There’s a different way to see the Caribbean when your front door opens onto a marina instead of a mega port. This is one of the key premises behind the rising trend of ultra-luxury small ship cruises, including the soon-to-debut Four Seasons Yachts, which will set sail in the region next month.
And it has already been set for 2027.
In 2027 Four Seasons Yacht is further focusing on this idea, unveiling a new Caribbean season built around 18 curated sailings and 18 additional destinations. 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 first Caribbean winter season later this year. Focus remains consistent. This itinerary takes you through small ports, intimate marinas, and the unique characteristics of each port.
“Each new season represents a way to further improve and enhance the Four Seasons Yachts experience,” Ben Trodd, CEO of Marc-Henry Cruise Holdings Ltd., co-owner and operator of Four Seasons Yachts, said in a statement announcing the new lineup.
Here’s what travelers can expect from our expanded Caribbean program.
Costa Rica joins the itinerary for the first time.
Adding to the headlines is Costa Rica, a country that has long been a favorite of private yacht travelers but is rarely incorporated into luxury cruise itineraries in this way.
Four Seasons Yachts Requests Marina Papagayo and Golfito BayIt is the gateway to the Pacific coastline, famous for its rainforest-lined coastline, wildlife reserves and biodiversity. January and February sailings are timed to coincide with humpback whale migration season in Costa Rica’s Pacific waters, giving guests the opportunity to spot mammals offshore along with dolphins and sea turtles.
Costa Rica’s coastal and ocean experiences are designed to encourage deeper exploration of Costa Rica’s ecosystem and culture beyond a simple port stop. Travelers can also extend their time by staying in luxury accommodations on land before and after their voyage, or they can also spend time at a Four Seasons hotel onshore along with their yacht trip.
It’s a notable expansion that moves the Caribbean conversation slightly west, linking Central America and the islands into a broader sailing canvas.
From Cartagena to St. Barths: A Wider Caribbean Sweep
Beyond Costa Rica, the 2027-2028 season features a variety of route maps throughout the region. Voyages include the following currencies: CartagenaA place where colonial-style buildings line the coast, Gustavia of St. Barthis famous for its yacht-filled port and boutique-lined streets.
The structure of each voyage balances time on shore with time at anchor. During designated Marina Days, the yacht’s floating platform serves as a launching pad for swimming, paddleboarding and other water sports directly from the vessel. The focus is on unhurried access to the sea rather than hasty port visits.
Several itineraries include overnight and late-night stays, allowing you to enjoy dinner on the waterfront, an evening stroll along the historic port town, or a quiet round-trip ride under the Caribbean sky. Some voyages also include: Passing through the Panama CanalIt combines bucket list engineering courses with wider travel through Central America and the Caribbean Basin.
For travelers starting or ending in Colombia, pre- and post-accommodation in Cartagena extends the experience on land, blending the yacht’s design-oriented aesthetic with the city’s walled streets and Caribbean coastline.
A festive season designed for the Caribbean
The line is also reinventing vacations at sea for 2027. Thanksgiving, Christmas, New Year sailing.
Thanksgiving and Christmas sailings will be the focus next. Lesser AntillesItinerary through the island, including: Saint Lucia, Martinique, Antigua, Nevis. It’s a mix of beach time, late evenings on the beach, and celebratory gatherings on board.
New Year’s Voyage expands your geographical space through the phone. Curaçao and Colombia To mark the turn of the calendar. This combination combines the colorful Dutch Caribbean street scene with the coastal energy of Colombia for a holiday celebration with a difference.
Rather than concentrating the activities over one night, these sailings spread the experience across multiple destinations, combining a festive program with the rhythms of a Caribbean sailing.
A second Caribbean season is scheduled to debut in 2026.
Four Seasons I will set sail in March 2026, starting in the Mediterranean before moving back to the Caribbean for her first winter season later that year. The newly announced 2027-2028 lineup represents the brand’s second Caribbean cycle, expanding both its geographic reach and the number of sailings in the region.
This approach is rooted in smaller ports and curated experiences rather than the traditional cruise circuit. Focusing on marinas such as Marina Papagayo and ports such as Gustavia, yachts are positioned where larger ships cannot dock, allowing guests direct access to the city center or coastal areas.
With 18 sailings and 18 new destinations added to the map, the 2027 Caribbean season represents broader ambitions. That means traversing the Caribbean and Central America, linking well-known island capitals and less-traveled coastal gateways from the vantage point of a Four Seasons-designed yacht.
