Winter is considered to be the best season to charter a yacht in the Caribbean and many other beautiful tropical locales. A winter sailing holiday offers the ultimate in freedom and independence. If you want to experience the ocean breezes and refreshing cocktails while cruising at your own pace on a stylish yacht, consider one of these 8 tropical destinations.
The British Virgin Islands
Picture sailing in a tropical paradise with over fifty islands waiting for you to discover. Imagine lounging on white-sand beaches under vivid blue skies while a balmy Caribbean breeze caresses your skin. Or perhaps, dining beach-side while enjoying an enchanting view of the winter sun setting over the horizon. The BVI may sound magical, but words don’t do this Caribbean paradise justice.
These islands are the epitome of tropical luxury. It’s a place where you can unplug and lounge oceanside while enjoying Caribbean hospitality, serene 82-degree weather, and a selection of fine dining establishments right on the beach. The lively party atmosphere only heightens after the sun sets, and you can revel in live music on the beach in Tortola or treat yourself to a revitalizing beach-side massage at Leverick Bay Spa.
The entertainment is endless, but the unspoiled islands are also full of hidden treasures. From the tucked-away coves of Norman Island to the Baths of Virgin Gorda Island (a labyrinth of boulders on the beach) to Tortola, a yachting destination full of lush scenery, sensory delights, and blissful privacy, you have several beautiful locations to explore on your own, with your partner, or as a group.
Places to Visit in the British Virgin Islands
- Norman Island: Do you want to be a real pirate of the Caribbean? You can at Norman Island, famously known as a graveyard for shipwrecks. Immerse yourself in the warm waters and explore the intriguing marine life the island has to offer.
- Cooper Island: Cooper Island offers one of the many snorkeling locations around the islands, so you won’t want to miss making an excursion or two into the turquoise waters to experience the colorful coral and tropical fish up close and personal. Afterward, head on over to Cooper Island Beach for some fine-aged rums and 5-star cuisine under the warm Caribbean night.
- Jost Van Dyke: If you’re here to party, enjoy sandy beaches, and lounge at beach-side resorts, Jost Van Dyke is the place to visit. Anchor near the beach to savor the great food and beverages, and if you can spare some time, swim your way to the Soggy Dollar Bar for a drink and some music.
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St. Martin
The charming island of St. Martin is a hot spot for sun, sand, and world-class cuisine from two different cultures. The tiny island is a delightful destination for tourists, adventure seekers, and luxury shoppers.
Surrounded by Tintamarre, Anguilla, and St. Barts, vacationing in St. Martin offers you a rare blend of Caribbean culture, European luxury, and tropical island vibes. For instance, Anguilla’s coastline is a mostly rugged rock with several white-sand beaches, but St. Barts’ is dotted with luxury mega yachts and high-end shopping establishments. The locals tie it all up together with their friendly Caribbean charm, and in case you forget where you are, the stunning panoramic views of the sea at several resorts and restaurants will quickly remind you.
Sumptuous aromas greet your senses once you venture a short distance in-shore. In Grand Case, piles of grilled chicken and ribs sizzle invitingly at the “Sky’s the Limit” lolo, right next to the dock. The portion sizes are enormous, and each dish bears a delicious Caribbean flair. Or, if you prefer a little more privacy, the uninhabited Tintamarre Island is a bird and turtle-spotting sanctuary with quiet beaches where you can enjoy a tasty grilled dinner in the amber glow of the setting sun.
Places to Visit in St. Martin
- St. Barts: Once you dock at the Gustavia harbor, a short stroll will bring you to Shell Beach, the best place to spend a Sunday in St. Martin. It’s a cliff-side beach with electric blue waters below, but apart from the stunning vista, you can dine in the posh Shellona restaurant and feast your eyes on models as they strut luxury items at the adjacent boutiques.
- Grand Case: Situated west on the French northern side of St. Martin sits the dazzling Grand Case cove. The Baie de Grand Case features stunning vibrant blue waters and exceptional Caribbean snorkeling and diving. This magical wonderland is best known for is its exquisite Creole and French cuisine. Feast like kings and queens at one of the many fine dining restaurants at “The Gourmet Capital of the Caribbean,” like the Bistrot Caraibes or La Villa. Then, sail to the reef at Créole Rock to watch the sunset at one of the best spots to bid the evening adieu.
Winter in St. Martins is a busy period full of events and celebrations. February brings along “Mardis de Grand Case,” a parade that runs for a few months, filling the little islands with music, treats, and streets of dancing locals and tourists.
In March, the Heineken Regatta, a 4-day racing competition for boats worldwide, fills the beaches with action and endless entertainment to go with the exquisite cuisine and refreshing beverages. It’s a seasonally busy time of the year for the locals, but for you, it will be an experience to remember.
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Puerto Rico
Covering just over 270 miles of coastline, Puerto Rico is one of the best winter sailing destinations you don’t want to miss out on. The islands present a blend of natural features, rich culture, delicious cuisine, colonial architecture, and white, sandy beaches bordered by luscious mangroves. The region also hosts the popular Spanish Virgin Islands – Vieques and Culebra, as well as many sheltered coves and islets perfect for exploring.
Aside from world-class sailing, Puerto Rico offers miles of coral reefs to explore, surfing, snorkeling, and kayaking, not to mention on-shore activities like bird-watching and hiking. The island’s tropical climate keeps you wrapped in cozy temperatures and warm tropical winter days that make for a magical experience.
Places to Visit in Puerto Rico
- Mosquito Bay: While you’re sailing in the waters of Puerto Rico, Mosquito Bay is a must-see spot you do not want to miss. It’s the brightest bioluminescent bay in the world and provides a magical experience. You will feel like you are drifting on a sky full of stars.
- Puerto del Rey Marina: Known as the largest marina of its kind in the Caribbean, the Puerto del Rey Marina is home to picturesque beaches, lush rainforests, and underwater caves that provide the perfect opportunity to explore the clear waters of the island.
- Bahia del Almodovar: An excellent mooring spot with activities like kayaking, paddleboarding, and snorkeling to keep you entertained. A walk through the mangroves or a quick trip to Culebrita to catch a glimpse of the beautiful Tortuga Beach from a cliff top is the ideal way to end the day.
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Belize
Belize is the home of a 300km-long barrier reef that is a designated UNESCO World Heritage Site due to its diverse marine life. Similarly, the island plays host to various cultures, including Asian, European, Mayan, Creole, and Mestizo.
With a wide array of delicacies, music, and adventures to partake, Belize is a magical land beyond your everyday life, sailing from one beautiful cay to the next while soaking up the Caribbean sun.
Belize has Mayan ruins, scuba diving, and snorkeling spots where you can observe its unique undersea ecosystem in detail. With great weather all year round, it’s a luxurious destination to escape to when trying to beat the winter chill.
Places to Visit in Belize
- The Great Blue Hole: Lying near the center of Lighthouse Reef and located 43 miles offshore of the mainland of Belize, the Great Blue Hole is a giant oceanic sinkhole named for its distinct and intense blue color compared to the turquoise reef waters surrounding it. It formed over the last 150,000 years during several glacial periods when sea levels were much lower. As the waters rose, the cave was flooded and the cavernous ocean cavity we see today was created. The Great Blue Hole now measures over 1,000 feet in diameter.
- Rendezvous Cay: Spend an eerie night on the unreal Rendezvous Cay, an island so small, it looks artificial. Perched atop the rich corals, it is a great place to snorkel and enjoy a starry night sky over a bonfire and marshmallows.
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Bahamas (Sea of Abacos)
The Bahamas cover over 100,000 square miles of ocean with plenty of places to sail, stretching from the east of Miami to the shores of Cuba. Your winter destination awaits at the Sea of Abacos, home to a few of the magical 700 islands that make up the archipelago.
Dock at the capital, Nassau, to explore inlets and enjoy some R&R at one of the luxury resorts on the beaches of Rose Island. The Exumas are only a short journey away from the shoreline should you develop a hankering for some tropical adventure. If not, moor on Paradise Island to explore the beach-side resorts offering Caribbean delicacies, luxury amenities, refreshing beverages, and thriving nightlife.
Places to Visit in the Bahamas
- Green Turtle Cay: If you like beaches, swimming with green sea turtles and sting rays and the island pigs, fishing, and enjoying a cocktail during an island cookout then this is your place. At Green Turtle Cay, you’ll find a nice selection of bays and harbors to choose from for some afternoon relaxation or some sensational snorkeling. Take a walk or drive a golf cart around the island to some of the popular restaurants and shops or to soak in the villages’ rich history and marvelous landmarks.
- Elbow Cay: Boating to Tahiti Beach is a popular destination when sailing to Elbow Cay. This picturesque point of pristine white sand offers the ideal spot for sunbathing and swimming. Snorkeling, scuba diving, and watersports, are also popular activities. Explore Elbow Cay by foot, bike or golf cart and enjoy some shopping, fine dining, and be sure to make a trek over to the famous Hope Town Lighthouse.
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Antigua
With the Atlantic trade winds filling your sails, yachting around Antigua promises to be an exhilarating experience. Anchor on the stunning beaches of this Leeward Island to meet the friendly locals, drink some great rum, and sample the local cuisine, which leaves aromas wafting in the warm tropical atmosphere.
Antigua has some of the most stunning beaches in the Caribbean, a rich culture to get lost in, and plenty of resorts to bring you relaxation. A handful of themed bars keep the nightlife thriving, giving you something to do when you’ve spent all day lounging.
Places to Visit in Antigua
- English Harbor: English Harbor is home to a UNESCO World Heritage Site, calm waters full of diverse marine life and colorful coral reefs for your exploration.
- Green Island: Antigua’s bustling wildlife and tranquil environment is at their best here on Green Island. Carry a pair of binoculars to spot exotic tropical birds, and then head to the local resort for lunch and drinks on the beach.
- Deep Bay: Sunbathe on the outstanding Deep Bay beach while enjoying an unimpeded sea view, a great place to camp out and catch the sunrise.
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Tahiti
Tahiti is a beautiful place and a must-visit destination should you ever find yourself in the waters around French Polynesia. From valleys to volcanic peaks to lagoons, the island has breathtaking beauty all around, and if it’s a feast for your eyes you want, the beautiful landscape and wildlife will satisfy you completely.
While you’re there, explore some of what Tahiti has to offer for entertainment. You can dive and snorkel, or you can stay above water and participate in windsurfing, canoeing, kiteboarding, and hiking.
During the winter, the locals celebrate cultural events like the annual Heiva festival of dance and song. These events promise to make your sailing trip a memorable one.
Places to Visit in Tahiti
- The Coral Garden: Located off of Taha’a and tucked in between two tiny motus runs an entrancing current over a shallow coral reef, creating the iconic Coral Garden. Dip into one of the most captivating snorkeling spots you will find anywhere. You will find an abundance of parrot fish, clown fish, moray eel and giant anemones just under the surface. This is a one-way channel in the sea, so simply dip in and let the gentle current float you along, then stroll back to the start and go again.
- The Society Islands: Explore the rich tropical heaven Tahiti by mooring at the Society Islands. There are fun activities for all types of vacationers, plus beautiful scenery and cultural festivals to enjoy in these volcanic mountains and lagoons.
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U.S. Virgin Islands
Many people have overlooked the USVI in the past, but recently more chartering clients have been vacationing there with extremely positive feedback. Whether you are interested in lots of snorkeling, scuba diving, eating ashore, hiking or just relaxing, the USVI offers a variety of itineraries to meet your expectations!
With short distances, predictable tropical weather, an abundance of water activities and onshore restaurants and bars, the USVI has something to offer everyone! Most sailing vacations start from St. Thomas to explore the main islands of St. Thomas, St. John and Water Island, plus 50 smaller islets and cays.
With so much to do and see in the US Virgin Islands your sailing vacation will be packed with beautiful sightseeing, great food, yummy cocktails, beautiful sunsets, exciting water toys, and a whole lot of fun!
Places to Visit in USVI
- Carvel Rock: Dive the celebrated Carvel Rock and look for old cannon balls and other unique artifacts! You may even be fortunate enough to see some black tip reef sharks that are local to the area! Still feeling adventuresome? Ask the locals about thrilling cliff diving opportunities for a exhilarating adrenaline rush.
- Charlotte Amalie: Check out the 99 steps, Emancipation Gardens, the historic Fort Christian and the famous downtown. Treat yourself to some retail therapy at the many downtown boutiques or at the vendor’s plaza.
- Magens Bay: An unbeatable site for watersports like tubing, wake boarding, and water skiing. Take an afternoon swim at one of the quiet, isolated strips of the beach, and enjoy the gorgeous scenic views.
Blow away those winter blues with a winter sailing holiday to one of our favorite destinations. Cold days and dark nights will be a distant memory. Enjoy the warmth of the sun and the gentle ocean breezes as you cruise some of the world’s most exotic winter sailing destinations around the world… Request a quote today.