The Caribbean and the Bahamas are the hotspot for crewed yacht charters once temperatures drop in the Mediterranean. The region is one our CharterWorld brokers know intimately, from the quietest Exumas anchorages to the liveliest bays of the Leewards – home to St Barths, St Martin and the Virgin Islands. With firsthand knowledge and years of experience, we’re here to share an insider’s view on what’s shaping the 2025/26 season, the yachts to watch, and the experiences that will make your charter unforgettable.
Cruising the Caribbean
Demand Trends: Where Clients Are Heading
Early bookings reveal strong demand for the Leeward and Windward Islands – including St Lucia and St Vincent and the Grenadines, with the U.S. Virgin Islands also drawing interest, particularly among American clients seeking short, convenient getaways. With a smaller fleet available in the USVI, securing the best options takes some forward planning.
The Bahamas, by contrast, has seen a steady softening in demand with the exception of Christmas and New Year which remain heavily booked. There are plenty of opportunities for clients to secure excellent value outside the peak holiday weeks.
Exuma in the Bahamas – meeting the friendly pigs
It’s not just U.S. charterers heading to the region this year – you’ll be joined by European and Asian travellers too, drawn by the Caribbean’s mix of ease and adventure. And while you may not need to book as far in advance as for the Med, it’s also not a last-minute market. Most charters are being arranged a few months out, striking a comfortable middle ground.
The Yachts: Familiar Favourites and Fresh Faces
This season may not be defined by a flood of brand-new yachts, but the fleet remains rich with choice. Standouts include motor yachts ALPHA WAVES and SQUALO, as well as the welcome return of sailing yacht WINDROSE OF AMSTERDAM, a yacht perfectly suited to Caribbean cruising with her relaxed spirit and open-deck lifestyle. Luxury catamaran SHADES OF GREY also joins the line-up.
For family gatherings or festive escapes, smaller catamarans such as EVENSTAR and HUNTRESS continue to prove popular and are a firm favourite of CharterWorld broker Hadley Albanese.
“I would pick EVENSTAR or HUNTRESS for a Christmas or New Year charter with family and friends. I know their crews well, and the charters they deliver are some of the most memorable,” she comments.
On Board and On Shore: How to Spend Your Days
Clients today are looking for more than just idyllic sailing, they want immersion, so Caribbean islands are answering with cultural classes, music workshops, craft experiences, cooking lessons, and guided biking tours. It’s part of a broader shift as guests are leaning towards collecting experiences rather than purchases, layering local discovery onto their time onboard.
Exclusive isolated beaches
Chartering in the Caribbean or Bahamas is a distinctly different experience from the Mediterranean. Where the Med can be a ‘see and be seen’ scene, with tightly managed itineraries and glamorous port calls. In contrast, the Caribbean is more relaxed and flexible, shaped by a leisurely on shore lunch or the simple joy of being out on the water.
The Bahamas, especially the Exumas, epitomise this spirit. “The Exumas are one of the very few places on earth that look exactly like the best brochure photos once you arrive,” reflected Nicolas Benazeth, CharterWorld’s Director of Charter. “Pristine beaches, crystal-clear waters, and easy cruising distances – it’s picture-perfect.”
Hadley adds:
“I think people underestimate how close paradise really is. From the snowy mountains of Montana you can be in the Bahamas’ turquoise waters in less than a day – or enjoy a passport-free week in the USVI. It’s the simplicity and contrast that makes it so special.”
St Barths – the island for luxury ashore
In the Caribbean, you’ll also notice a difference in service style. In the Med, crews often share their culture – Greek captains showing hidden anchorages, or Croatian chefs cooking family recipes. In the Caribbean, the focus is on creating new memories with your friends and family. Expect beach barbecues, movie nights under the stars, and weeks that feel like one long celebration.
Looking Ahead: A Season Full of Promise
The 2025/26 Caribbean and Bahamas season is already shaping up with something for everyone: vibrant itineraries in the Leewards and USVI, peaceful escapes in the Bahamas, and a fleet that ranges from family-friendly catamarans to grand superyachts.
A great choice of yachts
What makes your experience unique is the match between destination, yacht, and crew – and that’s where CharterWorld’s expertise makes the difference. We will guide you toward the right choice, set the right expectations, and make sure your charter becomes the unforgettable escape you’ve been imagining.
Trust our experience – because in yachting, detail is everything.
