Ritz-Carlton Yacht Collection Caribbean 2026 to 2027

Published on Sep 2, 2025, 4:35 pm CDT

5 min read

The Ritz-Carlton Yacht Collection has released Winter 2026 to 2027 Caribbean sailings aboard Ilma, opening voyages from November 2026 through April 2027. The season adds Miami as a featured turnaround port alongside San Juan, and expands quick-escape options with new three and four night itineraries. Highlights include Thanksgiving and New Year's departures, plus seven night round trips from Puerto Rico visiting marquee islands like St. Barth, Antigua, St. Lucia, Martinique, and the Virgin Islands.

Key Points

Why it matters: Premium small-ship capacity rises, giving luxury travelers more flexible winter choices.
Travel impact: Miami and San Juan turnarounds simplify air-sea connections for U.S. flyers.
What's next: Early demand will likely center on holiday weeks and newly added short getaways.
Fleet notes:** Ilma carries 448 guests in 224 suites, each with a private terrace.
Competitive lens:** Targets the same yacht-style niche as SeaDream, Emerald, and Four Seasons.

Snapshot

Ritz-Carlton's Ilma will operate more than 20 Caribbean itineraries between November 2026 and April 2027, with lengths from three to seven nights. For the first time, Miami joins San Juan as a featured turnaround port, positioning the program for easy long-weekend escapes and family holiday weeks. Sample calls include Nassau and Bimini on short Bahamian runs, plus Guadeloupe, Dominica, St. Barth, Anguilla, Virgin Gorda, Antigua, Martinique, and St. Lucia on seven night sailings. Programming emphasizes marina-deck water sports, curated shore excursions, and festive events like a New Year's Eve celebration in the Grenadines. Bookings are open.

Background

The Ritz-Carlton Yacht Collection debuted in 2022 with Evrima, added Ilma in 2024, and introduced Luminara in 2025. The brand has steadily widened its map, including a recently announced South Pacific and Asia slate for Winter 2026 to 2027, and a European build-out for Summer 2026. For context on the fleet's direction and onboard product, see our coverage of Luminara's maiden season, Ritz-Carlton Luminara Sets Sail on First Voyage, Raising the Bar, and the line's wider winter expansion, Ritz-Carlton Yacht Collection Sails French Polynesia. Ilma measures 790 feet, accommodates up to 448 guests, and features an expanded marina, five restaurants by Fabio Trabocchi and Michael Mina, and one of the highest space-to-guest ratios at sea. The Caribbean program builds on that platform with shorter itineraries and two convenient homeports.

Latest Developments

Miami added as a featured turnaround port

For Winter 2026 to 2027, Miami becomes a featured turnaround port alongside San Juan. The port's proximity to Miami International Airport (MIA) and dense flight network reduces total trip time and widens same-day arrival options, especially for three and four night escapes. From Miami, Ilma will offer quick Bahamian loops, including Nassau and Bimini, with marina-deck time for kayaking and paddleboarding. The program also schedules a seven night Thanksgiving sailing from Miami to San Juan, creating a one-way holiday option that pairs city stays with island time. San Juan departures focus on the Southern and Northeastern Caribbean, balancing boutique harbors with well-known beach stops to keep tender times short and port days long.

Shorter getaways broaden premium access

The schedule introduces additional three and four night sailings round trip San Juan, aimed at travelers seeking a long-weekend luxury cruise that still delivers signature yacht experiences. Those short runs prioritize St. Barth's Gustavia for shopping and beaches, and Virgin Gorda for The Baths, while seven night round trips add Guadeloupe, Dominica, Anguilla, Antigua, Martinique, and St. Lucia. Onboard, Ilma's terrace-only suite mix, open-air lounges, and a mezzanine marina platform emphasize an outdoor-first Caribbean feel. Shore programming leans toward small-group culinary classes, guided snorkeling with turtles, and private-boat days capped by helicopter sightseeing where available. Holiday itineraries include festive onboard events and a New Year's Eve celebration in St. Vincent and the Grenadines.

Analysis

This release shows Ritz-Carlton leaning into two trends that have reshaped upscale cruising since 2022. First, shorter premium itineraries continue to win share as affluent travelers mix quick getaways with longer annual trips. Adding more three and four night options aligns Ilma with SeaDream's and Emerald's bite-size Caribbean menus, while preserving the line's service cadence and marina-forward days at anchor. Second, airport-rail-port friction is now a booking-stage dealbreaker. Miami's inclusion as a featured turnaround, paired with San Juan, speaks directly to lift, schedule reliability, and fewer connections. Miami International Airport (MIA) and Luis Muñoz Marín International Airport (SJU) both offer strong domestic reach, which helps weekenders arrive before embarkation without a buffer night.

For the competitive set, Ilma's space ratio and all-suite terraces remain differentiators, especially on short runs where open-deck time competes with port hours. Itineraries that pair St. Barth cachet with Virgin Gorda's natural draw should convert first, followed by holiday weeks and Valentine's pairings. Pricing and air packages were not detailed in the announcement, so advisors will watch for bundled offers and loyalty hooks via Marriott Bonvoy. The risk is capacity clustering around the Northeastern Caribbean, where many small ships now overlap. However, Ilma's marina and curated excursions keep the focus on yacht-style days rather than port counts, which is the right strategic fit for this segment.

Final Thoughts

By adding Miami turnarounds and increasing short sailings, Ritz-Carlton sharpens its Caribbean value proposition for Winter 2026 to 2027. The program emphasizes easy access, terrace-only suites, and marina-deck time that feels purpose-built for warm-weather weekends. Expect early bookings to center on holiday sailings and three to four night escapes, with seven night San Juan round trips anchoring the rest of the season. For travelers who want a resort-level experience at sea without committing to a long itinerary, Ilma's schedule hits the sweet spot. That positioning strengthens the Ritz-Carlton Yacht Collection Caribbean portfolio.