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7-Day Windstar Classic Caribbean Cruise

7-Day Caribbean Cruise: San Juan & The Virgin Islands

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 like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.

March Offer: Receive all-inclusive package + up to $2,000 onboard credit per stateroom/suite + pre-cruise hotel night + transfers on select sailings through March 2027 when you book by March 31, 2026*

All inclusive package includes:

~WiFi

~Unlimited beer, wine and cocktails

~All gratuities

Ship: Star Pride| Cruise Line: Windstar| Sail Date: November 29, 2026 | From/To: Roundtrip San Juan, Puerto Rico | Length: 7-Nights

Ocean View Suite From

$3,602

Per person including all taxes, fees and port expenses

Balcony Suite From

$4,422

Per person including all taxes, fees and port expenses

Star Balcony Suite From

$4,462

Per person including all taxes, fees and port expenses

Balcony Suite 1 From

$4,662

Per person including all taxes, fees and port expenses

Are you traveling solo? Ask our agents about Windstar’s Reduced single supplements on select 2026 sailings!

Popular Highlights:

  • In San Juan, admire the incredible views from El Morro’s 16th-century ramparts, a UNESCO World Heritage Site.
  • Shop Gustavia's duty-free boutiques or grab a glass of the island’s signature ti' punch at a beachside bar
  • Mingle with the glitterati in St. Barts.
  • Take a stroll in the St. John’s National Park, which covers over half of the islands.
  • Let the Bubbly Pool on Jost Van Dyke wash your cares away.
Date Day Port Arrive Depart
Nov. 29, 2026 Sun. San Juan, Puerto Rico 7:00pm
Nov. 30, 2026 Mon. Cruz Bay, St. John, Virgin Islands (U.S.) 8:00am 6:00pm
Dec. 1, 2026 Tues. Gustavia 8:00am 10:00pm
Dec. 2, 2026 Wed. Basseterre, St. Kitts 8:00am 5:00pm
Dec. 3, 2026 Thurs. Philipsburg, St. Maarten 8:00am 10:00pm
Dec. 4, 2026 Fri. Jost Van Dyke, Great Harbour 9:00am 10:00pm
Dec. 5, 2026 Sat. Virgin Gorda, Prickly Pear, British Virgin Islands 8:00am 5:00pm
Dec. 6, 2026 Sun. San Juan, Puerto Rico 7:00am

Star Pride

All-Suite Yacht

Serving just 312 guests, Star Pride is the perfect size — small enough to offer the unique experiences that set Windstar apart (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.

This intimate all-suite yacht features spacious ocean-view accommodations. On board, you’ll find a fully equipped fitness center, a spa with complimentary sauna, two full-service bars, on-deck hot tubs, a water-access marina, and much more.

And did we mention all dining is included? From gourmet bites at our Yacht Club Café to specialty restaurants like Basil + Bamboo, our award-winning cuisine is always complimentary so you can indulge freely.

Ready to experience Star Pride for yourself? Join us on one of her voyages across the world — and get ready to sail beyond ordinary.

*Prices are in USD, per person based on double occupancy, availability and subject to change without notice. All cruise taxes, fees and port expenses are included in the above pricing. All promotions are capacity controlled by Windstar and can be eliminated at any time without notice. Onboard credit amount is based on number of sailing nights and stateroom category. Promotion is for all sailings departing through March 31, 2027; excludes Grand Prix, Mystery Cruises, Eclipse Cruises, Star Seeker and Star Explorer Maiden Voyages , any accompanying Star Collector voyage, and all 5 nights or less sailings. Other restrictions may apply. Ships’ registry: Bahamas