sailing destinations

5 Top Sailing Destinations For Fall And Winter

There is nothing as exciting as a sailing vacation. With exotic locations, sandy white beaches, idyllic landscapes, and, not to forget, mesmerising sunsets, relaxation is no doubt the order of the day. If you adore boating, you can undoubtedly connect to the ecstasy and relaxation that come with sailing, even if all you do is sit back and take in the landscape while holding your favourite beverage.

Do you enjoy travelling and discovering new places? If so, you’re in luck, as there are lots of places to go sailing throughout the winter and fall. However, you must first address the question of choosing a boat. Booking a boat in the middle of fall and winter is almost impossible, so it is advisable to book a boat well in advance rather than at the last minute.

Additionally, checking out boats for sale is another option worth considering. Getting your own boat or yacht guarantees you a peaceful and more personalised experience as a solo traveller or with a group. Once the boat selection process has been taken care of, you can go ahead and pick from the popular fall and winter sailing destinations below.

The British Virgin Islands

In addition to the peaceful sound of the sea and beautiful beaches, the British Virgin Islands (BVI) also boast year-round warmth. This location is considered a perfect paradise and one of the best destinations for fall and winter. You can either explore the secluded beaches and caves or the busier towns. Whatever you choose, you should know one thing is for sure: you will enjoy every minute of your time on the islands.


Seychelles is known as one of the most colourful islands in the world, and it is surrounded by French culture. The country is calm and naturally stunning. Plus, when visiting in fall or winter, visitors get a taste of adventure and don’t forget an opportunity to sail among giant tortoises and seabirds.


Cuba is the largest Caribbean Island and a fantastic sailing destination. The crystal clear, bright blue waters of Havana never cease to amaze. Cuba is beautiful and full of bustling city life and colour, which makes it a perfect sailing location for a winter getaway. 


Another winter sailing destination worth visiting is the Grenadines. There are currently 32 islands worth exploring in the Grenadines. Located in the Caribbean, this relaxed and calm environment can do you a lot of good. In the Grenadines, you get an opportunity to explore scuba diving with turtles and other amazing features that make a boat ride to this destination worthwhile. 


Commonly called the “island of the winds”, visiting Mykonos in person is an experience that won’t be forgotten for a very long time. Mykonos is a peaceful and refreshing fall sailing destination. It’s no surprise this is one of the most exciting sailing locations as visitors get to explore the utopia of water sports, which is one of Mykonos’ sources of attraction. 


There are several appealing and pleasant sailing destinations for the fall and winter. Just a few of the many more are included in the list above. Plan a trip to these locations for a mind-blowing experience when you have the chance. All you need to do is make sure you’re willing to explore and have everything ready for a fantastic trip. Oh, and don’t forget your men’s sailing trousers!

Until next time.

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