Highlights
Anchorages & islands on a classic Caribbean route.
Winter sunshine from the chic Leewards to the lush Windwards – beach bars, steady trade winds and turquoise anchorages.
Request curated yachtsShort hops, sandy bays and laid-back island life make the Caribbean the ideal winter escape.
The Leewards deliver chic harbors, boutiques and events; the Windwards shine with lush nature, sailing breezes and kite spots.
Warm water, reliable trades and easygoing beach culture create perfect conditions for water toys and long beach days.
Anchorages & islands on a classic Caribbean route.
Open water can feel lively on some legs. Stabilisers, smart routing and wind-sports toys keep it fun and comfortable.
Customs and immigration between islands are handled seamlessly by the crew; with an experienced captain the flow stays relaxed.
The Leewards offer chic marinas and nightlife; the Windwards reward with nature, snorkel sites and a few longer passages.
7–10 days for the Leewards; 10–14 days for the Windwards including the Grenadines – ideal for unhurried anchor time.
Yes. Choose routes with shorter open passages and schedule any longer legs in the morning when seas are calmer.
Prime season is winter. We monitor weather continuously and recommend suitable insurance and flexible routing alternatives.
In many areas yes – subject to local rules and protected zones. We obtain permits and handle logistics and equipment.
Seabobs, SUPs, foils and kites (spot-dependent). Share your wishlist – we’ll 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.”
