Of course, there’s absolutely nothing wrong with a pool day, especially when home is dark by four and the weather has been miserable for weeks. But seven identical days of lounger, buffet and room can leave a holiday feeling strangely forgettable, and winter sun is so much better when the warmth makes getting out easier. The trick is choosing a place where sunshine is part of the trip instead of being the entire itinerary.

Make Spain more than a resort booking

Spain is the obvious place to start, but that doesn’t mean automatically disappearing into the nearest all-inclusive. The Canary Islands are particularly lovely in winter because the official tourism board says temperatures rarely drop below 20°C, while the islands offer volcanic walks, historic quarters and stunning landscapes as well as beaches. 

Tenerife can be split between the south coast and the greener north: spend one day around La Laguna and Anaga, another near Teide, then keep the beach for when you fancy it. Gran Canaria gives you Las Palmas, local food and the island’s mountainous interior within reach of the resorts. When comparing a cheap Spain holiday, look at the map before the hotel photos and choose a base with useful bus routes or straightforward car hire. If bright winter days matter more than guaranteed heat, Palma is also brilliant for culture, cocktails and harbour walks, although Mallorca will feel cooler than the Canaries.

Walk and eat your way around Portugal

Madeira is perfect if doing nothing for a week sounds more tiring than doing something, and Funchal makes an attractive base. Beyond the city, the levadas turn the island into a walking holiday without requiring every outing to be an epic summit attempt. Pick a route that suits your fitness, book a guide if heights or changeable weather make you nervous, and leave enough time for late lunches. The scenery shifts quickly between deep green forest, waterfalls, mountain cloud and huge Atlantic views, which is why staying beside one pool feels like such a waste here. 

Before setting off, check Madeira’s official live information for classified walking routes, as paths may be open, restricted or inaccessible. A day outside also makes poncha and espetada back in Funchal feel deserved, which is my preferred balance of activity and indulgence.

Treat Malta as a sunny city break

Malta works best in winter when you stop expecting beach weather and plan it as a compact city-and-coast break instead. Base yourself in Valletta for grand harbour views and beautiful limestone streets. Cross the water to the Three Cities, spend a day wandering Mdina and Rabat, then take the ferry to Gozo for coastal paths and village squares. The islands are small enough to keep journeys manageable, but varied enough that you can change the plan if wind or rain arrives. A loose itinerary earns its keep here, but there’s more practical planning in this guide to making the most of a Mediterranean holiday if you want it.

Swap the sunbed for Morocco’s streets and coast

For a bigger change of scene without a long-haul flight, Morocco gives winter warmth a completely different atmosphere. Marrakech is the obvious first-time choice, but the best days don’t need organised entertainment from morning to night.

If you have a full week, combine the city with Essaouira. Its ramparts, fishing port, galleries and Atlantic walks make a refreshing contrast to Marrakech, and the journey gives the holiday two distinct halves without creating a frantic itinerary. 

Winter evenings can be chilly, especially inland, so a sunny rooftop lunch and a riad with a cosy communal space are more useful than a swim-up room. Leave one afternoon unscheduled too; getting slightly lost, finding a courtyard café and watching the medina change towards evening is part of the point.

The best winter-sun trip is the one that still gives you a reason to get dressed in the morning. Choose a walkable base, plan one or two proper days out, leave space for food and spontaneous stops, and keep the pool as an option. You will still come home rested, just with better stories than which lounger you managed to claim.