Small Ship Caribbean Cruises
Let Your Soul Dance
If you could design the perfect island itinerary it would look a lot like these. Ports of call would include tiny towns and hidden harbors known only to private yachts and small ships like ours. Schedules would allow for dropping the Watersports Platform in turquoise bays and raising sails on the way to your next island rendezvous. And the laid-back island vibe would continue on board with a mouthwatering Signature Onboard Barbecue by the pool.
Best of all, on every cruise there would be one day that was even more special than the rest, when you land on a secluded beach for Windstar’s Signature Beach Party, elaborate buffet and watersports included.
Only Windstar Brings You Close Enough
Star Collector: Fall Leaves & Caribbean Breezes
Date and Duration
9th October 2026 (19 Nights)
Port to Port
Montréal, Québec to San Juan (Puerto Rico)
Ship
Star Pride
Mind, Body and Spirit Collection: Bermuda Bliss
Date and Duration
20th October 2026 (8 Nights)
Port to Port
Boston, Massachusetts to San Juan (Puerto Rico)
Ship
Star Pride
Masterpieces at Sea: Gems of the Leeward Islands
Date and Duration
28th October 2026 (11 Nights)
Port to Port
San Juan (Puerto Rico) to San Juan (Puerto Rico)
Ship
Star Pride
Star Collector: Lovely Leewards
Date and Duration
8th November 2026 (14 Nights)
Port to Port
San Juan (Puerto Rico) to San Juan (Puerto Rico)
Ship
Star Pride
Windward Islands Surf & Sunsets
Date and Duration
8th November 2026 (7 Nights)
Port to Port
San Juan (Puerto Rico) to San Juan (Puerto Rico)
Ship
Star Pride
Star Collector: Southern Caribbean Thanksgiving Jubilee
Date and Duration
10th November 2026 (25 Nights)
Port to Port
Lisbon to Colón
Ship
Wind Star