Best winter sailing destinations

a woman in winter gear stands on deck with sails in the background

Wondering where to head next this winter? With low sunshine levels and chilly temperatures in the UK, the beginning of the year can be the ideal time to seek warmer climes. And there’s no better place to do it on than a boat! From January to March, there are key parts of the world where you can rely on more pleasant conditions. But that’s not the top criteria for some sailing enthusiasts! We look at a range of winter sailing destinations, from the visually stunning to the technically challenging, the local to the tropical. There’s something for everyone in our winter destination top picks!

Winter Sun

If you need more than sea air to fully regenerate during the winter, a warm holiday sailing destination is for you. Team your passion for sailing with a holiday in the most traditional sense of the word. These destinations have longer days and the welcome relief that comes with calmer weather systems and reliable sunshine.


This French outpost in the Caribbean is a balmy and luxurious destination for sailing and relaxing alike. It’s a classic tropical paradise, with plenty of coves and hidden inlets to explore by boat. Stick to the west of the island, into the Caribbean sea, for the least challenging conditions. Daytime temperatures over the winter tend to be between 26 – 29°C with just over 11 average daylight hours. Plenty of time to explore and bask in the sun! 


This collection of islands off the east coast of Africa are a renowned holiday destination, whether you sail or not! With around 12 hours of sunshine and temperatures between 25 and 28°C over the winter, it’s easy to see why. For sailors especially, there’s plenty of opportunity to island hop, and marinas here are incredibly well equipped. There’s plenty of culture shoreside for those who seek it, but also more remote spots if you prefer peace and quiet.

Cape Verde

To the west of Africa, Cape Verde is a horseshoe shaped collection of islands. They offer some stunning and interesting geological sights as well as cultural hotspots when you step ashore, full of vibrant music and dance. You can expect on average 11 hour of daylight and temperatures between 21 and 26°C. Consistent breeze conditions and barely any rainfall make sailing a pleasant experience here. And there are plenty of spots beyond the tourist trail for those who like to explore.

Local Gems

Winter sailing in the UK is likely to be a more challenging option, with considerably less sunshine! There are more erratic weather systems, unreliable temperatures, and shorter days. However that doesn’t mean that you should discount the UK for winter sailing. British waters have a great deal to offer both in terms of scenic views and technical sailing. Plus, there’s the added advantage that our waterways are markedly quieter during winter months. All the better to really enjoy those stretches which can get congested during summertime. 

Plymouth Sound

The Devon and Cornwall coastline can be regarded as rather treacherous come winter. However, Plymouth Sound and its river offshoots are protected from unpredictable winter sailing conditions. Here, you can explore some stunning surroundings with plenty of interesting stop off points. There are four good quality sheltered marinas at Sutton Harbour, Queen Anne’s Battery, Mountbatten Yacht Haven and Mayflower Marina.

Orwell and Stour

Towards the east of the UK, head to the Suffolk and Essex coastlines for the Orwell and Stour rivers. These are leafy and well sheltered, with plenty of quiet anchorages along their shores. Not to mention a great choice of modern marinas. This is a great spot for a weekend of sailing that is quintessentially English.

Isle of Arran

The Firth of Clyde runs between Arran and Ayr on the mainland and is a relatively sheltered spot to sail in the Winter. Even so, the weather is considered to be of the “charm or challenge” variety. Though cold, days of crisp and fresh sunshine are a joy and give opportunity to spot the extensive wildlife. From dolphins and seals to sea otters and even eagles up ahead. Confident sailors may navigate calm nights by starlight and experience the Northern Lights. Or simply enjoy it all from the marina!

Other Ideas

Over winter, you may prefer to refine your sailing experiences to a different scope. Perhaps you could learn a new skill ready for the spring to roll round, refurbish your vessel, or network with like minded individuals. 

Training Courses

If you want to keep your experience up, or refine your skills winter is an ideal time to have a go. Course fees are often reduced over the winter, with less demand. So it’s an ideal time to get a qualification under your belt. In fact, the shorter days are ideal here as night sailing courses are more accessible. This means that when next winter comes around, you’ll be more equipped to explore domestic waters by night. Let’s not forget that quieter waters and marinas can mean less stressful exam conditions, making it an altogether more accessible time for learning. 

Boat Upgrading

It’s hard to find time to make all those aesthetic tweaks that you have in mind over the summer. Any downtime is often spent on the water, and by the time your boat is closed up for the winter soft furnishings are worn but you may not notice. It’s not until you get back on board that you realise quite how tired and unkempt your boat cushions have become! So the winter is an ideal time to reupholster your boat interiors and deck. From boat seats to cockpit cushions and even curtains, winter gives you the time to refit you vessel with quality bespoke products. 

Water Sports Show

The end of February sees the Royal Yachting Association dinghy and watersports show. This two day event is an opportunity to immerse yourself in like minded conversation and explore new products and designs. There are also numerous conferences over the winter months for members to stay connected. 

However you spend the season, winter shouldn’t be an activity desert for sailing enthusiasts. You can plan to get away, stick to your own shoreline, or take the opportunity to indulge in some off-water boating activities. Or perhaps you’ll give your boat the long awaited makeover you’ve been meaning to get to. To find out more about our bespoke upholstery services, just get in touch

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