The Ritz-Carlton Yacht Collection has announced its winter 2026-27 Caribbean season aboard Ilma, now open for reservations. From November 2026 through April 2027, the yacht will sail more than 20 itineraries spanning three to seven nights. This season introduces an expanded selection of shorter three- and four-night Caribbean escapes.
For the first time, Miami joins San Juan as a featured turnaround port. Guests can begin and end their journey in the city, taking advantage of its restaurants, rooftop bars and cultural hotspots before or after their cruise. With abundant direct flight options and the port just 15 minutes from Miami International Airport, the new embarkation point makes a warm-weather retreat to the Caribbean more seamless than ever.
From the cosmopolitan glamor of St. Barth’s Gustavia to the unspoiled charm of Bequia, the season’s itineraries showcase the many facets of the Caribbean. Guests can snorkel colorful reefs in the Virgin Islands, sail into secluded bays in the Grenadines, stroll Antigua’s historic English Harbour or shop for spices and vanilla in the markets of Martinique. Journeys might wind through rainforest roads in St. Lucia or pause on palm-fringed islands like Canouan and Jost Van Dyke, where small harbors welcome yachts far from the bustle of large cruise ports.
The season also invites guests to make the holidays truly memorable at sea. A seven-night Thanksgiving departure from Miami to San Juan offers families the chance to gather against the backdrop of the Caribbean Sea. Roundtrip sailings from San Juan feature festive onboard programming paired with lively island visits for a uniquely Caribbean holiday experience. Guests can welcome 2027 during a New Year’s Eve celebration at the Sandy Lane Yacht Club in St. Vincent & the Grenadines or escape for a Valentine’s Day getaway, where secluded beaches and sweeping sunsets create the perfect setting for connection and meaningful moments. Here are a few highlights of the winter 2026-27 Caribbean itineraries:
- Four-night Miami roundtrip, (November 9, 2026) – Relax into vacation on your private terrace as you sail for 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 diverse marine life. Then visit the National Art Gallery or rum distilleries in the colorful capital of Nassau before continuing to laid-back Bimini, where sportfishing draws visitors from all over the world.
- Seven-night San Juan roundtrip, (December 21, 2026) – Sail from San Juan on a voyage to the gems of the Southern Caribbean. Guadeloupe sets the scene for a day spent swimming and exploring by kayak or paddleboard from the yacht’s Marina platform. From the French side of St. Martin to the lush mountains of Dominica and across Anguilla’s miles of beaches and Virgin Gorda’s iconic granite boulders of The Baths, this is a holiday getaway unlike the rest.
- Three-night San Juan roundtrip, (January 19, 2027) – Sail from San Juan, a city of UNESCO-listed fortresses, art museums and an enchanting Old Town. Drop anchor in the yacht-filled harbor of St. Barth to explore its beaches and boutiques. Then visit the beaches of Virgin Gorda, where volcanic geology has created a striking shoreline of granite boulders and turquoise grottoes.
- Seven-night San Juan roundtrip, (February 12, 2027) – From San Juan’s cobblestone streets to the iconic shallows of The Baths on Virgin Gorda, this is a voyage that encompasses awe-inspiring nature with the charms of island life. After shopping the boutiques and designer galleries on St. Barth, relax on Antigua’s beaches. The lush mountains of St. Lucia await adventurous hikers, while Canouan’s extensive coral reef is home to vibrant sea life.
Each itinerary aboard Ilma is enriched with a range of shore excursions. Travelers can snorkel alongside sea turtles in St. John or the British Virgin Islands, speed across shimmering waters on a private boat before soaring over St. Lucia’s iconic Pitons by helicopter or explore St. Barth’s marine life on an expert-led scuba adventure. On Antigua, a cooking class led by a Michelin-starred team immerses travelers in the flavors of the West Indies, while Virgin Gorda’s legendary Baths reveal hidden tidal pools for a day of exploration.
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