Four Seasons Yachts has unveiled its 2027–2028 Caribbean season, featuring 18 curated voyages and 18 new destinations, including the marquee addition of Costa Rica. From whale-watching along the Pacific coast to late-night stays in Cartagena and festive sailings through the Lesser Antilles, each itinerary is designed around intimate marinas and lightly visited ports. This is luxury travel at sea, built around discovery, depth, and genuine connection to place.
The Caribbean has always rewarded those who arrive by sea. There's a particular kind of access that comes with dropping anchor in a harbour too shallow for large ships, or pulling into a private marina where the jungle meets the waterline.
Four Seasons Yachts has built its entire philosophy around exactly this kind of travel, and its newly announced 2027–2028 Caribbean season reflects that ambition at full scale. The brand has unveiled 18 curated voyages and 18 new destinations, headlined by Costa Rica's debut as a marquee yachting destination.
This will mark the brand's second year operating in the Caribbean, following its Mediterranean debut in March 2026 and its inaugural Caribbean winter season later that year. With Four Seasons II set to debut in 2027, the fleet is growing quickly, and this latest announcement makes clear that the vision extends well beyond standard luxury cruising.
Costa Rica: a new frontier for luxury sea travel
Of all the additions in the 2027–2028 season, Costa Rica stands out as the boldest choice. The country's Pacific coastline is among the most biodiverse on the planet, and it has historically been difficult to experience meaningfully without spending days travelling overland. Arriving by yacht changes that entirely.
Key ports of call in Costa Rica
Voyages calling on Costa Rica will dock at two exclusive gateways, each offering direct access to ecosystems and coastlines that larger ships simply cannot reach:
| Marina | Location | Highlights |
|---|---|---|
| Marina Papagayo | Guanacaste, Pacific Coast | Wildlife refuges, snorkelling, and tropical forest access |
| Bahía Golfito | Southern Pacific Zone | Protected ecosystems, remote beaches, and biodiversity hotspots |
Wildlife and natural experiences
Sailings scheduled for January and February are timed to coincide with the seasonal migration of humpback whales along the Pacific coast. Beyond the whales, guests can expect encounters with:
- Dolphins and sea turtles in coastal waters
- Tropical birds and howler monkeys along jungle shorelines
- Diverse marine life across protected reef zones
Extending the experience on land
Pre- and post-voyage stays in Costa Rica are available through Four Seasons' network of properties. Multiple Shore and Sea Experiences allow guests to venture into the country's volcanoes, cloud forests, and coastal reserves, well beyond the reach of a single port call.
The Caribbean, designed for discovery
The 2027–2028 season spans a carefully curated collection of destinations that reflect the region's remarkable diversity, from sun-bleached colonial architecture to turquoise anchorages accessible only by smaller vessels.
Standout destinations at a glance
| Destination | Country | Why it's worth it |
|---|---|---|
| Cartagena | Colombia | Colourful walled Old Town, vibrant waterfront, rich cultural history |
| Gustavia | St Barths | Refined harbour, world-class dining, boutique atmosphere |
| Panama Canal | Panama | Bucket-list engineering marvel, Central American gateway |
Pre- and post-voyage land stays in Cartagena allow guests to explore the city's history, cuisine, and nightlife well beyond the typical port call.
How days at sea unfold
Each voyage is built around a rhythm that balances active exploration with genuine rest. Highlights of the onboard experience include:
- Marina Days: swimming, water sports, and lounging directly from the vessel
- Overnight and late-night stays: time ashore after dark, when harbour towns reveal a different character
- Early-morning departures: glassy seas and quiet ports before the day begins
- Tender launches: direct access to beaches and coves unreachable by larger ships
Festive season at sea
One of the most distinctive aspects of the 2027–2028 calendar is its suite of dedicated holiday voyages. Spending Thanksgiving or Christmas on a yacht in the Caribbean may not be a traditional choice, but Four Seasons Yachts makes a compelling case for why it should be.
Holiday voyage breakdown
| Voyage | Season | Key Destinations |
|---|---|---|
| Thanksgiving sailing | November 2027 | Lesser Antilles (Saint Lucia, Martinique, Antigua, Nevis) |
| Christmas sailing | December 2027 | Lesser Antilles (Saint Lucia, Martinique, Antigua, Nevis) |
| New Year voyage | December 2027/January 2028 | Curaçao, Colombia |
The Lesser Antilles islands in focus
The Thanksgiving and Christmas sailings thread through four distinct island personalities:
- Saint Lucia: dramatic volcanic peaks, lush rainforest trails, and secluded beaches
- Martinique: French Caribbean culture, exceptional cuisine, and renowned rum distilleries
- Antigua: 365 beaches, a UNESCO-listed historic English Harbour, and excellent sailing conditions
- Nevis: a quieter gem with plantation-era atmosphere and natural thermal springs
The New Year voyage broadens the horizon, with calls in Curaçao and Colombia. Both destinations bring cosmopolitan energy and cultural richness, making them a fitting way to close one year and begin the next.
About Four Seasons I and the vessel experience
Four Seasons I is a collaboration between Marc-Henry Cruise Holdings Ltd., Italian shipbuilder Fincantieri, and Four Seasons' hospitality team. The design is residential in character, prioritizing space and comfort over the density of a conventional cruise ship.
Vessel highlights at a glance
| Feature | Detail |
|---|---|
| Suite style | All-suite, residential-style accommodations |
| Funnel Suite glass | 9,975 sq ft (927 sq m) — largest contiguous piece of glass at sea |
| Onboard marina | Transverse design, opens port to starboard for direct water access |
| Fleet expansion | Four Seasons II debuts in 2027 |
As Ben Trodd, CEO of Marc-Henry Cruise Holdings Ltd., explains: "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."
Where the sea takes you next
The 2027–2028 Caribbean season represents a genuine evolution in luxury sea travel. By pairing intimate access to lightly visited ports with the full weight of Four Seasons hospitality, and by introducing a destination as biologically rich as Costa Rica, the programme charts a course few competitors can follow.
The Panama Canal transits, festive holiday sailings, and seamless land-and-sea extensions in Cartagena and Costa Rica all point to an itinerary calendar built with real intention. These are voyages shaped by curiosity and a genuine respect for the places being visited.
For travellers who have always wanted to experience the Caribbean from the waterline rather than the shoreline, and who refuse to compromise on comfort or depth of experience, the timing has never been better. Four Seasons I sets sail on its inaugural voyage in March 2026, with the full 2027–2028 Caribbean season open for booking.
To connect with a Personal Yacht Consultant, call 1-800-705-7580 or visit fourseasons.com to inquire about a voyage and sign up for exclusive updates.
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