Last Updated on November 28, 2023

Many of us dream of getting away from home during the cold winter months and having a week or two of blissful sunshine. Better yet, when that sunshine is enjoyed from the water.

Kate Kalamaga, founder and owner of Tropicalboat Luxury Yacht Charters & Rentals, has compiled her list of favorite sun and sea destinations. Bon voyage!

#1 Saint Martin Island

Average winter temperature: 28 degrees Celsius

Saint Martin is a true aquatic paradise, beckoning all water enthusiasts to its stunning shores. This island is renowned for its collection of 37 picturesque beaches, each graced with powdery white sands and crystal-clear turquoise waters. It’s an ideal haven for those who cherish sailing, offering an excellent spot to drop anchor and test your seafaring skills in the boundless expanse of the open sea.

As the hurricane season concludes in November, the winds shift to a southeasterly direction, typically blowing at a gentle 10 to 15 knots. This transition makes it the perfect window of opportunity for a sailing adventure.

#2 Belize

Average winter temperature: 24 degrees Celsius

Being home to the world’s second-largest coral reef, means Belize stands out as a true gem. Yet, the allure goes beyond its breathtaking coral formations. Here, you have the privilege of standing with one foot on a powdery white beach and the other in the midst of Central America’s rainforests.

Sailboat captains are particularly enamored with Belize for its consistent, temperate trade winds that grace the region year-round, creating ideal conditions for navigation. With the added advantage of line-of-sight sailing, the experience is made even more enjoyable.

#3 Sicily

Old wooden fishing boats on the beach of Cefalu, Sicily.
Old wooden fishing boats on the beach of Cefalu, Sicily. Photo by Deposit Photos.

Average winter temperature: 14 degrees Celsius

If you found yourself engrossed in the fantasy world of “The White Lotus,” you can embark on a mesmerizing journey through the same landscapes as the cast of the second season by visiting Sicily during the off-season. Winter on the island unveils its own vibrant charm, as people prepare for the spirited celebration of Carnevale.

Sicily offers a promise of more sandy shores, abundant sunshine, and hidden anchorages than you can imagine. The real yachting gem here is the Aeolian Islands, a cluster of seven subtropical isles and numerous volcanic specks that beckon both Italian A-listers and humble fisherfolk alike.

#4 Cape Verde

Average winter temperature: 23 degrees Celsius

Nestled approximately 350 miles to the west of Senegal, the Cape Verde archipelago experience is enriched by continuous sunshine and a constant, invigorating breeze, usually blowing at a moderate force 4-7.

This archipelago is a sailor’s dream, featuring a mix of islands, some spaced as far as 100 miles apart, while others are only a half-day’s sail away. It’s an unparalleled cruising destination for those seeking secluded anchorages and islands to explore without the crowds of tourists.

In addition to sailing, Cape Verde offers a range of exciting activities. Surfing enthusiasts can ride the waves, and from February onwards, the seas become a prime spot for whale-watching.

#5 Phuket & the Similan Islands

Average winter temperature: 24 degrees Celsius

Embarking on a yacht-charter adventure in Thailand begins with the picturesque Phuket, the country’s largest island. Prepare to be mesmerized by the enchanting topaz waters of Phang Nga Bay that maintain their inviting warmth throughout the year.

For those seeking the ultimate Treasure Island experience, a voyage to the Similan Islands is a must. This pristine archipelago, consisting of 11 islands, is located approximately 100 kilometers (62 miles) to the northeast of Phuket and is nestled within the protective embrace of a national park.

Accessible from November to April, scuba divers, bird enthusiasts, and beach lovers alike will be captivated by the Similan Islands’ charm.

#6 Tobago

Average winter temperature: 22 degrees Celsius

Nestled in the heart of the Caribbean, Tobago is blessed with breathtaking natural beauty and a vibrant local culture that fills the air with energy. The tranquil waves gently caress pristine, ivory-white sandy beaches, creating an idyllic setting. Its exceptional marinas and strategically sheltered locations make it a perfect destination for an extended stay.

In addition to secure mooring options, Tobago offers world-class repair facilities, presenting boat owners with an opportunity to combine a stopover with essential servicing, ensuring a safe and enjoyable journey.

#7 Athens

Ancient theatre in Acropolis; Athens, Greece. Photo courtesy of Deposit Photos.
Ancient theatre in Acropolis; Athens, Greece. Photo courtesy of Deposit Photos.

Average winter temperature: 14 degrees Celsius

Embarking on a sailing adventure from Athens presents a unique opportunity to immerse yourself in both the rich cultural history of the Greek capital and the unspoiled splendor of the Greek islands.

Situated just a short sail away from the bustling port of Piraeus, the islands of the Argo-Saronic Gulf hold a special place in the hearts of sailing enthusiasts, cherished for their serene ambiance and natural wonders.

Navigating the southern coast of the Attica peninsula is particularly appealing to those with less sailing experience, as the expansive bay provides a shield from strong winds and turbulent waters, ensuring a smoother voyage.

#8 Corsica

Average winter temperature: 17 degrees Celsius

Corsica, the Mediterranean’s fourth-largest island, beckons with its 1,900 kilometers (1,200 miles) of picturesque coastline, a realm best explored by sea. While Corsica has been under French sovereignty since 1768, it retains a distinct Italian charm, with enchanting medieval ports that exude timeless beauty.

Beyond its cultural allure, this island boasts unspoiled natural reserves, a culinary scene that is nothing short of excellent, and reliable winds that propel your seafaring adventures.

Here, you’ll discover a plethora of idyllic anchorages, sleepy fishing villages, and secluded beaches accessible exclusively by boat.

#9 Tenerife

View of Las Teresitas Beach, Tenerife, Spain
View of Las Teresitas Beach, Tenerife, Spain. Photo by Deposit Photos.

Average winter temperature: 16 degrees Celsius

Tenerife, the largest of the Canary Islands, stands as a prominent sailing hub in Europe, drawing over 10 million tourists annually to its shores.

It offers a wealth of sailing itineraries, each promising a remarkable voyage. Here, you can relish exceptional sailing conditions, first-rate marinas, and premium anchorage spots. The island’s weather conditions are idyllic for sailors of all skill levels, thanks to the consistent North-Easterly trade winds associated with the anticyclonic Azores.

#10 Sardinia

Average winter temperature: 15 degrees Celsius

Sardinia is a beach lover’s paradise, boasting an astonishing 200 of them waiting to be explored. What makes Sardinia even more appealing is the seclusion of its coastline. While the island is a haven for tranquility and natural beauty, it welcomes a modest 3.4 million tourists each year.

To put this into perspective, Mallorca, which is just an eighth of Sardinia’s size, hosts more than 10 million visitors annually. This disparity leaves the pristine tiny islets, snorkeling paradises, and secret anchorages for you to savor, offering an exclusive and unparalleled coastal experience.

Author

  • Chadd Scott

    Chadd Scott is an arts contributor with Forbes and the founder of See Great Art, where he writes about his travels from big city museums to small town galleries in search of great art.

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