If you thought sailing to small islands and boutique harbors in idyllic tropical places was just for billionaires in their private yachts, think again. Even you can feel like a billionaire on one of Emerald Cruises’ two new mega-yachts.

We sailed aboard the Emerald Sakara on a ‘yachtsman’s itinerary’ from San Juan, Puerto Rico, weaving through the U.S. and British Virgin Islands to St. Kitts and St. John’s, Antigua. And even if you’ve cruised the Caribbean many times before, this is an all-new cruise experience!

WATCH THE VIDEO ABOVE: A conversation with Emerald Sakara’s Captain Rob on the bridge about what makes yacht cruising in the Caribbean a game-changing way to cruise.

GOOD NEWS! Both Emerald Yachts Sailing the Caribbean for the Winter 2025-26 Season

Now you have double the options for sailing on an Emerald Cruises yacht in the Caribbean. The cruise line’s award-winning superyacht, Emerald Azzurra, is returning to the Caribbean for the Winter 2025-2026 season, joining her sister yacht, Emerald Sakara, on cruises to the region’s secluded ports and picturesque coves between December 2025 and March 2026.

Setting sail weekly from San Juan, Puerto Rico to St. John’s, Antigua, Emerald Azzurra takes guests to explore the region’s secluded ports and picturesque coves on one of two curated itineraries: the tranquil and charming ‘Caribbean Yachting Hideaways’ and the culturally rich ‘Caribbean Yachting Discovery’, each designed to offer an unparalleled yachting experience.

The yachting approach is finding lots of fans! Emerald Cruises’ decision to redeploy Emerald Azzurra comes in response to the overwhelming success of its yacht cruises to date, along with growing demand for intimate, luxury cruise travel. We should note that the change replaces the previously planned Red Sea and Seychelles itineraries.

Emerald Azzura’s Caribbean Itineraries

Emerald Azzurra will sail weekly between San Juan, Puerto Rico, and St. John’s, Antigua, calling on intimate ports and coves along the way.

On the Caribbean Yachting Hideaways route, guests will enjoy idyllic stops at destinations like Culebra’s azure waters, the charming town of Esperanza on Vieques Island, and the tranquil beaches of Cruz Bay on St. John, USVI. Additional highlights include Virgin Gorda and Gustavia on the exquisitely chic jet-setter French island of Saint Barthélemy (that’s St. Bart’s to you!)

On the Caribbean Yachting Discovery itinerary, guests will enjoy a mix of natural beauty and vibrant culture, ideally suited to the superyacht’s intimate design.

Emerald Cruises has even designed these itineraries so those of us craving a double dose of island-hopping yacht cruising can book consecutive (back-to-back) week-long sailings with only one repeating port.

During the same season, sister yacht Emerald Sakara will also sail weekly throughout the Caribbean between Bridgetown, Barbados and Marigot, St. Martin.

Spring Mediterranean Yacht Itineraries

Pre- and post-winter season, both yachts will return to the Mediterranean in April 2026, offering newly expanded autumn and spring itineraries, including Historical Echoes, a voyage from Larnaca to Athens and Mediterranean Crossroads, from Athens to Valletta, Malta. These itineraries are designed to provide guests with a deeper cultural and culinary immersion in the region’s most alluring destinations.