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
Gustavia, St. Barthelemy Cruise Port
Gustavia is the main town and capital of the island of Saint Barthélemy. Originally called Le Carénage, it was renamed in honor of King Gustav III of Sweden.
Image via Wikimedia CommonsInventory snapshot
23
sailings call here
Ashore in Gustavia, St. Barthelemy
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On the chart
Sailings that call at Gustavia, St. Barthelemy
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
Classic CaribbeanCaribbean
- Sails Dec 26, 2026 · 7 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $4,742 · Suite $7,332 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
Classic CaribbeanCaribbean
- Sails Nov 28, 2027 · 7 nights
- Wind Surf
- From PHILIPSBURG, ST. MAARTEN · roundtrip
Ocean view $2,537 · Suite $5,442 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