Destinations, Caribbean and Bahamas
Yacht Charter in the Caribbean and Bahamas.
Warm winter cruising through the Antilles, the Virgin Islands, and the seven hundred islands of the Bahamas.
English Harbour
Virgin Islands
Gustavia
Mustique, Bequia
The Exumas
SECTION 01
Why charter here
The Caribbean is where the yachting world moves in the winter months. Turquoise water, reliable trade winds, short crossings between islands, and a mix of cultures shaped by centuries of European, African, and colonial influence. For guests who want warm-weather cruising during the northern winter, few destinations rival it.
These are destinations we arrange through our network of trusted partners across the region. Whether the charter is a classic Leewards tour, a week in the Bahamas, or a more focused stay in the Grenadines, we work with the operators best placed to deliver it.
SECTION 02
The cruising grounds
A few considerations worth thinking about before we speak. You don’t need to have everything figured out before reaching out, but these will help shape the conversation.
Destination 01
Antigua and Barbuda
The heart of Caribbean yachting.
Antigua is the central hub of Caribbean charter culture, home to English Harbour and the Antigua Yacht Show, one of the most important events in the winter calendar. The island is small but strategically placed for onward voyages to the Leewards to the north or the Grenadines to the south.
Barbuda, thirty miles north, offers a quieter alternative with some of the longest undeveloped pink-sand beaches in the region.
English Harbour
November to May
Barbuda pink-sand beaches
The Leewards
Destination 02
The British Virgin Islands
Short hops between islands.
The BVI is one of the most easily navigable cruising grounds in the world. More than fifty islands and cays lie within a few miles of each other, and the sheltered waters of Sir Francis Drake Channel make for genuinely relaxed sailing between them. Tortola serves as the main hub, with Virgin Gorda, Jost van Dyke, and Anegada each offering different characters within a short crossing.
Particularly rewarding for families, first-time charterers, and those who want the Caribbean at a gentle pace.
Tortola
December to April
Virgin Gorda, Jost van Dyke
Sheltered, family-friendly
Destination 03
St Barts and St Martin
The French Caribbean.
St Barthelemy is small, fashionable, and remains one of the most exclusive destinations in the Caribbean. Gustavia’s harbour fills with yachts each winter, particularly around the New Year’s regatta that has become one of the great yachting events of the calendar. St Martin, twenty miles north, offers a busier base with the dual French and Dutch character of the island providing more variety.
The two islands together form the natural centre of the northern Caribbean charter route.
Gustavia
November to April
New Year’s Regatta
Antigua, Anguilla
Destination 04
The Grenadines
The quieter Caribbean.
The Grenadines are a scattered chain of small islands between St Vincent and Grenada, with a rhythm quieter than the northern Caribbean and some of the clearest water in the region. Mustique, Bequia, and the Tobago Cays each hold a distinct character, and the pace of a Grenadines charter tends to slow considerably compared to the Leewards.
The natural choice for guests who have already explored the busier parts of the Caribbean, or those seeking a quieter first experience of the region.
Mustique, Bequia
December to April
Tobago Cays
Quiet, undeveloped
Destination 05
The Bahamas
Seven hundred islands.
The Bahamas is a country of seven hundred islands, of which only thirty are inhabited. The Exumas hold some of the most photographed cruising in the world, from the swimming pigs at Big Major Cay to the sandbars of Compass Cay. Nassau and Paradise Island offer the country’s most developed hospitality, and Eleuthera’s pink beaches remain among the most beautiful in the region.
The Bahamas is close enough to the US mainland to make short charters practical, but expansive enough to reward longer voyages that extend into the more remote southern chain.
Nassau, Marsh Harbour
November to May
The Exumas
Direct from Florida
SECTION 03
Charter season
The Caribbean season runs from November through May, with the peak between December and April. Reliable trade winds, warm water, and consistent weather make this the most predictable cruising region in the world during the northern winter.
Hurricane season from June to October rules out cruising for most of the fleet, though the Bahamas remains viable through much of the year. New Year’s Week and the Antigua Yacht Show week are the busiest and most expensive of the calendar.
SECTION 04
Embarkation and logistics
The primary embarkation hubs are Antigua for Leewards charters, Tortola (BVI) for the Virgin Islands, St Martin for northern Caribbean itineraries, and Nassau or Marsh Harbour for the Bahamas. All are served by international flights or short connecting flights from Miami and San Juan.
Winter Caribbean charters often combine with land-based extensions in the region or with private jet transfers between islands for shorter charter windows.
November to May
Leewards, Windwards, Bahamas
Christmas, New Year
November, April, May
June to October
Seven to ten nights
SECTION 05
Sample seven-day itinerary
A directional guide to a BVI charter from Tortola. Every itinerary is shaped around the yacht, the guests, and the weather window.
Embarkation from Tortola in the afternoon, followed by a short crossing to Norman Island for the first anchorage.
Morning snorkelling at The Indians and The Caves, continuing east to Peter Island for lunch and swimming.
Passage to Cooper Island for the sheltered anchorage and dinner ashore at the beach club.
Continuing east to Virgin Gorda and The Baths, one of the most photographed sites in the Caribbean.
Full day at Anegada, the flat coral island with long beaches and famous lobster dinners at the beach shacks.
Return west to Jost van Dyke for a slower day at White Bay and dinner at Foxy’s or the Soggy Dollar.
Return to Tortola through the day. Disembarkation the following morning.
SECTION 06
Explore nearby
SECTION 07
Frequently Asked Questions
Which Caribbean region is best for first-time charterers?
The BVI is the most sheltered and easiest to navigate, with the shortest passages between islands. Antigua is also excellent as a starting point, with English Harbour as the historical centre of Caribbean yachting.
When is the best time to charter in the Caribbean?
December through April offers the most reliable weather and trade winds. November and May are excellent shoulder months with lower rates. Peak weeks like Christmas and New Year require booking six to twelve months in advance.
Are the Bahamas and Caribbean the same for chartering?
They are geographically close but distinct. The Bahamas is easier to reach from the US and offers shorter charter formats. The Caribbean proper is further south, with warmer year-round temperatures and the classic trade wind sailing.
Can I charter during hurricane season?
Most of the Caribbean fleet is either laid up or repositioned during hurricane season. The Bahamas remains partially viable and some operators continue but with insurance limitations. We advise on current conditions and options at the time of enquiry.
How do I combine multiple Caribbean destinations?
Longer charters of two weeks or more can move between the Virgin Islands, the Leewards, and the Grenadines. Private jet transfers between islands allow shorter charter windows to still cover multiple regions. We shape the routing around your dates and preferences.
PLAN A CHARTER
Every itinerary begins with a
conversation.
Tell us the destination that draws you, or ask us where might best
suit the trip you have in mind. We will shape something around it.