Windstar Cruises
Masterpieces at Sea: Gems of the Leeward Islands22% vs 4 weeks agoCaribbean
- Sails Oct 28, 2026 · 11 nights
- Star Pride
- From SAN JUAN · roundtrip
Ocean view $3,908 · Balcony $7,153 · Suite $9,628 per person
port
Virgin Gorda/Prickly Pear, BVI Cruise Port
Cruise sailings that call at Virgin Gorda/Prickly Pear, BVI, with route previews and links into Tripbase where destination coverage exists.
Inventory snapshot
21
sailings call here
Ashore in Virgin Gorda/Prickly Pear, BVI
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On the chart
Sailings that call at Virgin Gorda/Prickly Pear, BVI
Windstar Cruises
Star Collector: Lovely Leewards40% vs 4 weeks agoCaribbean
- Sails Nov 8, 2026 · 14 nights
- Star Pride
- From SAN JUAN · roundtrip
Ocean view $4,434 · Balcony $8,634 · Suite $10,244 per person
Windstar Cruises
San Juan & the Virgin Islands51% vs 4 weeks agoCaribbean
- Sails Nov 15, 2026 · 7 nights
- Star Pride
- From SAN JUAN · roundtrip
Ocean view $2,443 · Balcony $4,263 · Suite $4,753 per person
Windstar Cruises
Beach Fun & Sun: A Remote Caribbean Getaway9% vs 4 weeks agoCaribbean
- Sails Dec 19, 2026 · 7 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $3,708 · Suite $6,123 per person
Windstar Cruises
Star Collector: Caribbean ExplorationsCaribbean
- Sails Dec 19, 2026 · 14 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $8,030 · Suite $12,790 per person
Windstar Cruises
Star Collector: Fall Leaves & Caribbean BreezesCanada & New England
- Sails Oct 11, 2027 · 21 nights
- Star Pride
- From MONTREAL, QC → SAN JUAN
Ocean view $9,153 · Balcony $14,823 · Suite $20,598 per person
Windstar Cruises
Bermuda BlissCaribbean
- Sails Oct 22, 2027 · 10 nights
- Star Pride
- From BOSTON, MA → SAN JUAN
Ocean view $4,527 · Balcony $8,727 · Suite $11,727 per person
Windstar Cruises
Star Collector: Bermuda & Caribbean Island ExplorerCaribbean
- Sails Oct 22, 2027 · 17 nights
- Star Pride
- From BOSTON, MA → SAN JUAN
Ocean view $6,210 · Balcony $11,820 · Suite $16,155 per person
Windstar Cruises
Star Collector: Hearty Ports & Rum Punches - A Transatlantic CrossingTransatlantic
- Sails Nov 5, 2027 · 23 nights
- Wind Surf
- From LISBON → PHILIPSBURG, ST. MAARTEN
Ocean view $4,813 · Suite $12,058 per person
Windstar Cruises
Beach Fun & Sun: A Remote Caribbean GetawayCaribbean
- Sails Nov 20, 2027 · 8 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $3,028 · Suite $5,988 per person
Windstar Cruises
Star Collector: Caribbean ExplorationsCaribbean
- Sails Nov 20, 2027 · 15 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $4,845 · Suite $9,795 per person
Windstar Cruises
Beach Fun & Sun: A Remote Caribbean GetawayCaribbean
- Sails Dec 5, 2027 · 7 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $2,868 · Suite $5,773 per person
Windstar Cruises
Star Collector: Atlantic Crossing to the Virgin Islands12% vs 4 weeks agoTransatlantic
- Sails Dec 6, 2027 · 21 nights
- Star Legend
- From CADIZ → SAN JUAN
Ocean view $5,563 · Balcony $11,023 · Suite $16,063 per person
Windstar Cruises
Star Collector: Caribbean ExplorationsCaribbean
- Sails Dec 27, 2027 · 13 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $4,280 · Suite $8,505 per person
Windstar Cruises
Beach Fun & Sun: A Remote Caribbean GetawayCaribbean
- Sails Jan 3, 2028 · 6 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $2,108 · Suite $4,508 per person
Windstar Cruises
Star Collector: Costa Rica, Panama & ArubaPanama Canal
- Sails Feb 21, 2028 · 21 nights
- Star Pride
- From PUERTO CALDERA, SAN JOSE' → SAN JUAN
Ocean view $7,837 · Balcony $11,932 · Suite $17,287 per person
Windstar Cruises
Star Collector: Panama, Aruba & the British Virgin IslandsPanama Canal
- Sails Feb 28, 2028 · 14 nights
- Star Pride
- From FUERTE AMADOR, PANAMA CITY → SAN JUAN
Ocean view $5,535 · Balcony $8,405 · Suite $11,975 per person
Windstar Cruises
Island Trails: Aruba to the Virgin Islands14% vs 4 weeks agoCaribbean
- Sails Mar 6, 2028 · 7 nights
- Star Pride
- From ORANJESTAD, ARUBA → SAN JUAN
Ocean view $2,754 · Balcony $4,924 · Suite $7,024 per person
Windstar Cruises
Star Collector: Windward Islands, ABC Islands & the Virgin Island9% vs 4 weeks agoCaribbean
- Sails Mar 6, 2028 · 14 nights
- Star Pride
- From ORANJESTAD, ARUBA → SAN JUAN
Ocean view $4,500 · Balcony $7,300 · Suite $10,870 per person
Windstar Cruises
Star Collector: Caribbean Collection: ABC, BVI & the Windwards6% vs 4 weeks agoCaribbean
- Sails Mar 6, 2028 · 21 nights
- Star Pride
- From ORANJESTAD, ARUBA → SAN JUAN
Ocean view $6,663 · Balcony $10,443 · Suite $15,798 per person
Windstar Cruises
Star Collector: Hearty Ports & Rum Punches - A Transatlantic CrossingTransatlantic
- Sails Mar 12, 2028 · 22 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN → LISBON
Ocean view $4,388 · Suite $10,218 per person