The Fort Lauderdale International Boat Show closed on November 1, and the Atlantic hurricane season officially ends on November 30, according to NOAA. For anyone planning time on the water this winter, that makes now the moment to turn show-floor conversations into a real itinerary. Paramount’s charter desk focuses on three Caribbean cruising grounds: the British Virgin Islands, St. Barts and the Bahamas. Here is how they differ, and how to plan each one.
Three cruising grounds for the Caribbean season
1. The British Virgin Islands: short hops, many anchorages. The BVI suit a charter that moves a little every day. You can spend the morning among the granite boulders and grottoes of The Baths on Virgin Gorda, snorkel the Caves at Norman Island in the afternoon, and anchor off White Bay on Jost Van Dyke for a sundowner at the Soggy Dollar Bar. Divers can add the wreck of the RMS Rhone off neighbouring Salt Island. Farther out, Anegada is known for its lobster, long beaches and flamingos. The season also has its own social calendar: the 15th annual Necker Cup, a pro-am tennis week on Necker Island, runs November 29 to December 4, 2026. What to do: list the two or three stops that matter most to your group, and let the crew build the daily route around wind and anchorage conditions.
2. St. Barts: the harbour is the destination. A St. Barts charter is less about covering distance and more about time ashore. Gustavia’s harbour puts boutiques and restaurants within a short tender ride, and the island’s beaches and coves are close enough to visit by day and return to town for dinner. In March, Gustavia hosts the St Barths Bucket, an invitational regatta for cruising yachts of 30.5 metres and over, scheduled for March 17 to 21, 2027. What to do: if you are aiming for the holiday weeks or Bucket week, start the conversation early so your specialist can compare yachts while there is still a choice.
3. The Bahamas: shallow water and short distances from Florida. The Bahamas reward a yacht that can get close. Much of the appeal is in clear, shallow anchorages and sandbars, which is why draft matters as much as length when you choose a yacht. Their proximity to South Florida also makes them a natural first charter for clients based in Miami or Fort Lauderdale. Our January story, An Exumas Escape, covers the kind of private-island experience the Exumas are known for. What to do: tell your specialist which islands and beaches you want to reach, and ask about each shortlisted yacht’s draft and tender before you compare prices.
Choosing the right yacht and budget
Paramount’s charter desk works from a framework rather than a price list. Entry Luxury charters run from $40,000 to $100,000 per week and cover refined sailing and motor yachts for intimate trips. Premium charters run from $100,000 to $300,000 per week, with full-service crews, formal dining and water toys. Ultra Luxury charters run from $300,000 to more than $1,000,000 per week, on superyachts with helicopter pads, beach clubs and private chefs. Final pricing depends on the yacht, the season and the itinerary.
For the Caribbean, the yacht type matters as much as the tier. Catamarans offer wide, stable decks and shallow drafts that suit the BVI and the Bahamas. Motor yachts cover longer distances between islands faster. A specialist can help you weigh both against your guest list and route. What to do: start with the number of guests and cabins you need, then the places you want to reach, and set the budget tier last.
Charter first, then decide on ownership
A winter charter is also the best test drive there is. A week aboard shows you how a layout works with your family or guests, what kind of crew you like, and which cruising grounds you would return to. Kaitlin Stoeppelwerth of our charter team sums it up in three words: explore, experience, then own.
That experience also tells you how much time you really want on the water. In our look at yacht ownership vs. charter, we explain why chartering is usually the better fit for a week or two a year, and why the numbers begin to shift toward ownership once personal use reaches four weeks or more. For buyers who want Caribbean time without owning a whole yacht, our Sunreef 80 half-share in Miami offers 26 weeks a year, with a Mediterranean and Caribbean seasonal cruising programme available.
How to plan your winter charter with Paramount
Send us your preferred dates, the number of guests, the islands on your list and the experience you want: active days in the BVI, long lunches in St. Barts, or beaches in the Bahamas. A Paramount charter specialist will respond personally within 24 hours with curated options. As our charter page puts it, a charter is not booked. It is composed.
Charter pricing tiers are indicative. Final pricing depends on yacht, season and itinerary. Event dates are as published by the organisers and may change.
Talk to Paramount Yachts
Whether you are planning a week in the islands or weighing charter against ownership, our charter team will reply to you directly.
Call or WhatsApp: (305) 321-2582
Charter enquiries: kaitlin@paramount.yachts
Office: 1001 SE 17th St, Suite 101, Fort Lauderdale, FL 33316
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