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Yachting holidays: Caribbean destinations for a winter luxury yacht charter

If the cool Autumn breeze on your neck already has you longing to return to summer, then a Caribbean luxury yacht charter is just the remedy you seek to escape the dreary Winter months to come. From November through to March holidaymakers from across the world make the Caribbean their playground, indulging in the riot of colour to be found above and below the waves. Dance on the golden beaches, learn about local history and discover the creative talent of the region as you move from island to island. Whether you prefer wild celebrations or quiet contemplation, the Caribbean has it all. Seek it out by starting with these choice destinations, and find your own favourite hideouts as you roam wherever you please.

Turks & Caicos Islands

The secret has long been out about the Turks & Caicos Islands, which is why if you want to enjoy its splendour without the stress of crowds, a yacht is essential for getting around.

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Relax and reconnect with nature through amazing wildlife encounters and beautiful white sand beaches, and make use of your talented crew to provide all the refreshments and meals while you cruise to bonefishing sites and brilliant coloured reef walls teeming with tropical fish. Of note is the Turks Island Passage – an underwater trench used in the first quarter of the year by migratory species including dolphins, turtles and humpback whales. The impressive snorkelling and Scuba diving sites vary from brightly coloured coral reefs and cliff walls to caverns and shipwrecks such as the HMS ENDYMION at Salt Cay – plenty of choices to keep you occupied all day long.

Wildlife lovers have even more to see close by; The Bahamas is just up to the northwest and the Inagua Islands are home to more than 140 native and migratory birds, many unique and eye-catching with their vibrant plumage.

US Virgin Islands

A three-hour cruise from Fort Lauderdale will have you sipping cocktails in the US Virgin Islands – a destination that has it all. Shopping, fine dining, casinos and nightlife contrast with historic sites such as Blackbeard’s fort and sugar plantations, national parks for hiking, biking and wildlife watching, plus an ‘underwater trail’ for snorkellers to commence at Trunk Bay.

The US VIs have Scuba diving sites for all skill levels, and Frederiksted Pier and Cane Bay are considered among the world’s best dive sites. Be sure to take your underwater camera and make time to be enchanted by these underwater wonderlands.

The British Virgin Islands

Both the US VIs and the BVIs are top destinations for winter luxury yacht charters, particularly around the festive season. Foxy’s Bar and Soggy Dollar Bar on Jost Van Dyke are known for their New Year’s Eve parties, which attract many a yacht to their bays to see out the old year in style.

The Little Sisters is a cluster of islands well worth your attention, with excellent spots for sport fishing, quiet beaches and the Rhone Marine Park, the site of the most famous shipwreck in the Caribbean.

The Baths on Virgin Gorda has a unique beauty perfect for memorable family photos and your social media. For another sensory feast, try the local rum produced at the Callwood Rum Distillery on Tortola, shop and visit the museums in Road Town, and head to Smuggler’s Cove for a panorama of golden sands and turquoise blue sea.

Saint Barthelemy

With Anguilla and Saint-Martin/Sint Maarten to the north and Saint Kitts & Nevis to the south, Saint Barthelemy is ideally situated for an island-hopping itinerary of shopping, socialising and fine dining. Saint Barth is most famous for its regatta, Saint Barth’s Bucket.

This multi-day event displays the prowess of modern and traditional sailing yachts across various categories, with the next regatta due to take place on 15th-19th March 2023. The bays around the island offer up large crescent beaches and quiet anchorages for a tranquil night’s rest.

Saint Lucia

The Pitons are the star attraction on Saint Lucia, and as you hike the trails to the top for the impressive vista, you’ll encounter the native flora and fauna, waterfalls and mineral baths and mud baths that’ll tempt you on your descent. Pigeon Island National Park offers up more beautiful hiking spots and historic sites, and the beaches along the eastern shores await candlelit dinners beside the sea.


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Epicures in your group will delight at the fresh offerings of the ‘Spice Island’, which supplies the world with nutmeg, cinnamon, turmeric and more grown for its fertile soil. Supply your own supper through a fishing expedition, and let your professional chef bring out the best flavours of your catch.

To balance out all the amazing feasts, Grenada has excellent conditions for wind-powered water sports, whether it’s sailing in a dinghy, windsurfing or kite-surfing around the bays. When all your energy is spent on water sports, unwind on the warm white sand beaches and simply let time carry on.


Although technically part of South America and not the Caribbean, Belize shares its borders with Mexico and Guatemala, the former is another popular winter charter destination due to its golden sand beaches and impressive cultural attractions to be found in Quintana Roo and Yucatan.

Belize boasts its own treasures, most notable status as a UNESCO World Heritage Site for the world’s second-largest reef system. Turneffe Atoll is a prime destination to spot reef sharks and sea turtles while Scuba diving and Half Moon Caye has a range of snorkelling and Scuba diving sites for all experience levels, along with a world-renowned 127m/416ft deep blue hole. Lastly, the 400+ islands all but guarantee you an anchorage all to yourselves to savour sunny afternoons and starry night skies without distractions.

Luxury charter yachts vary in size and amenities to suit budgets of all sizes, from intimate family-sized catamarans to no-expenses-spared mega yachts. Plan your dream Caribbean escape and indulge stress-free this winter in a tropical paradise of your choosing.

Trina Howes is a Director of CharterWorld America. CharterWorld is a luxury private yacht charter company that creates outstanding vacations with excellent yachts at amazing prices – worldwide.

If you would like to be a guest blogger on A Luxury Travel Blog in order to raise your profile, please contact us.

Trina Howes

Trina Howes is a Director of CharterWorld America. CharterWorld America is a luxury private yacht charter company that creates outstanding vacations with excellent yachts at amazing prices – worldwide. If you would like to be a guest blogger on A Luxury Travel Blog in order to raise your profile, please contact us.

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    1. Thank you, yes the possibilities are endless. The nice thing about a private luxury yacht charter is the complete personalization of your itinerary and the ability to move from place to place without having to pack you luggage.

  1. Heading to the Caribbean to cruise around the islands and escaping the icy blast of a UK winter really has to be the ultimate dream. I can see it bring a tough winter here in Blighty heading into another Winter of Discontent with the threat of power cuts.

  2. There is nothing worse than living out of a suitcase. I’ve done it for so many years for work that I hate doing it when I travel for pleasure.

    The excitement of new places is one of travel’s things for me, if I can get over all the packing and unpacking then I’m on to a winner.

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