Windstar Cruises Is Sending Its Next Caribbean Ship to Puerto Rico 

Windstar Cruises is charting an expansion of its boutique fleet, adding two all-suite Star Class vessels as it looks to capture a growing appetite for small-ship luxury. Star Seeker, the first in the series, is slated to debut in December 2025 with a Transatlantic maiden voyage, followed by a Caribbean christening sailing from Miami on January 15. Sister ship Star Explorer will follow in December 2026.

Each vessel will carry 224 passengers across 112 suites, all outfitted with either private verandas or panoramic infinity windows. 

The ships will also debut a new accommodation category: the Horizon Owner’s Suites, located aft and featuring expansive wrap-around balconies. With a 1:2 staff-to-guest ratio, Windstar is doubling down on its promise of personalized, high-touch service, aiming to lure travelers seeking an intimate, yacht-like experience at sea.

So where will Star Seeker be heading in the Caribbean? 

The first cruise is an eight-day from Miami to San Juan, Puerto Rico (prices start at $5,849, with $6,641 per person all-inclusive). 

Star Seeker will be home-porting in Puerto Rico beginning in mid-January 2026. That includes, for example, a seven-day San Juan and the Virgin Islnds cruise that starts at $3,699 cruise-only and $4,392 all-inclusive. 

Windstar often emphasizes ports that larger ships skip, leaning into that “yacht-like” experience that’s become one of the hottest trends in travel in the last few years. 

The other standout, particularly from our experience is the quality of Windstar’s shore excursions. You might have a special barbecue on the beach on a deserted island in the British Virgin Islands. That’s without mentioning the brand’s iconic “sail aways.”