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When the holidays are over and winter really kicks in, planning a sunny escape can do wonders for your mood. Even if it’s hard to imagine yourself in a swimsuit in the middle of January, there are plenty of places where the sun is shining, the water is warm and the wind is just right for a sailing holiday.
Here are our favourite destinations for a January 2026 getaway – whether you want full-on tropical vibes, gentle winter sun in Europe, or a yacht charter with or without skipper on Click&Boat.
Saint Martin & St Barts
Half French, half Dutch and fully Caribbean, Saint Martin is a great base if you want a mix of relaxed island life and a bit of buzz. In January, you can expect around 26 °C, trade winds blowing steadily and warm, clear water.
From Marigot or Oyster Pond, you can charter a catamaran with skipper and hop between Anguilla, Tintamarre and glamorous St Barts. Days are spent snorkelling with turtles, swimming in turquoise bays and enjoying beach bars at sunset.
❤️ Our highlight: sailing to St Barts for the day, dropping anchor in Colombier Bay and hiking up for the view over the anchorage before heading back on board for a sundowner.
Guadeloupe & Martinique
If you’d like to stay in a French-speaking environment but still escape winter, Guadeloupe and Martinique are hard to beat. January is the start of the dry season here: sunshine, low humidity and ideal sailing conditions, with the trade winds well established. It’s also considered high season because the weather is so good.
Fly into Pointe-à-Pitre or Fort-de-France, step aboard your sailboat or catamaran and set off between Les Saintes, Marie-Galante, the bays of Le Marin or Les Anses d’Arlet. Anchorages are often well protected, and sailing distances are short. It’s perfect if you’re travelling with family. If you don’t know how to choose between Martinique and Guadeloupe, we recommend you check out our guide!
❤️ Our highlight: a day at anchor in Les Saintes, combining a morning hike to the viewpoint with an afternoon swim in crystal-clear water.
Canary Islands
Want to escape the cold without flying too far? The Canary Islands offer a softer kind of winter sun, ideal if you prefer 20 °C to 30 °C. In January, air temperatures usually sit between 16 °C and 20 °C, with cooler evenings – bring a light jumper for nights on deck.
From bases in Tenerife, Gran Canaria or Lanzarote, you can charter a monohull or catamaran and explore a mix of lively marinas and wild anchorages. Think black-sand beaches, volcanic landscapes, dolphins riding the bow wave and long downwind legs under the trade winds.
💡 Tip: winter can bring swells on the Atlantic side, so check local forecasts carefully and lean on your skipper’s advice if you’re new to the area.
Thailand
If you’re dreaming of dramatic cliffs, emerald water and long-tail boats, Thailand is a fantastic choice for January. Around Phuket and the Andaman coast, this month falls right in the dry season with temperatures close to 28 °C and generally calm seas : perfect for island-hopping by boat.
From marinas around Phuket, you can charter a boat on Click&Boat and sail through Phang Nga Bay, Krabi and the Phi Phi Islands. Expect sheltered anchorages, good snorkelling and spectacular sunsets behind jagged limestone silhouettes.
❤️ Our highlight: spending the night at anchor near Railay, going ashore for dinner on the beach and watching the cliffs glow orange as the sun sets.
Mexico
For those based in North America, Mexico’s Caribbean coastline is a classic January escape. Around Cancún and the Riviera Maya, days hover near 28 °C, the sea is warm and conditions are great for relaxed cruising.
From Puerto Cancún or Puerto Aventuras, you can sail to Isla Mujeres or Holbox, stopping in shallow turquoise lagoons along the way. Combine time at sea with visits to Mayan sites like Tulum or Chichén Itzá for a winter break that’s not just about beaches.
💡 Tip: plan your sailing outings in the morning when winds are usually lighter and the light is at its best for photos.
Enjoying January on the water with Click&Boat
Whether you choose the French Antilles, the Canary Islands, Thailand or Mexico, January is a brilliant month to recharge before spring. With Click&Boat, you can:
- Rent a boat with or without skipper, depending on your experience
- Choose from catamarans, sailboats, motorboats and more
- Talk directly to boat owners to fine-tune your route and on-board experience
Step aboard, leave the grey skies behind and start the year with a horizon of blue.
FAQ – Sailing holidays in January
Where is the best place to sail in January?
If you want guaranteed warmth and clear water, head to the Caribbean (Saint Martin, Guadeloupe, Martinique, Mexico). For milder sun closer to Europe, choose the Canary Islands; for tropical scenery and great value, Thailand is a top pick.
Can you actually swim in the sea in January?
Yes. In the Caribbean and Thailand, sea temperatures are usually around 26–28 °C, perfect for swimming and snorkelling. In the Canary Islands, the water is cooler but still swimmable for most people with around 19–21 °C.
Is January a good month for a sailing charter?
Absolutely. Many tropical regions are in their dry season, with steady trade winds and calm seas. You’ll also avoid the crowds of July–August in places like the Caribbean and Thailand, while still enjoying great weather.
Do I need a licence to rent a boat in these destinations?
It depends on the country and the type of boat. In most places, you’ll need a recognised licence for bareboat charters, but you can always book a skippered charter on Click&Boat if you don’t have one or simply want to relax.
Which destination is best for a relaxing, low-effort trip?
If you want an easy winter break with short sailing legs and plenty of beach time, opt for Guadeloupe & Martinique, Saint Martin & St Barts, or a skippered charter in Thailand where your captain handles navigation while you enjoy the ride.
