Holiday Destinations

The Best Winter Sailing Destinations

Do you live in a country where winter means cold piercing rain and snowstorms? But you dream about that relaxing summer sun all year round? We are aware that summer is just around the corner and you are already planning your sailing holiday for 2019. However, if you like planning ahead and you are already sure that this year you want to be having fun and be warm no matter the season, then we have something for you. In this blog, we present to you the best winter sailing destinations all over the world. We hope this list of the top winter sailing destinations will inspire you and by the end of it, you will know where to sail to when you want to replace the cold winter wind with warm exotic sunshine.

The British Virgin Islands

The amazing British Virgin Islands has lately been appearing in many dream destination related articles. From The Best Sailing Destinations for Beginners to The 10 Best Party Islands in the World. However, we are not surprised considering how beautiful, versatile, and rich these islands are. So here they are again, grand opening another list of top destinations, this time for winter sailing.

The perfect destination for your dream winter holiday is The British Virgin Islands. The excellent weather conditions for cruising and the crystal clear water of the Caribbean Sea can be enjoyed from January all the way through May. We advise you to start your island-hopping adventure in Tortola, which is the largest island in the Caribbean island chain. We also encourage you to venture further out! Explore the beauty of one of the Caribbean’s most celebrated countries in this winter season.

Social distancing is possible on the British Virgin Islands. It is recommended to travel there within the months of September and November, right before the crowded cruising holidays start.

The Grenadines

The Grenadines are the escape you need if you dislike the cold winter weather. If you prefer the warm Caribbean sun, we will not be surprised. The Caribbean Islands offer plenty of beautiful places you can explore, and it’s the perfect sailing destination. If some people you know are going skiing, you can swim and discover secret beaches there at the same moment. Out of 32 islands, only 9 are inhabited, but all of them are utterly stunning with lush nature and clear blue waters surrounding them.

Remember, Tubber is always here to help you find the perfect charter yacht in the Caribbean and in many other places. It’s easy, safe, at the best price and supported by experts, who are ready to answer all your questions 24/7.


Thailand is undoubtedly one of the most desired winter getaway destinations. Especially if you plan to explore it by boat. Since Thailand is such a popular winter destination, the beachside resorts can be very crowded. Going on a sailing holiday in Thailand offers the solution to this problem. Exploring the Andaman Sea is a more relaxing and authentic experience than just staying in a hotel. Furthermore, these turquoise waters offer smooth sailing, while the white beaches and the sun are guaranteed to cure the winter blues.

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Sailors can enjoy the fantastic conditions of Thailand’s beautiful coast from November to April. Here the famous island of Phuket adds to the whole dream holiday experience with its colorful nightlife and endless beach parties. Whether you are a party animal, a sailor, a beach lover, or a foodie, Thailand has something to offer for everyone.

Bearing in mind Thailand attracts the largest groups of visitors, it is not suitable for social distancing. However, it is the perfect place for those seeking a lively destination.

The Canary Islands

The Canary Islands is also one of our top picks for the dream winter sailing holiday. This Spanish archipelago, situated off the coast of Morocco is the home of tropical rainforests, black sand beaches, and alluring natural swimming pools. If you decide to sail there you will be gazing the stars from your own private yacht. If you re an experienced sailor, the waters of the Atlantic Ocean will be suitable for you. They can offer you excellent conditions and trade winds even mid-winter. However, no worries if you’re not. You can always enjoy a boating holiday in the Canary Islands if you hire a skipper with your yacht charter.

We advise you to visit Tenerife, which is one of our favorite Canary Island. It even made it in our list of The Top 3 Canary Islands for Sailing Holidays.

Between March and May, and September to November, are the best periods for those who are seeking social distancing. Before and after these periods, the Canary Islands are very touristy and not suitable anymore for social distancing.


Last on our list with great winter sailing destinations are Seychelles. Breaking up the grey winter days with a vacation on a sunny island is always a good idea. Deciding where to go however can be pretty hard. Especially, since you have so many options. Well, maybe we will make things even harder, but we just have to offer you one more destination. The consistent summer climate all year round, the beautiful waters of the Indian Ocean, and the dream beaches make Seychelles a destination we just can’t miss to mention. This place is rightfully known as the dream honeymoon destination, but we think it can be much more especially if you charter a yacht and go on a sailing adventure. You still get the romance, but with a bit of spice and nights under the stars in the middle of the ocean.

It sounds like a dream, doesn’t it? Well, tell us what you think in the comments below or on our Facebook page. Remember, you don’t have to wait until summer to enjoy sailing. Now you can start planning your own dream winter or summer sailing holiday with Tubber.