12-17 February 2027

Where to charter for Presidents' Day

The February long weekend, and the only one that falls in the middle of the Caribbean high season. Boats are tight and booked early.

Travel window 12-17 February 2027

Start looking before this date 19 Dec 2026

Typical trip 4 days

The date above is the travel window minus 55 days. Our own enquiries put the median gap between first contact and departure at 40 days, so this has you looking early rather than late.

Where to go for a 4-day yacht charter

Charter grounds whose season suits these dates. Ordered by how well the window fits, not by how many yachts we hold there.

Why these charter grounds suit the dates

Bahamas

Winter is prime time – the Exumas' sandbars and swimming pigs in settled trade-wind weather. Hurricane season (June–November) sits outside the charter calendar.

British Virgin Islands

Steady 15–20 knot trade winds and line-of-sight island hops make the BVI the world's most forgiving blue-water playground.

St Barths

The Caribbean's most glamorous harbour – New Year's Eve in Gustavia is the yachting world's winter rendezvous, booked many months ahead.

USVI

St Thomas, St John and St Croix pair US convenience with BVI-grade sailing – half of St John is national park, its bays on permanent protection.

Turks and Caicos

Grace Bay's impossible turquoise and mile after mile of uninhabited cays – shallow-draft heaven on the edge of the third-largest reef system on earth.

Anguilla

Powder-white sands and glassy leeward anchorages – Anguilla pairs Caribbean trade-wind sailing with some of the region's finest beach dining.

Events during these dates

Already happening while you are away, and worth building the route around.

Miami International Boat Show 10 – 14 February 2027 USA

Not sure which of these suits you?

Tell us who is travelling and roughly when, and a broker will come back with the two or three that actually fit.

Talk to a broker