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14-Night Windstar Caribbean Cruise

Star Collector: Lovely Leeward Islands

Whether you’re passionate about swimming among undersea wildlife or the intricate cultures and intertwined European histories of the Leeward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.

Early Booking Offer – Receive up to $200 onboard credit per stateroom + all-inclusive package + Pay in full at time of booking and save 5% on select 2027-2028 sailings when you book by April 20, 2026*

All-inclusive Package includes:

~Wi-Fi

~Unlimited beer, wine and cocktails

~All Gratuities

Ship: Star Pride | Cruise Line: Windstar| Sail Date: November 1, 2027 | From/To: Roundtrip San Juan | Length: 14-Nights

Ocean View Suite 2 From

$5,333

Per person including all taxes, fees and port expenses

Balcony Suite From

$6,753

Per person including all taxes, fees and port expenses

Star Balcony Suite From

$6,893

Per person including all taxes, fees and port expenses

Deluxe Suite From

$8,993

Per person including all taxes, fees and port expenses

Popular Highlights:

14 Nights | Caribbean Eastern | Windstar: Star Pride
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• Day 1:San Juan
Mon Nov 1, 2027 | Depart 07:00 PM

• Day 2:CRUZ BAY, ST JOHN, Virgin Islands (US)
Tue Nov 2, 2027 | 08:00 AM To 06:00 PM

• Day 3:Basseterre
Wed Nov 3, 2027 | 08:00 AM To 05:00 PM

• Day 4:Gustavia
Thu Nov 4, 2027 | 07:00 AM To 10:00 PM

• Day 5:Philipsburg, St Maarten
Fri Nov 5, 2027 | 08:00 AM To 10:00 PM

• Day 6:Jost Van Dyke, Great Harbour
Sat Nov 6, 2027 | 09:00 AM To 10:00 PM

• Day 7:Virgin Gorda / Prickly Pear, British Virgin Islands
Sun Nov 7, 2027 | 08:00 AM To 05:00 PM

• Day 8:San Juan
Mon Nov 8, 2027 | 07:00 AM To 07:00 PM

• Day 9:Day At Sea
Tue Nov 9, 2027

• Day 10:St Georges
Wed Nov 10, 2027 | 09:00 AM To 10:00 PM

• Day 11:Bequia
Thu Nov 11, 2027 | 08:00 AM To 10:00 PM

• Day 12:Mayreau
Fri Nov 12, 2027 | 08:00 AM To 05:00 PM

• Day 13:Les Saintes
Sat Nov 13, 2027 | 10:00 AM To 05:00 PM

• Day 14:Marigot, St Martin
Sun Nov 14, 2027 | 08:00 AM To 03:00 PM

• Day 15:San Juan
Mon Nov 15, 2027 | Arrive 07:00 AM

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 Cruises and can be eliminated at any time without notice. Promotion is on select 2027 and 2028 sailings. All pricing was as of March 27, 2026, and not guaranteed. Other restrictions may apply. Ships’ registry: Bahamas