15 reviews | Nov 16, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 23, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2024 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $5,199 Up To $750 Onboard Credit | | Onboard Credit! |
24 reviews | Dec 28, 2024 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $5,199 Up To $750 Onboard Credit | | Onboard Credit! |
Need Help Planning A Cruise?
Our cruise experts can help you:
- Find the best discounts
- Hold a cabin for 24 hours for free
- Receive personalized recommendations
- Book handicap accessible cabins
|
24 reviews | Jan 04, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 01, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 14, 2024 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 28, 2024 | Windstar | Star Pride | Caribbean - Southern | Balboa | Bridgetown | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Jan 11, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Feb 22, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Nov 19, 2024 | Windstar | Wind Star | Central America | Bridgetown | Puerto Caldera | 18 Nights | Balboa / Fuerte Amador | Bequia | Bridgetown | Cartagena | Colón | Golfo Dulce | Isla Parida | Kralendijk | Mayreau | Oranjestad | Puerto Caldera | Quepos | St. George's | Willemstad | $6,599 Up To $750 Onboard Credit | | |
10 reviews | Dec 14, 2024 | Windstar | Wind Star | Central America | Colon | Puerto Caldera | 14 Nights | Bahia Herradura | Balboa / Fuerte Amador | Colón | Corinto | Golfo Dulce | Isla Parida | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $5,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Dec 21, 2024 | Windstar | Wind Star | Central America | Puerto Caldera | Colon | 14 Nights | Bahia Herradura | Balboa / Fuerte Amador | Colón | Corinto | Golfo Dulce | Isla Parida | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $6,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Jan 02, 2025 | Windstar | Star Breeze | Central America | Papeete | Puerto Caldera | 14 Nights | Papeete | Puerto Caldera | $2,099 Up To $250 Onboard Credit | | |
10 reviews | Jan 11, 2025 | Windstar | Wind Star | Central America | Puerto Caldera | Colon | 14 Nights | Bahia Herradura | Balboa / Fuerte Amador | Colón | Corinto | Golfo Dulce | Isla Parida | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $4,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |