9 reviews | Feb 01, 2025 | Seabourn | Ovation | Caribbean | Bridgetown | Bridgetown | 14 Nights | Antigua | Aruba | Bonaire, Netherlands Antilles | Bridgetown, Barbados | Cartagena, Colombia | Curacao, Netherlands | Isla Catalina, Dominican Republic | Santa Marta, Colombia | Santo Domingo, Dom Rep. | $9,166 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
9 reviews | Feb 01, 2025 | Seabourn | Ovation | Caribbean | Bridgetown | Philipsburg | 21 Nights | Antigua | Aruba | Bonaire, Netherlands Antilles | Bridgetown, Barbados | Cartagena, Colombia | Curacao, Netherlands | Isla Catalina, Dominican Republic | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Santa Marta, Colombia | Santo Domingo, Dom Rep. | St. Lucia | Terre-de-Haut, Guadaloupe | $12,579 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
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: $2,799 $1,799You Save: $1,000 Up To $150 Onboard Credit | 35% | |
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! |
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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 Prepaid Gratuities | 64% | Prepaid Gratuities |
2 reviews | Dec 21, 2024 | Silversea | Silver Moon | Caribbean | Bridgetown | Ft. Lauderdale | 16 Nights | Belize City, Belize | Bequia, Grenadines | Cartagena, Colombia | Colon, Panama | Oranjestad, Aruba | Scarborough, Tobago | Willemstad, Curacao | $11,700 Up To $1000 Onboard Credit | | Suite! |
| Mar 23, 2025 | Silversea | Silver Ray | Caribbean | Bridgetown | Ft. Lauderdale | 9 Nights | Bequia, Grenadines | St. Johns, Antigua | St. Thomas, Virgin Islands | $7,400 Up To $750 Onboard Credit | | Suite! |
10 reviews | Dec 22, 2025 | Silversea | Silver Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Bequia, Grenadines | Philipsburg, St. Maarten | Roseau, Dominica | St. Johns, Antigua | St. Thomas, Virgin Islands | Willemstad, Curacao | $9,300 Up To $1000 Onboard Credit | | |
5 reviews | Dec 28, 2025 | Silversea | Silver Shadow | Caribbean | Bridgetown | Philipsburg | 7 Nights | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $6,500 Up To $750 Onboard Credit | | |
5 reviews | Feb 12, 2026 | Silversea | Silver Shadow | Caribbean | Bridgetown | Philipsburg | 7 Nights | Gustavia, Saint Barthélemy | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | St. Johns, Antigua | $6,100 Up To $750 Onboard Credit | | Balcony! |
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 | Dec 14, 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 | $4,299 Up To $500 Onboard Credit | | 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) |
11 reviews | Dec 21, 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 | $4,499 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) |
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 | 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 | | |
11 reviews | Jan 11, 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 | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | 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) |