On unknown or famous islands, between art and nature, you are spoiled for choice. So we chose in a real journey around our Top 50 where to sail this winter. It starts from the Caribbean and other North American destinations!

Antigua

A great classic that really never seems to go out of style. The island is part of the Antilles, and the sea temperature is between 26 and 28 degrees. In addition, constant cool trade winds blow there, allowing average temperatures to rarely exceed 30 degrees between December and March. So many must-see destinations, not to mention white beaches that you won’t even be able to count. Don’t forget the decadent Fort James, dating back to the 1700s, which will propel you into the English past. Learn about the best rental offerings.

Bahamas

As many as seventy islands and islets make up this archipelago discovered by Christopher Columbus. The two white sand beaches best known to travelers are the spectacular Cable Beach and Cabbage Beach. However, if you are headed to Big Major Cay Island, you will find a beach where a dozen friendly piglets live and allow themselves to be photographed by tourists. Learn about the best rental offerings.

Belize

Discovering Belize by sailboat is an incredible experience, just think that the second largest coral reef in the world after Australia’s is located here. And once you have immersed yourself in the turquoise waters of the most remote cayes, if you love history in Belize you will find some of the best-preserved ruins in the world. Among them undoubtedly the site of Caracol with its 43-meter-high pyramid. Learn about the best rental offerings.

Bermuda

Bermuda appears, at first glance, to be a single island, but it is actually composed of 181 islands, islets and reefs. Surrounded by turquoise sea and dotted with coral reefs, it is a sanctuary that is home to extraordinary marine life. Known as the diving capital of the North Atlantic, Bermuda is surrounded by more than three hundred shipwrecks, some dating back to the 17th century, just waiting to be explored. Learn about the best rental offerings.

British Virgin Islands

Elegant yet simple, a must-do stop, at least once in a lifetime, for every self-respecting sailor. Sailing along the Drake Channel, amidst the islands that were once pirates, is a spectacle. The islands are very diverse, from the capital city of Tortola to elegant Virgin Gorda to the simpler Jost Van Dyke, where Foxy’s beach bar holds weekly sailor nights, which drop anchor in the bay in front. Learn about the best rental offerings.

Channel Islands

An ideal destination from November through April, this archipelago consists of eight islands in front of Southern California and San Diego, which can still rely on year-round temperate weather. During the winter, the very hot Santa Ana Wind often blows. In the spring it is the perfect place to witness the incredible spectacle of passing whales and orcas, while the waters are inhabited by sea lions, dolphins and sharks. Learn about the best rental offerings.

Florida Keys

The Florida Keys (Spanish for Cayos de la Florida) are an archipelago of about 1,700 islands in the southeastern United States and extend in a gentle arc from northeast to southwest to Key West, the westernmost of the inhabited islands, and Dry Tortugas (uninhabited). The last place you would expect to find only fifteen miles from chaotic Miami. That is also why they are even more fascinating. Learn about the best rental offerings.

Guadeloupe

Guadeloupe is the largest island in the Lesser Antilles, actually formed by two islands separated only by a narrow natural channel, the so-called Rivière Salée, a 5-kilometer-long arm of the sea. Its extremely rich marine life, with extraordinarily colorful fish and crustaceans, as well as corals, of course, makes it one of the cult destinations of diving enthusiasts. Learn about the best rental offerings.

Isla Holbox – Mexico

On the northernmost tip of Mexico’s Yucatan Peninsula, separated by the shallow Yalahau Lagoon (by the way, what a sight the flamingos are here) lies this island far from the stresses and rhythms of modern life. The best time to choose this little paradise is from November to May, and many charter companies offer a cruise here. Our advice is to tie it in with a more cultural itinerary to discover the Mayan ruins scattered throughout the Yucatan Peninsula or the nightlife of Cancun. Learn about the best rental offerings.

Havana – Cuba

Colorful, contradictory, fascinating and a thousand other adjectives we could use, all for one place: Havana, the symbol of Cuba. Its historical, architectural and cultural heritage, expressed by the fusion of Europeans, Africans and Aborigines resulted in its historic center being declared a UNESCO World Heritage Site in 1982. With the end of the U.S. embargo, great changes are expected. All the more reason to go immediately to see it, a great starting point for navigating around the island. Learn about the best rental offerings.

Nicaragua

One of the most fascinating states of Central America is definitely Nicaragua: the charm of these places is due to the particular location of this state that is bathed by the Pacific Ocean and the Caribbean Sea and contextually, thanks to a particularly lush nature offers unmissable landscapes with lakes, forests and volcanoes. Don’t miss the two Corn Islands (large and small), a true Caribbean paradise where you can snorkel and dive. Learn about the best rental offerings.

Puerto Rico

Avoid the poorly sheltered northern coast and aim south instead. There are many beautiful reef-protected beaches here, with warm and calm water, so suitable for calm swimming and snorkeling; the most recommended are Punta Guilarte Beach (near Arroyo) and La Parguera, which is very famous and called “fluorescent bay” because the presence of aquatic microorganisms generates the phenomenon of luminescence at night. Learn about the best rental offerings.

Dominican Republic

On one of the Caribbean’s most beloved islands, set the bow south to Barahona, considered the true center of Caribbean ecotourism. White beaches and vibrant, colorful marine life make it an ideal destination for a “natural” cruise. If, on the other hand, you are looking for a convenient and safe place to stop and refuel, aim for the Casa de Campo marina in La Romana, which is located on the Salao River. In fact, many local craft stores and large supermarkets are within walking distance from the West Pier. Otherwise, one can opt for Catalina Island, located southwest of the port of La Romana, which has no actual port but a protected docking system. Learn about the best rental offerings.

Saint Kitts

It is probably the Caribbean island that has experienced the most development in the area of nautical tourism in recent years. A perfect example is the brand new Christophe Harbour along the south coast, dedicated to large yachts. Don’t worry, there are dozens of bays where you can enjoy an unforgettable cruise. Learn about the best rental offerings.

Grenadines

Among the many archipelagos of the Lesser Antilles. this is undoubtedly the one that has managed to retain its natural beauty and simplicity. A feature always appreciated. Learn about the best rental offerings.

San José del Cabo

Not to be confused with the better-known Cabo San Lucas, a destination for rowdy tourism, this small town instead makes calm and tranquility its strengths. This is done by alternating between stops at roadsteads in front of endless white beaches and walks through old village streets. Learn about the best rental offerings.

St. Petersburg

Often held in low esteem, overlooked by glitzy Miami, this Florida city is instead experiencing slow but gradual growth, both in terms of its social life and accommodations, including ports. Learn about the best rental offerings.

Todos Santos – Mexico

Another pearl of Baja California, it was once the “buen retiro” of surfers from around the world and is now becoming known not only for the natural beauty of the coast but also for a vibrant artistic activity. Once off the boat, rent bicycles and embark on one of the many routes that have been organized in recent years to discover villages located a few kilometers inland. Learn about the best rental offerings.

Vinales – Cuba

If you are sailing to explore the island of Cuba, one stop we recommend once you get ashore involves the Vinales Valley. A UNESCO World Heritage Site, it is said to have been Fidel Castro’s favorite place, with its tobacco crops (said to be the best in the world) and quaint villages where the rhythms of life are still those of decades ago. Learn about the best rental offerings.

Yucatan – Mexico

Few regions in the world have as much wealth and tourism as Mexico’s Yucatan Peninsula. White beaches and palm trees, azure waters and lush bays for unforgettable nights at anchor, but also bustling nightlife and, moving inland, Mayan ruins. Learn about the best rental offerings.

NOW FIND THE RIGHT BOAT FOR A CARIBBEAN CRUISE

DISCOVER ALL THE TOP 50 DESTINATIONS IN THE DECEMBER JANUARY ISSUE OF THE JOURNAL OF SAILING, ON NEWSSTANDS AND DIGITAL STARTING DEC. 1