There’s a different way to see the Caribbean when your front door opens onto a marina instead of a mega-port. That’s one of the major premises behind the rising trend of ultra-luxe, small-ship cruising — including the soon-to-debut Four Seasons Yachts, which makes its first voyage in the region next month.
And it’s already set for 2027.
In 2027, Four Seasons Yachts is leaning further into that idea, unveiling a new Caribbean season built around 18 curated voyages and 18 additional destinations — including a first-time expansion into Costa Rica.
The newly announced 2027–2028 season marks the brand’s second year sailing the Caribbean, following its Mediterranean debut in March 2026 and its inaugural Caribbean winter season later this year. The focus remains consistent: smaller harbors, intimate marinas, and itineraries that put you directly into the character of each port.
“Each new season represents an avenue to further refine and elevate the Four Seasons Yachts experience,” said Ben Trodd, CEO of Marc-Henry Cruise Holdings Ltd., joint owner and operator of Four Seasons Yachts, in a statement announcing the new lineup.
Here’s what travelers can expect from the expanded Caribbean program.
Costa Rica Joins the Itinerary for the First Time
The headline addition is Costa Rica, a destination long favored by private yachters but rarely integrated into luxury cruise itineraries in this way.
Four Seasons Yachts will call on Marina Papagayo and Bahía Golfito, gateways that place you within reach of rainforest-lined coastlines, protected wildlife refuges, and stretches of Pacific shoreline known for their biodiversity. January and February sailings are timed to align with the seasonal migration of humpback whales into Costa Rica’s Pacific waters, giving guests the chance to spot the mammals offshore alongside dolphins and sea turtles.
Shore and Sea Experiences in Costa Rica are designed to go beyond a brief port stop, encouraging deeper exploration of the country’s ecosystems and culture. Travelers can also extend their time with pre- and post-voyage stays at luxury accommodations on land, pairing a yacht journey with time at Four Seasons’ properties in the country.
It’s a notable expansion that shifts the Caribbean conversation slightly westward, connecting Central America and the islands into a broader sailing canvas.
Cartagena to St Barths: A Wider Caribbean Sweep
Beyond Costa Rica, the 2027–2028 season charts a diverse route map across the region. Voyages will include calls in Cartagena, where colonial architecture lines the waterfront, and Gustavia in St Barths, known for its yacht-filled harbor and boutique-lined streets.
The structure of each sailing balances time ashore with extended hours at anchor. During designated Marina Days, the yacht’s floating platform becomes a launch point for swimming, paddleboarding, and other water sports directly off the vessel. The emphasis is on unhurried access to the sea, rather than quick-turn port visits.
Several itineraries feature overnight and late-night stays, giving you time to linger for waterfront dinners, evening walks through historic harbor towns, or a quiet return tender ride under Caribbean skies. Select voyages will also include a Panama Canal transit, pairing a bucket-list engineering passage with broader journeys through Central America and the Caribbean basin.
For travelers beginning or ending in Colombia, curated pre- and post-stays in Cartagena will extend the experience on land, blending the yacht’s design-forward aesthetic with the city’s walled streets and Caribbean coastline.
A Festive Season Designed for the Caribbean
The line is also reimagining the holidays at sea in 2027, with dedicated Thanksgiving, Christmas, and New Year voyages.
Thanksgiving and Christmas sailings will focus on the Lesser Antilles, with itineraries weaving through islands including Saint Lucia, Martinique, Antigua, and Nevis. Expect a mix of beach time, late evenings ashore, and celebratory gatherings on board.
The New Year voyage expands the geographic footprint, with calls in Curaçao and Colombia to mark the turn of the calendar. The pairing brings together colorful Dutch Caribbean streetscapes and Colombia’s coastal energy for a different kind of year-end celebration.
Rather than concentrating activity into a single night, these voyages spread the experience across multiple destinations, combining festive programming with the rhythm of a Caribbean sailing.
Second Caribbean Season Builds on 2026 Debut
Four Seasons I will make its inaugural voyage in March 2026, beginning in the Mediterranean before repositioning to the Caribbean for its first winter season later that year. The newly announced 2027–2028 lineup represents the brand’s second Caribbean cycle, expanding both the geographic reach and the number of sailings in the region.
The approach remains rooted in smaller ports and curated experiences rather than traditional cruise circuits. By focusing on marinas such as Marina Papagayo and ports like Gustavia, the yacht is positioned to dock where larger ships cannot, allowing guests to step directly into town centers or coastal enclaves.
With 18 voyages and 18 new destinations added to the map, the 2027 Caribbean season signals a broader ambition: to connect well-known island capitals with less-traveled coastal gateways across the Caribbean and Central America — all from the vantage point of a Four Seasons–designed yacht.
Caitlin Sullivan
2026-02-27 16:30:00