Crewed luxury charter
Yacht Charter Caribbean
Leewards, Windwards & the Virgins
When the Mediterranean cools, the Caribbean season opens. Short, warm passages between islands, dependable trade winds and postcard anchorages — a crewed yacht turns a string of islands into one seamless, sun-soaked week.
The Caribbean is the winter half of the charter year, and it is tailor-made for a crewed yacht. The islands sit close together, the north-east trade winds are steady and reliable, and the water is a warm, luminous blue — so a week becomes an easy chain of short hops, each ending in a palm-fringed anchorage with a beach bar at one end and empty sand at the other.
The British Virgin Islands are the classic starting point: a tight, sheltered cluster of islands where the sailing is forgiving and the anchorages are legendary — the Baths on Virgin Gorda, the sandbars off Anegada, painkillers at Jost Van Dyke. Further options run from chic St Barths, glamorous at New Year, down to the quiet, unspoilt Grenadines and the Tobago Cays. It is the definitive escape from a northern winter.
November to May — the dry, breezy winter season, opposite to the Mediterranean.
Where a crewed charter takes you in Caribbean
British Virgin Islands
Tight cluster of islands and calm water — the classic first charter.
St Barths
Chic harbours, fine dining and glamorous New Year anchorages.
The Grenadines
Tobago Cays and quiet, unspoilt sailing further south.
Seven days in Caribbean
One way to spend a week — your captain tailors the exact route to the weather, your pace and what you want to see. It is a starting point, not a fixed schedule.
- Day 1Tortola
Board in the BVI's hub and cruise to Norman Island for a first snorkel.
- Day 2The Baths, Virgin Gorda
Giant granite boulders and grottos — the Caribbean's most famous swim.
- Day 3Anegada
A flat coral island of empty beaches and fresh lobster ashore.
- Day 4Jost Van Dyke
White Bay's beach bars and the bubbling natural pools.
- Day 5Cooper / Salt Island
Quiet anchorages and the wreck of the RMS Rhone to dive.
- Day 6Peter Island
A last empty bay and a sundowner at anchor.
- Day 7Return
Back to Tortola, or extend toward St Barths and the leeward islands.
See more sample routes in our one-week charter itinerary guide.
Yacht charter in Caribbean — your questions
When is the Caribbean yacht charter season?
November to May — the dry, breezy winter season, the natural counterpart to the Mediterranean summer.
Where do yacht charters go in the Caribbean?
The British Virgin Islands for calm, easy island-hopping; St Barths for chic harbours and fine dining; and the Grenadines for quieter, unspoilt sailing further south.
Why charter a yacht in the Caribbean?
Short warm passages, dependable trade winds and postcard anchorages turn a string of islands into one seamless, sun-soaked week — ideal winter sun when the Mediterranean cools.
More in the charter guides and FAQ.
Crewed charters in Caribbean
Match me →Caribbean is a destination our brokers arrange on request. We don't list a fixed fleet here — instead we source the right crewed yacht for your dates from our partner network, so you always get a current, honestly-priced option.
Plan a Caribbean charter →Rates are indicative and confirmed by your broker on enquiry.
Sail on to…
If Caribbean appeals, these cruising grounds share its rhythm — pair them across a season, or ask us which suits your dates best.
