Winter sunshine from the chic Leewards to the lush Windwards — beach bars, trade winds and turquoise anchorages.
Request your dossierShort hops, sandy anchorages and laid-back island life make the Caribbean the quintessential winter escape.
The Leewards bring chic harbours and events, while the Windwards reward with lush scenery and kite-friendly bays.
Warm water, predictable trades and a relaxed shoreside scene are perfect for water toys and beach days.
Anchorages & islands that define a Caribbean winter.
Glamour, dining and festive-season buzz.
365 beaches and English Harbour history.
Palm-lined Tobago Cays and smooth trades.
Some open-water legs can be lively; stabilisers, good route timing and wind-sports toys keep things fun and comfortable.
Customs and immigration between islands are straightforward with an experienced crew; your captain coordinates formalities en route.
Leeward itineraries lean chic marinas and nightlife, while the Windwards reward with nature-forward anchorages and slightly longer legs.
7–10 days for the Leewards; 10–14 days for the Windwards including the Grenadines — plenty of time to enjoy anchorages.
Yes. Choose routes with shorter open-water sections and plan morning passages for calmer seas.
Prime season is winter. We monitor systems closely and recommend appropriate cover and routing.
Often yes, subject to local rules and protected areas. We arrange permits and full logistics.
Seabobs, SUPs, foils and kites (spot-dependent). Tell us your wishlist and we will match yacht & gear to your activity level.
Kevin Benning
Founder & Retail Broker
“I am always available as your personal point of contact to ensure a seamless experience.”