San Juan & the Virgin Islands
GO ALL IN
Go All In
Drinks, gratuities, and WiFi included plus up to 40% off selected sailings.
7 nights
Star Pride
15 Nov '26Cruise overview
Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Bypass the major cruise terminals in favor of exclusive marinas and anchorages on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant ship is already there.
Itinerary
San Juan (Puerto Rico)
If you associate Puerto Rico’s capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island’s nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico (“rich port”).Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico’s administrative and population center remained firmly in Spain’s hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.
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At sea
Basseterre, Saint Kitts
Gustavia
Philipsburg
Great Harbour, Jost Van Dyke
At sea
San Juan (Puerto Rico)
Star Porthole Suite
The Star Porthole Suite offers cosy sophistication with charming porthole windows providing a classic maritime feel. Well-appointed and thoughtfully designed, these suites feature comfortable sleeping and sitting areas, ideal for guests seeking intimate, elegant accommodation without compromising on Windstar’s renowned luxury and service.
Amenities
- Queen or Twin Configuration
- Shower
- Room Service Available
- TV
- Safe
- Hair Dryer
- Telephone
- Desk
- Lounge Area
- Mini Bar (Additional Cost)
- Wi-Fi (Additional Cost)
Ship features
Star Pride offers suite-only luxury, refreshed venues and modern amenities tailored for boutique cruising.
- Completely all-suite ship after Star Plus refit
- New dining options: Cuadro 44, Star Grill
- Infiniti pool with ocean views
- Watersports platform with complimentary use of kayaks and paddleboards
- Open-bridge access for guests
- Refreshed lounges, spa, fitness facilities and library
- Beauty salon, boutique, destination office and screening room
- Low-key evening entertainment and local music
