Dream Winter Sailing Holidays

Are you longing for a paradise of palm trees, warm waters, cool cocktails and exotic landscapes? If so, it’s time to start planning a winter getaway. 

Zizoo’s Favourite Destinations For Dream Winter Sailing Holidays

Tortola, British Virgin Islands

dream winter sailing holidays

Tortola. Image by Garrett / flickr.

The British Virgin Islands are the ideal destination for dream winter sailing holidays. Enjoy great conditions for cruising on the crystal clear Caribbean Sea January through May. We suggest you start your island hopping adventure in the British Virgin Islands in Tortola, the largest island in the Caribbean island chain. With its powdery white beaches, vibrant beach bars and luring parks, you may want to spend your entire sailing holiday in BVI discovering Tortola, but we encourage you to venture further out to explore the pure beauty of one of the Caribbean’s most celebrated countries. Check out our 7-day sailing route in the British Virgin Islands to inspire your itinerary and learn more about sailing conditions and things to do and see on your next winter boat holiday in our guide to sailing in Tortola.

Contact us to get the best deals on yacht charters in Tortola.


dream winter sailing holidays

Martinique is famous for its hybrid sport that combines scuba diving and snorkelling.

As an overseas territory of France, you can expect to spend your dream winter sailing holiday in Martinique relaxing in one of the Caribbean’s most charming and chic destinations. Known for its gorgeous beaches and tropical rainforests, Martinique is a true paradise on earth. When not relaxing on your yacht or snorkelling in the clear waters that surround Martinique, we suggest you spend time exploring the alluring tropical landscapes and the historic treasures found in Fort-de-France. From it’s active volcano to an enchanting botanic garden, the island of Martinique offers a wealth of activities for those looking for a romantic winter getaway or family holiday. Sailing in Martinique also allows you to explore the best of the island and the nearby Windward Islands of Grenada, Saint Lucia, Saint Vincent and the Grenadines, Dominica. You might also want to sail to Barbados to get a taste of the Caribbean party island lifestyle. Start planning your sailing holiday in Martinique with our guide.

Find both budget-friendly and luxury yacht charters in Martinique.


dream winter sailing holidays

Explore the alluring coasts of Thailand this winter.

Thailand remains one of the most desired winter getaway destinations. Its warm climate, lovely beaches, exotic treasures and relaxing atmosphere makes it a haven for those who may have caught the winter blues. But did you know that Thailand also an excellent winter sailing destination? Sailors can enjoy pleasant conditions for cruising along Thailand’s most beautiful coasts and islands from November until April. The popular island of Phuket is one of the most popular locations to charter a yacht in Thailand and gives you a chance to explore the beauty of Phang Nga Bay and the Phi Phi Islands. Choose to spend time around the popular beaches in Phuket where you’ll find endless beach parties or take your yacht to some of the more secluded spots like Yacht Haven.

Let us help you find the perfect chartered yacht in Thailand.


dream winter sailing holiday

Enjoy relaxed sailing in Cuba.

The buzzing, colourful country of Cuba should be on every sailor’s bucket list. From December through March, you can escape the dark, cold days of winter and discover the Caribbean’s largest island by boat. Some of the best cruising grounds in Cuba are found around its southern coast where you can begin your sailing holiday at the harbour of the UNESCO World Heritage centre of Cienfuegos and set sail towards the tranquil Canarreos Archipelago. This island cluster provides great opportunities for snorkelling, diving and other water sports whereas the warm hospitality of the locals, vibrant nightlife and history provide a unique Caribbean experience. 

Charter a yacht in Cuba this winter.

Canary Islands

dream winter sailing holiday

Discover the dreamlike coastal and volcanic landscapes that characterise the Canary Islands.

The Canary Islands recently made it on our list of the top 5 sailing destinations in 2017 and is also one of our picks for dream winter sailing holidays. The Spanish archipelago off the coast of Morocco is home to an intriguing mix of volcanic and tropical rainforests. Enjoy black sand beaches, impressive gardens, alluring natural swimming pools and nights spent gazing at the stars from your own private yacht. The Canary Islands are perfect for experienced sailors accustomed to sailing in the waters of the Atlantic Ocean where you can expect excellent conditions thanks to the Trades Wind even in the midst of winter. If you are not up to the challenge of the Atlantic, you can still enjoy a boat holiday in the Canary Islands if you hire a skipper with your yacht charter.

Discover Lanzarote, one of our favourite islands in the Canary Island chain.

Why wait till summer to enjoy a sailing? Start planning your own dream winter sailing holiday with Zizoo. Read more about some of the most popular sailing destinations here and find more sailing tips, routes and suggestions of things to do and see while on your sailing holiday in one of over 30 countries in our magazine