufrière and long Creole lunches by the water. Where I’d stay: Sugar Beach, tucked into the bay right between the two Pitons, with its villas set among the trees above a soft white beach. It’s one of those places where you look up from your sunlounger and can hardly believe the view.
March: Tulum and Sri Lanka
By March the evenings at home are getting lighter, and both of these are at their sunniest.
Tulum, Mexico. Laid-back, boho beach style, warm Mayan culture and hot, dry weather. Mornings at the clifftop ruins above the Caribbean Sea, afternoon swims in the cool, clear cenotes, and dinners under the palms. It’s about an hour and a half’s drive south of Cancún, which has direct flights from London. Where I’d stay: Hotel Esencia, once the private estate of an Italian duchess, on a quiet stretch of beach at Xpu-Ha, a short drive north of Tulum. It feels like staying at a friend’s beautiful beach house.
Sri Lanka. Surf-chic beaches, a rich Buddhist heritage, and hot beach weather paired with misty tea hills. From December to March the south and west coasts are warm and dry. I love starting near Kandy, home to the Temple of the Sacred Tooth Relic, then a few cool days in the tea country, a couple of nights looking for leopards in Yala National Park, and finishing on the south coast, where Weligama’s gentle waves are lovely for a first surf lesson. Where I’d stay: Santani, a peaceful wellness retreat in the hills outside Kandy, then Ceylon Tea Trails in the tea country, Wild Coast Tented Lodge on the edge of Yala, where the jungle meets the beach, and Cape Weligama on the coast.
Something worth knowing: time difference matters more than distance
When I’m helping someone choose winter sun for a week or ten days, I look at the time difference before the flight time. Cape Town is a long overnight flight, but it’s only two hours ahead, so you land ready to enjoy it and come home without feeling it. Heading west to Anguilla, St Lucia or Tulum, you’re four or five hours behind home, which most people find easier than flying east: you wake early, just in time for the best of the morning. The Maldives and Sri Lanka are five hours or more ahead, which is lovely for a longer stay but worth planning around with young children.
Where will you be escaping to this winter?
Tell me how you’d like to feel at the end of your first week away, and I’ll tell you where to go. Leave the rest with me. Start planning your winter sun →