Four Seasons Yachts Wants to Take You to the Caribbean for the Holidays

What’s Four Seasons’s version of spreading holiday cheer? Sailing around the Caribbean on a luxury superyacht, of course. 

Four Seasons Yachts just revealed nine new voyages to the Bahamas and the Caribbean to celebrate the 2026-2027 holiday season. The portfolio expansion includes itineraries aboard its Four Seasons I ship which will set sail between November 19, 2026, and January 31, 2027. Meaning, you can escape the chill and celebrate Thanksgiving, Christmas, and even ring in the New Year at sea.  

“Building from the excitement and interest of our initial Mediterranean and Caribbean journeys, we are thrilled to unveil the final set of exceptional voyages for Four Seasons Yachts inaugural year,” says Alejandro Reynal, president and CEO of Four Seasons, in a press statement.

Four Seasons I will embark on a 10-night Thanksgiving journey from St. John’s, Antigua, roughly one week before U.S. travelers would normally be slicing into their turkeys. Instead, you’ll be treated to a Caribbean-inspired feast prepared by the Four Seasons culinary teams with the picturesque Saint Pierre, Martinique as the backdrop. In addition, the trip includes stops at Soper’s Hole in the British Virgin Islands and Prickly Bay in Grenada where seafarers can hang out at laid-back beach bar or check out a world-famous underwater sculpture park. 

Four Seasons Yachts will offer sailings around the Caribbean for the 2026-2027 holiday season. Four Seasons

All will be merry and bright if you opt for the seven-night Christmas adventure. Guests will kick off the excursion with a stay at the sunny Four Seasons Hotel at the Surf Club in South Florida. Then, it’s off to Great Harbour on Jost Van Dyke for Painkiller cocktails, which originated at the island’s iconic Soggy Dollar Bar. By the Christmas Eve, the vessel arrives in St. Barths where you’ll trade animated displays for twinkling harbor lights, before zooming to Palmetto Point on the island of Barbuda for the big day. Here, travelers can dig into a beachside banquet and bask in local holiday traditions. The journey wraps on the powder-soft shores of Sint Maarten at Four Seasons Resort and Residences Anguilla. 

Meanwhile, the countdown to 2027 will take place on a seven-night charter in the middle of the Atlantic with a lavish New Year’s Eve party that includes flowing champagne and a relaxing beach day in the Exuma Sound to start the year. Of course, for those looking to spend their entire Twixmas break on the open ocean, there’s an epic 14-night sailing that combines both trips. 

Authors

Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, entertainment, dining, travel to…

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