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What makes the Caribbean yacht season stand apart from other destinations?
“Chartering in the Caribbean is unique, you can’t help feeling you’re off the grid in most parts. As a destination it’s just the tonic for those looking to hit the reset button with family and friends. The waters are warm and the nights are humid, perfect for spending time in the water and dining alfresco. Visually beautiful - the islands are green and lush, the definition of tropical, and the sand is clean and white. It’s easy to find secluded bays that provide both peace and privacy,” Shares Bianca.
It’s this mix of ease, beauty and freedom that makes the Caribbean season so sought after and so unlike anywhere else.
When to Go
For Bianca, timing is everything.
“Approximately the end of Dec to the end of March is the perfect time to visit. Drier and less humidity than the summer months. If you’re sailing, the trade winds are steady and consistent at this time of year, hence why the famous St Barths Bucket is held in March each year.”
Our advice: mark your calendar now.
Island-Hopping: The Highlights
From the well-trodden to the wonderfully remote, the Caribbean has a rhythm all of its own. Bianca paints the picture:
“From top to bottom the BVI offer a buffet of islands all very close together making your charter rather sheltered from inclement weather, the Leeward islands are staples and well-visited with a balance of shore-side activities and restaurants, and you move into the Windwards Islands you feel a shift, these mountainous islands are less developed. This is where you can find rainforests and waterfalls. Further down in the most southern part of the Caribbean lie the ABC islands with their own identity; blue waters, flamingos, and colourful picturesque streets.”
It’s a beautiful rainbow coloured spectrum: lively beach clubs in St Barths, rainforests in St Lucia, pastel-coloured streets in Curaçao.
“You can’t help feeling you’re off the grid”
Sailing vs Motor: Two Ways to Charter
“Sailing is a lifestyle, an exhilarating daily activity that charterers consider sport. For those wondering if they should try it, my answer is yes. The luxury elements are all there — you’re just a touch closer to the water.”
Motor yachts, of course, offer more space and size. But for many, Caribbean sailing charters, with steady trade winds and easy distances, are the purest way to experience the region.
Hidden Treasures
The Caribbean still has secrets to share. Bianca shares one of her all-time favourite locations:
“Sandy Island is a hidden gem two miles off Anguilla. You can walk across it in ten minutes. There’s no dock — you arrive by tender, jump off the bow and wade ashore. When you get there, it’s just wooden benches, grilled seafood and a bucket of local beers. It’s the polar opposite of your superyacht — and that’s what makes it so endearing.”
Moments like this are what keep even the most seasoned guests coming back.
Life Onboard & Ashore
The Caribbean season is as much about what happens on board as what happens on shore.
“The yacht provides far more entertainment than you think – the crew are trained in organizing fun for all age groups and profiles. Think private beach set ups with alfresco cooking and fresh cocktail mixing, water Olympics off the stern of the yacht, sailing lessons, fishing, theme nights, white parties, djs and karaoke, and open-air cinema. Shore side, depending on where you are, you can experience fine dining to treks into the rainforest, plus lots of cultural history.
In other words: you’ll never be short of options. At Y.CO we are all about curating extraordinary experiences. We tailor bespoke itineraries, crafted for you.
Top Yachts for the Caribbean Season
Y.CO has standout charter options across the Caribbean here are some of the best — each with its own character, all with exceptional crews.
“All these vessels differ immensely in aesthetic and size. One thing they all have in common are their exceptional charter crew. The crew are the heartbeat of any charter.”
Planning Ahead
“Peak dates for the Caribbean will always be Christmas and New Year. Demand is high, and rates are at a premium, so booking early is highly recommended. But if you don’t have the luxury of advanced planning, don’t be put off — you can still pick up high-season charters in December. Just be ready to move fast.”
The Perfect First Charter
For Bianca, the Caribbean is the ultimate introduction to yachting:
“It’s easy. After touching down from your flight, you can slip onto your yacht in no time. The water is warm and clear, fresh seafood and tropical fruits are abundant. Chartering in the Caribbean offers an ultimate freedom to cruise and move unrestricted. If you enjoy sailing you’ll find it here, if you enjoy privacy you’ll find it here. As a destination it’s unpretentious and offers something for everyone.”
From St Barths’ champagne-fuelled New Year’s Eve to Anguilla’s barefoot bars, from rainforest treks to theme nights under the stars, the Caribbean yacht season has it all. Whether you’re new to yachting or a seasoned traveller, there’s no better place to start your next adventure.
