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
Great Harbour, Jost van Dyke Cruise Port
Cruise sailings that call at Great Harbour, Jost van Dyke, with route previews and links into Tripbase where destination coverage exists.
Inventory snapshot
21
sailings call here
Ashore in Great Harbour, Jost van Dyke
Loading port chart...
On the chart
Sailings that call at Great Harbour, Jost van Dyke
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: 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
Ocean CrossingTransatlantic
- Sails Nov 5, 2027 · 15 nights
- Wind Surf
- From LISBON → PHILIPSBURG, ST. MAARTEN
Ocean view $2,580 · Suite $8,130 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
Ocean Crossing16% vs 4 weeks agoTransatlantic
- Sails Dec 6, 2027 · 14 nights
- Star Legend
- From CADIZ → SAN JUAN
Ocean view $4,380 · Balcony $9,280 · Suite $13,480 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