Four Seasons Yachts Expands Caribbean Season with 18 New Sailings, Adds Costa Rica for 2027–2028

Image: Four Seasons Yachts 2027-2028 Caribbean Season (Photo Credit: Four Seasons Yachts)
Image: Four Seasons Yachts 2027-2028 Caribbean Season (Photo Credit: Four Seasons Yachts)
TravelPulse Staff
by TravelPulse Staff
Last updated: 8:40 AM ET, Wed February 25, 2026

Four Seasons Yachts has released details of its 2027–2028 Caribbean season, outlining 18 voyages and 18 new destinations across the region.

The upcoming season will mark the company’s second year sailing in the Caribbean. The brand will debut in the Mediterranean in March 2026, followed by its first Caribbean winter season later that year.

“Each new season represents an avenue to further refine and elevate the Four Seasons Yachts experience--expanding into exceptional, unexpected destinations while artfully curating journeys around the individual passions of our guests,” says Ben Trodd, CEO, Marc-Henry Cruise Holdings Ltd., Joint Owner/Operator of Four Seasons Yachts.

RELATED: Four Seasons Yachts Reveals 2027 Mediterranean Season

“The Caribbean has long been a yachter's sanctuary, and the introduction of destinations such as Costa Rica enables us to deepen our distinctive offering while unveiling new and compelling opportunities for discovery.”

Costa Rica added to the lineup

For the first time, voyages will call in Costa Rica, including stops at Marina Papagayo and Bahía Golfito. Sailings in January and February are timed to coincide with the seasonal migration of humpback whales to the country’s Pacific waters. Guests may also encounter dolphins, sea turtles and tropical wildlife during shore excursions.

The company says pre- and post-voyage stays in Costa Rica will allow travellers to extend their time on land, with additional shore experiences offered throughout the country.

Caribbean highlights and Panama Canal crossings

Beyond Costa Rica, the season includes ports such as Cartagena and Gustavia in St. Barths. Itineraries are designed to balance time ashore with days at anchor, when guests can access water sports directly from the vessel during dedicated marina days.

RELATED: Inside the Four Seasons Explorer, Palau’s Floating Luxury Resort

Several voyages will feature overnight or late-night stays in port. Select itineraries will also include a transit through the Panama Canal as part of broader Central America and Caribbean routes.

Pre- and post-stays in Cartagena will also be available.

Holiday sailings planned

The 2027 festive season will include dedicated Thanksgiving, Christmas and New Year voyages.

Thanksgiving and Christmas itineraries will sail through the Lesser Antilles, including Saint Lucia, Martinique, Antigua and Nevis. The New Year voyage will call in Curaçao and Colombia.

The first vessel in the fleet, Four Seasons I, is scheduled to make its inaugural voyage in March 2026. A second vessel, Four Seasons II, is expected to debut in 2027.

Four Seasons Yachts is a joint venture between Marc-Henry Cruise Holdings Ltd. and Italian shipbuilder Fincantieri, in partnership with Four Seasons.

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