The 2027-2028 Caribbean season unfolds across 18 newly curated voyages revealed through the spirit of yachting. Introducing 18 destinations accessible only to smaller vessels and private yachts, these voyages move from Cartagena’s colourful streets and Costa Rica’s biodiverse Pacific coast to a rare, full-day passage through the Panama Canal. Each journey invites unhurried exploration, with select sailings timed for the holiday season.
Experience the world-renowned service of Four Seasons, where every need is anticipated, and every moment feels effortless.
Prioritising depth over distance, this collection foregoes traditional routes in favour of intimate marinas and untouched shorelines. Later stays and overnights invite greater immersion and the opportunity to spend more time ashore at Four Seasons properties. Timed for the season, these voyages sail in temperate conditions ideal for exploration, with select departures aligned with peak wildlife migrations.

Sail along Costa Rica’s Pacific coast, where lush rainforests meet crystalline seas rich with wildlife. Seven- to twelve-night journeys explore secluded harbours and tranquil coastal inlets, revealing emerald canopies alive with exotic birds and monkeys, and open waters where humpback whales breach during their northerly migration. Raw natural beauty ashore pairs seamlessly with effortless relaxation aboard, with the option to extend your stay at the Four Seasons Resort Costa Rica.

Mark the holiday season aboard Four Seasons I as you navigate warm Caribbean waters toward sun-kissed isles. These special sailings call on beloved yachting havens of the Lesser Antilles, including St Lucia, Antigua, and Nevis. Select voyages venture farther afield to Curaçao, Colombia, and beyond. From celebratory gatherings aboard to idyllic afternoons on the water and late stays in iconic destinations, our holiday voyages offer an unforgettable alternative to traditional festivities.

Trace a path from the shores of Papagayo along Central America’s Pacific coast before entering the Panama Canal for a full-day experience of one of the world’s most remarkable feats of engineering. As you travel from the tranquil expanse of Gatun Lake to the shifting jewel tones of the Caribbean Sea, crossing the Canal aboard Four Seasons I becomes a defining highlight of the voyage, experienced in effortless comfort.