TrimTeam
The Caribbean
All destinations

The Caribbean

500+ yachts · december – april · Steady trade winds, turquoise anchorages and an island for every night.

Popular:

Har BarCatamaranWith or without a captain
Free from 15 Oct

FORT BURT MARINA6 GUESTS / 3 CABINS / 12.8 M
2026 · Lagoon 43

€7 528

week · captain included

€7 178 without a captain

Moorings 5000 Exclusive PlusCatamaranWith or without a captain
Free from 24 Jul 2027

WICKHAMS CAY II MARINA11 GUESTS / 4 CABINS / 15.4 M
2026 · Leopard 50

€11 222

week · captain included

€9 262 without a captain

Moorings 4600 - 4 Exclusive PlusCatamaranWith or without a captain
Free from 25 Nov

PALM CAY ONE MARINA10 GUESTS / 4 CABINS / 13.9 M
2026 · Leopard 46

€10 279

week · captain included

€8 249 without a captain

Moorings 4600 - 4 Exclusive PlusCatamaranWith or without a captain
Free from 21 Nov

WICKHAMS CAY II MARINA10 GUESTS / 4 CABINS / 13.9 M
2026 · Leopard 46

€6 859

week · captain included

€4 899 without a captain

Moorings 4600 - 4 Exclusive PlusCatamaranWith or without a captain
Free from 3 Oct

MARINA FORT LOUIS10 GUESTS / 4 CABINS / 13.9 M
2026 · Leopard 46

€7 047

week · captain included

€5 227 without a captain

Moorings 4600 - 4 Exclusive PlusCatamaranWith or without a captain
Available this week

PLACENCIA10 GUESTS / 4 CABINS / 13.9 M
2026 · Leopard 46

€6 869

week · captain included

€5 749 without a captain

The Caribbean is winter sailing at its best — warm trade winds, short crossings between islands, white-sand bays and a rum punch at anchor. From the British Virgin Islands to the Grenadines, our crewed catamarans turn island-hopping into the easiest luxury there is.

Anchorages we love

01

British Virgin Islands

The world’s easiest cruising ground — line-of-sight hops, protected anchorages, the Baths at Virgin Gorda and the bar at Jost Van Dyke.

02

The Grenadines

Tobago Cays inside the reef, turtles in the shallows, and barefoot beach bars from Bequia to Mustique.

03

St Martin & St Barths

French-Caribbean style — Gustavia harbour, long lunches, and a quick reach between two of the chicest islands in the sea.