Four Seasons Yachts 2027 Caribbean Season Adds Costa Rica
Four Seasons Yachts has published its 2027 to 2028 Caribbean season, a set of 18 voyages that adds 18 destinations, and introduces Costa Rica as a new call, including Marina Papagayo and Bahía Golfito. For travelers, the practical change is more routing variety beyond the standard Eastern Caribbean loop, plus new itinerary timing opportunities in January and February that line up with humpback whale migration in Costa Rica's Pacific waters. The company is positioning the season as its second year in the region, following the debut of Four Seasons I, which the brand says will begin sailing in March 2026.
In its announcement, CEO Ben Trodd framed the new season as an expansion into "unexpected destinations," explicitly calling out Costa Rica as a way to deepen the Caribbean offering. That is marketing language, but the underlying traveler implication is real: Costa Rica is a different shore day than the typical small island rhythm, and it can change how travelers plan flights, pre nights, and post nights compared with a purely island hopping itinerary.
Four Seasons Yachts Caribbean Season: What Is New in 2027 to 2028
The headline addition is Costa Rica, with itineraries calling at Marina Papagayo and Bahía Golfito. Four Seasons is also leaning on overnight and late night stays, and it says select voyages will include a Panama Canal transit as part of broader Central America and Caribbean routing. If you are comparing yacht style products, that Panama Canal element is a meaningful differentiator because it tends to pull in a different buyer, one who wants a landmark passage alongside beach heavy ports.
Four Seasons also says it will rework holiday voyages for Thanksgiving, Christmas, and New Year in 2027, including Thanksgiving and Christmas routing through the Lesser Antilles, and a New Year trip that includes calls in Curaçao and Colombia. For repeat luxury cruisers, the operational significance is that holiday weeks are capacity constrained across the entire premium segment, so published holiday routing can matter as much as onboard product when advisors are trying to hold inventory early.
Who This Season Is Best For, and Where It Fits
This season is aimed at travelers who value long shore days, smaller ports, and unhurried time at anchor more than they value a dense port count. If you are the type of traveler who treats the ship as transportation between islands, you can get that elsewhere at a lower price point. If you want a yacht style cadence, meaning longer evenings in port, quieter anchor days, and the sense that the vessel itself is the destination, this is the segment Four Seasons is building toward.
Costa Rica is the clearest "fit signal" in the release. It appeals to a nature forward traveler who will actually use the shore program, and who is willing to treat the itinerary as an ecosystem and wildlife experience, not only a beach rotation. Four Seasons specifically ties some January and February sailings to humpback whale migration, and it highlights the likelihood of seeing dolphins, sea turtles, tropical birds, and monkeys. That makes timing matter more than usual: if wildlife is your priority, you would bias toward those months rather than choosing purely on holiday dates or port names.
For food and special interest travelers, remember that Four Seasons has already outlined a chef in residence concept for Four Seasons I. If culinary programming is part of the decision, it is worth tracking how those sailings map onto Caribbean weeks as the line publishes more details. (Four Seasons Yachts debuts chef-in-residence lineup)
How To Plan and Book Without Getting Boxed In
If you care about Costa Rica, plan your air strategy early, because it is not the same airlift and connection profile as the northeastern Caribbean. The lowest friction plan is usually an arrival buffer night, then a post voyage buffer night, because premium yacht itineraries are less forgiving when weather or port logistics compress the schedule. That is doubly true when an itinerary includes longer repositioning legs, or a Panama Canal transit, where timing changes can cascade into excursion windows and transfer timing.
If you are shopping the wider luxury yacht field, compare this season against other brands that are building winter Caribbean inventories for the same traveler. The risk in waiting is not only price, it is suite and itinerary availability on the exact week you want, especially for Thanksgiving, Christmas, and New Year. A good rule is to commit early when your trip is date locked, and stay flexible when your trip is experience locked. If you must travel during holiday weeks, book earlier than you think you need to, then adjust flights later as schedules firm up. (Ritz-Carlton Yacht Collection Caribbean 2026 to 2027)
For nature driven sailings, treat January and February as decision thresholds, not just "winter." Four Seasons is explicitly selling those weeks on whale migration, which implies they expect higher interest. If whales are the point, you are better off booking the right months first, then choosing between ports, and finally choosing between pre and post stays, rather than doing that in reverse.
Why Costa Rica Changes the Itinerary Math
Most Caribbean yacht seasons are optimized around short hops, predictable port operations, and easy tender days, which keeps the itinerary resilient when weather forces small adjustments. Adding Costa Rica shifts the mix toward a destination where the shore experience is more excursion intensive, and where guests may care more about protected areas, wildlife timing, and curated logistics than they do about a shopping heavy port afternoon. That changes what "a good day" looks like onboard, and it changes how guests value pre and post stays, because the land program can be as important as the sea days.
Four Seasons is also highlighting late night and overnight stays, which is not just romance copy. Operationally, those longer stays reduce the feeling of being rushed, and they make it easier to do waterfront dining, cultural programming, and early morning excursions without compressing everything into a single mid day window. In the same way, Panama Canal transits are not only a bucket list bullet. They often act as the "spine" of a longer itinerary, and that can pull travelers who want a narrative journey through Central America, not only a set of island snapshots.
Finally, the March 2026 start matters because it signals how close the product is to real world operation. Four Seasons' own fact sheet says Four Seasons I is scheduled to set sail on March 20, 2026. As that debut approaches, travelers should expect more granular details to land, including timing, shore experience specifics, and the practical booking rules that matter most to advisors, such as deposits, change terms, and how pre and post stays are packaged.