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Caribbean · Charter Guide
Caribbean
The yacht charter guide — when to sail, where to anchor, and the vessels that run it best.
The brief
When the Mediterranean season ends, the fleet crosses the Atlantic to the Caribbean — the winter mirror, and arguably the easiest, most rewarding sailing on Earth. Steady trade winds, short hops between islands, and anchorages that need no introduction: the British Virgin Islands for first-timers and families, chic Saint-Barthélemy over the New Year, the wild Grenadines and the pale flats of the Bahamas. A Caribbean charter trades the social intensity of the Med for turquoise simplicity — a beach bar reached only by tender, a reef off the swim platform, and a rum punch as the trades drop at dusk.
When to sail
Best time to visit
Peak season
December – April
Shoulder
November & May
Best months
Dec · Jan · Feb · Mar · Apr
The Caribbean charter season is the dry, breezy winter — December through April — the mirror of the Mediterranean summer. The Christmas and New Year weeks are the social peak (and book a year ahead); January to April offers the steadiest trade winds and the finest sailing. The hurricane season (roughly June–November) is avoided.
The route
Signature anchorages
01
The British Virgin Islands
Excellent shelterThe world’s most forgiving charter ground — line-of-sight hops in flat, protected water. The Baths at Virgin Gorda, the bars of Jost Van Dyke, and Norman Island’s caves make a perfect first week.
18.4300°N, 64.6200°WMooring fieldsBeach barsSnorkellingProvisioning
02
Saint-Barthélemy
Fair shelterThe Caribbean’s most stylish island — anchor off Gustavia or Colombier, with the boutiques, beach clubs and a New Year’s Eve in the roads that draws the world’s fleet.
17.9000°N, 62.8300°WGustavia harbourBeach clubsFine diningBoutiques
03
The Grenadines
Good shelterThe wilder, quieter south — the Tobago Cays marine park, where you anchor behind a horseshoe reef among turtles, and the laid-back islands of Mustique, Bequia and Mayreau.
12.6300°N, 61.3500°WMarine parkReef snorkellingIsland villagesBeach BBQ
04
The Exumas, Bahamas
Good shelterNot strictly the Caribbean but a popular winter extension — 365 cays of impossibly pale water, swimming pigs at Big Major, and the sandbars of the Exuma Land and Sea Park.
24.1800°N, 76.4400°WSandbarsSnorkellingMarine parkBeach landings
At the table
What you'll eat
The Caribbean table is a Creole crossroads — African, French, Indian and indigenous flavours layered over the catch of the reef and the rum of the islands. Aboard, expect grilled mahi-mahi and lobster, jerk spice, tropical fruit and a cellar of the region’s finest rums.
Caribbean Spiny Lobster
Grilled over coals and split with garlic butter — at its best in the Grenadines and the BVI, often bought from a passing fisherman.
Jerk-Spiced Fish
Reef fish or chicken in the fiery allspice-and-scotch-bonnet marinade of the islands.
Conch Fritters
A Bahamian and Caribbean staple — the sea snail, battered and fried, served with a lime-spiked dip.
Rum & Ti’ Punch
The French islands’ ti’ punch — rhum agricole, lime and cane syrup — and the aged sipping rums of the wider Caribbean.
Ashore
Cultural highlights
The Baths, Virgin Gorda
Surreal granite boulders forming grottoes and tidal pools on the beach — one of the Caribbean’s natural set-pieces, reached by tender.
Foxy’s, Jost Van Dyke
The legendary beach bar and its Old Year’s Night party — a Caribbean institution as much as a watering hole.
Tobago Cays Marine Park
Anchor behind Horseshoe Reef to swim with green turtles in a protected lagoon — a highlight of any Grenadines voyage.
Gustavia, St Barths
A pocket-sized harbour town of red roofs and rue Lafayette boutiques, French to its core and the social centre of the winter season.
Good to know
Caribbean charter — questions answered
When is the best time for a Caribbean charter?
December to April — the dry, breezy winter and the mirror of the Mediterranean summer. The Christmas and New Year weeks are the social peak and book a year ahead; January to April offers the steadiest trade winds.
Where do Caribbean charters cruise?
From the easy, sheltered British Virgin Islands to chic Saint-Barthélemy, the wild Grenadines and the pale flats of the Bahamas — itineraries are tailored to your pace and party.
Is the Caribbean good for first-time charterers?
The British Virgin Islands in particular offer short, line-of-sight hops between sheltered anchorages with steady trade winds — among the most relaxed and forgiving cruising anywhere.
Do you avoid hurricane season?
Yes. The Caribbean charter season runs December to April; the hurricane season of roughly June to November is avoided.
Cruising ground
Plan a Caribbean voyage — vessels, seasons & map