50 reviews | Dec 12, 2024 | Oceania | Insignia | Caribbean | Bridgetown | Miami | 10 Nights | Bridgetown | Castries | Gustavia | Kingstown | Miami | Puerto Plata | Roseau | San Juan | St. George's | St. John's | From: $5,598 $1,799You Save: $3,799 Up To $175 Onboard Credit | 67% | |
15 reviews | Mar 29, 2025 | Windstar | Star Pride | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | The Pitons | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
47 reviews | Nov 15, 2025 | Azamara | Quest | Caribbean - Eastern | Bridgetown | Bridgetown | 14 Nights | BASSETERRE | BEEF ISLAND, TORTOLA | BRIDGETOWN | CASTRIES | CHARLESTOWN | PHILIPSBURG | PORT ELIZABETH, BEQUIA | ROSEAU | SAN JUAN, PUERTO RICO | SCARBOROUGH, TOBAGO | ST. JOHN'S, ANTIGUA | ST. PIERRE | VIRGIN GORDA | $2,319 Up To $350 Onboard Credit | | Onboard Credit! |
47 reviews | Nov 29, 2025 | Azamara | Quest | Caribbean - Eastern | Bridgetown | Bridgetown | 14 Nights | BASSETERRE | BEEF ISLAND, TORTOLA | BRIDGETOWN | CASTRIES | CHARLESTOWN | PHILIPSBURG | PORT ELIZABETH, BEQUIA | ROSEAU | SAN JUAN, PUERTO RICO | SCARBOROUGH, TOBAGO | ST. JOHN'S, ANTIGUA | ST. PIERRE | VIRGIN GORDA | $2,319 Up To $350 Onboard Credit | | Onboard Credit! |
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11 reviews | Jan 25, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
47 reviews | Dec 13, 2025 | Azamara | Quest | Caribbean - Eastern | Bridgetown | Bridgetown | 14 Nights | BASSETERRE | BRIDGETOWN | CASTRIES | CHARLESTOWN | CHARLOTTE AMALIE, ST. THOMAS | PHILIPSBURG | PORT ELIZABETH, BEQUIA | ROSEAU | SAN JUAN, PUERTO RICO | SCARBOROUGH, TOBAGO | ST. JOHN'S, ANTIGUA | ST. PIERRE | VIRGIN GORDA | $2,480 Up To $350 Onboard Credit | | Onboard Credit! |
50 reviews | Feb 22, 2026 | Oceania | Insignia | Caribbean | Bridgetown | Tampa | 9 Nights | Bridgetown | Costa Maya | Cozumel | Montego Bay | Oranjestad | Tampa | From: $6,998 $2,499You Save: $4,499 Up To $250 Onboard Credit | 64% | Onboard Credit! |
11 reviews | Dec 14, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | $2,499 Up To $250 Onboard Credit | | Onboard Credit! |
11 reviews | Jan 11, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Mar 07, 2026 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Mar 21, 2026 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Up To $300 Onboard Credit | | Onboard Credit! |
11 reviews | Dec 28, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 08, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
37 reviews | Jan 29, 2025 | Oceania | Sirena | Caribbean | Bridgetown | Miami | 10 Nights | Bridgetown | Kingstown | Miami | Nassau | Oranjestad | Port Royal | Willemstad | From: $8,198 $3,099You Save: $5,099 Up To $250 Onboard Credit | 62% | Onboard Credit! |
11 reviews | Nov 18, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 07, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 04, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $3,999 Up To $500 Onboard Credit | | Onboard Credit! |
11 reviews | Jan 18, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 28, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |