Goldie's Xplorations
(312) 221-8375 | goldiesxplorations@gmail.com

SAN JUAN & THE VIRGIN ISLANDS on Star Pride

Cruise, Ocean cruise, Small Ship/Yacht
Star Pride New York
Exterior view of Star Pride sailing near Manhattan, New York
  • Exterior view of Star Pride sailing near Manhattan, New York
  • Exterior view of Star Pride beyond palm trees in Mayreau
  • View of Star Pride crossing the Corinth Canal in Greece
  • View of bed and balcony in Star Pride suite - Photo Credit: Gil Stose Photography
  • View of dining table and living area in Star Pride suite - Photo Credit: Gil Stose Photography
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. Skip more common and commercial ports in favor of less-visited destinations like Montserrat. 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.
About Star Pride
About Windstar Cruises
Windstar Cruises logo

THE WORLD'S BEST SMALL SHIP CRUISE LINE

All cruise ships let you see the world. Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.

Nov 15, 2026 through
Nov 22, 2026
Nov 9, 2026 7:00 PM
7 Nights from
$2,499.00 (USD)
Per Person
+ $63.00 taxes/fees
Category sp
Nov 16, 2025 through
Nov 23, 2025
Nov 10, 2025 7:00 PM
7 Nights from
$2,599.00 (USD)
Per Person
+ $63.00 taxes/fees
Category sp
Jan 10, 2027 through
Jan 17, 2027
Jan 4, 2027 7:00 PM
7 Nights from
$2,599.00 (USD)
Per Person
+ $63.00 taxes/fees
Category sp

Itinerary

Day Port Arrive Depart
1 San Juan 7:00 PM
2 CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) 8:00 AM 6:00 PM
3 Basseterre 8:00 AM 5:00 PM
4 Gustavia 7:00 AM 10:00 PM
5 Philipsburg, St. Maarten 8:00 AM 10:00 PM
6 Jost Van Dyke, Great Harbour 9:00 AM 10:00 PM
7 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
8 San Juan 7:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.