Where to Sail in Winter

May 09, 2025 4 min

When the cold sets in, why not trade icy mornings for sun-soaked decks and endless blue horizons? Winter sailing is the perfect way to escape the chill and explore warm, tropical waters.

This guide will transport you to some of the most breathtaking places to sail during the winter months, where powder-soft sands, aquamarine waters, and flavors that dance on the tongue create an unforgettable voyage.

Top Winter Sailing Destinations

The Bahamas – Pristine beaches, secret cays, and turquoise waters teeming with marine life.
Mexico – Ancient ruins, vibrant reefs, and a coastline kissed by golden sunsets.
Thailand – Exotic isles, towering limestone cliffs, and markets bursting with flavor.
Antigua – Colonial charm, world-class regattas, and warm trade winds that whisper adventure.
St Martin – French flair, Dutch energy, and the perfect blend of luxury and laid-back island life.

The Bahamas

Perfect for: Beach Lovers & Adventurers

Imagine waking up to the lull of gentle waves, stepping onto deck to see the morning sun set the sapphire waters aglow. The Bahamas in winter is a sailor’s paradise, where steady trade winds guide you from the bustling heart of Nassau to the untouched tranquility of the Berry Islands and the mesmerizing pink sands of Bimini.

December through February is a time of celebration and discovery. The Junkanoo Festival erupts in a vibrant explosion of color and rhythm, while divers and snorkelers find themselves in an underwater wonderland, encountering sea turtles and iridescent fish weaving through coral grottos.

Set sail for The Bahamas for your own adventure; build your quote today and chart a course for beach paradise.

Mexico

Perfect for: Culture Enthusiasts & Marine Explorers

Golden shores, rich history, and the deep blue embrace of the Pacific; Mexico’s coastline is a sailor’s dream in winter. Cruise beyond La Paz to the hidden gems of Quintana Roo, where coral reefs shimmer beneath the surface, or drift along Puerto Vallarta’s enchanting coastline as whales breach in the distance.

Seasonal wonders await. Witness the breathtaking gray whale migration in Baja California, lose yourself in the revelry of Cozumel’s Carnaval, or plunge into the mysterious depths of Mexico’s famous cenotes. Every moment is infused with magic, every sunset a masterpiece.

Plan your Mexican sailing escape. Get a quote today and set sail for the extraordinary.

Thailand

Perfect for: Island Hoppers & Food Lovers

Thailand in winter is pure tropical enchantment. Imagine balmy breezes, jade-green waters, and limestone karsts that rise dramatically from the sea. Beyond the famed shores of Phuket, discover the unspoiled splendor of Ko Chang and the Phi Phi Islands, where hidden lagoons and secret beaches call to the adventurous spirit.

From lantern-lit celebrations during Chinese New Year to the mouthwatering seafood feasts in Phuket’s bustling night markets, Thailand in the winter is a sensory paradise. Glide over glassy waters, feast on spicy curries by the shore, and dive into a world of dazzling marine life beneath the waves.

Step into Thailand’s tropical dream by building your quote to the exotics today.

Antigua

Perfect for: Regatta Enthusiasts & History Buffs

With steady trade winds and warm waters, Antigua is a dream destination for winter sailing. Beyond the main island, the volcanic beauty of Montserrat, the untouched charm of St. Kitts & Nevis, and the emerald jungles of Guadeloupe beckon.

Winter is the season of spectacle in Antigua. Watch world-class yachts compete in the thrilling Superyacht Challenge Antigua, step back in time at Nelson’s Dockyard, or walk along beaches where sea turtles nest beneath a starlit sky. With every gust of wind, adventure calls.

Visit Antigua this winter; get a quote today and sail into an unforgettable experience.

St Martin

Perfect for: Cosmopolitan Explorers & Anglers

The allure of St Martin lies in its contrasts: French sophistication meets Caribbean charm, and every bay tells a different story. Whether exploring the stylish marinas of Marigot or the lively Dutch quarters of Philipsburg, this island offers a voyage of indulgence and adventure.

Winter transforms St Martin into a sailor’s playground. The Heineken Regatta brings electrifying competition to its waters, gourmet festivals offer a symphony of flavors, and deep-sea fishing excursions promise thrilling encounters with mahi-mahi and wahoo. For those seeking luxury and lively island culture, St Martin is unparalleled.

Discover St Martin’s coastal wonders. Build your quote today and sail into a world of endless possibilities.

FAQs

Can you sail in winter?

Yes, you can sail in winter, and some of the world’s most stunning destinations are at their best during these months. From the Caribbean’s gentle trade winds to Thailand’s sun-drenched isles, winter sailing promises warm breezes and perfect conditions.

Which parts of the world are best for winter sailing?

Parts of the world that are great for winter sailing include the Caribbean, Thailand, Mexico, and the South Pacific. These regions offer golden sunshine, steady winds, and unforgettable coastal scenery from December to February.

Where can you sail all year round?

You can sail all year round in tropical destinations such as the Caribbean, Thailand, and the South Pacific. With consistent warm weather and calm seas, these locations can have ideal sailing conditions no matter the season.

Embrace New Change with The Moorings

Ready to escape the winter blues? Set sail with The Moorings and explore the best winter sailing destinations, from the Caribbean to the South Pacific.

Our expertly maintained fleet and carefully crafted itineraries ensure that your escape is seamless, luxurious, and utterly unforgettable.

Choose from bareboat, skippered or crewed charters so you can pick the right sailing vacation that suits your experience, destination, and how much you want to sit back and relax.

EXPLORE OUR DESTINATIONS