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August 27, 2025
The Ritz-Carlton Yacht Collection is sharing its lineup of Winter 2026-2027 Caribbean season sailings aboard the luxury-at-sea yacht, Ilma.
From November 2026 through April 2027, the yacht will sail more than 20 crafted itineraries from three to seven nights. An expanded selection of shorter three-and-four-night escapes enables travelers to experience the Caribbean in spacious suite accommodations with world-class cuisine and personalized service. Measuring 790 feet (241 meters), Ilma accommodates up to 448 guests in 224 suites, each with a private terrace offering uninterrupted sea views.
For the first time, Miami will join San Juan as a new embarkation point with numerous flight options and the port just 15 minutes from Miami International Airport.
“The winter season is a meaningful time for travel, when many of our guests are looking to celebrate the holidays or escape to warmer shores,” said Ernesto Fara, President of The Ritz-Carlton Yacht Collection in a statement.
He added, “Our 2026–2027 Caribbean voyages aboard Ilma offer the freedom to design a journey perfectly suited to the occasion, with departures from Miami and San Juan creating a flexible, immersive way to experience this extraordinary region.”
Winter 2026–2027 Caribbean Highlights
November 9, 2026 | 4-Night Miami Round Trip to sun-drenched Bahamian islands. Drop anchor off Sandy Point and relax on the yacht’s Marina or set out on paddleboards or kayaks to encounter the diverse marine life in these famously scenic waters. The visit includes the National Art Gallery or rum distilleries in the colorful capital of Nassau before continuing to Bimini with its unparalleled sportfishing.
December 21, 2026 | 7-Night San Juan Round Trip sails from historic San Juan on a voyage to the Southern Caribbean with a day in Guadeloupe swimming and exploring by kayak or paddleboard from the yacht’s Marina platform. Other trip features include the French side of St. Martin. the lush mountains of Dominica, across Anguilla’s pristine beaches and The Baths of Virgin Gorda.
January 19, 2027 | 3-Night San Juan Round Trip offers a three-night Caribbean getaway, sailing roundtrip from San Juan, then dropping anchor in the yacht-filled harbor of St. Barth to explore the beaches and boutiques before heading to the stunning beaches of Virgin Gorda.
February 12, 2027 | 7-Night San Juan Round Trip goes from San Juan’s cobblestone streets to the iconic shallows of The Baths on Virgin Gorda before a visit to St. Barth, relaxing on Antigua’s pristine beaches, exploring the lush mountains of St. Lucia and Canouan’s extensive coral reef, home to vibrant sea life.
This article originally appeared in TravelPulse.
Contact My Journey Begins Travel to book a Ritz-Carlton Yacht sailing this winter 2026-27.