37 reviews | Jan 29, 2025 | Oceania | Sirena | Caribbean | Bridgetown | Miami | 10 Nights | Bridgetown | Kingstown | Miami | Nassau | Oranjestad | Port Royal | Willemstad | From: $8,198 $2,790You Save: $5,408 Up To $225 Onboard Credit | 65% | Onboard Credit! |
11 reviews | Jan 18, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 01, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $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) |
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15 reviews | Feb 22, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
47 reviews | Mar 22, 2025 | Azamara | Journey | Caribbean | Bridgetown | Miami | 9 Nights | ANTIGUA | BRIDGETOWN | CASTRIES | MIAMI, FLORIDA | PHILIPSBURG | ROSEAU | SAN JUAN, PUERTO RICO | VIRGIN GORDA | $2,885 Up To $250 Onboard Credit | | Onboard Credit! |
11 reviews | Dec 21, 2024 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,899 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 | $2,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Jan 11, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
9 reviews | Jan 10, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Philipsburg | 7 Nights | Antigua | Bridgetown, Barbados | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | St. Lucia | $3,368 Up To $500 Onboard Credit | | |
9 reviews | Jan 24, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Philipsburg | 7 Nights | Antigua | Bridgetown, Barbados | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | St. Lucia | $3,368 Up To $500 Onboard Credit | | Suite! |
9 reviews | Feb 14, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Philipsburg | 7 Nights | Antigua | Bridgetown, Barbados | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | St. Lucia | $3,368 Up To $500 Onboard Credit | | Suite! |
9 reviews | Feb 28, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Philipsburg | 7 Nights | Antigua | Bridgetown, Barbados | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | St. Lucia | $3,368 Up To $500 Onboard Credit | | Suite! |
| Nov 30, 2024 | SeaDream Yacht Club | SeaDream I | Caribbean | Bridgetown | Marigot | 7 Nights | Bridgetown, Barbados, Barbados | Falmouth Bay, Antigua and Barbuda | Le Marin, Martinique, F.W.I. | Marigot, Saint Martin, F.W.I. | Mayreau, St. Vincent and the Grenadines | Port Elizabeth, Bequia, St. Vincent and the Grenadines | Rodney Bay, Saint Lucia | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $3,499 Up To $500 Onboard Credit | | Onboard Credit! |
| Mar 29, 2025 | SeaDream Yacht Club | SeaDream I | Caribbean | Bridgetown | Philipsburg | 7 Nights | Bridgetown, Barbados, Barbados | Charlestown, Nevis, St. Kitts & Nevis | Gustavia, St. Barths, F.W.I. | Mayreau, St. Vincent and the Grenadines | Philipsburg, Sint Maarten, Dutch Caribbean | Port Elizabeth, Bequia, St. Vincent and the Grenadines | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I. | $3,499 Up To $500 Onboard Credit | | 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) |
6 reviews | Dec 14, 2024 | Star Clippers | Star Clipper | Panama Canal | Bridgetown | Balboa | 14 Nights | Balboa (Isla Flamenco), Panama | Bridgetown, Barbados | Kralendijk, Bonaire | Oranjestad, Aruba | Panama Canal Transit | Santa Marta, Colombia | St. George's, Grenada | Tobago Cays, Grenadines | Willemstad, Curacao | $3,540 Up To $500 Onboard Credit | | |
9 reviews | Mar 14, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Bridgetown | 7 Nights | Bridgetown, Barbados | Rodney Bay, Saint Lucia | Roseau, Dominica | $3,469 Up To $500 Onboard Credit | | Suite! |
9 reviews | Feb 07, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Bridgetown | 7 Nights | Bridgetown, Barbados | Rodney Bay, Saint Lucia | Roseau, Dominica | $3,469 Up To $500 Onboard Credit | | |
9 reviews | Jan 03, 2026 | Seabourn | Ovation | Caribbean | Bridgetown | Bridgetown | 7 Nights | Aruba | Bonaire, Netherlands Antilles | Bridgetown, Barbados | Curacao, Netherlands | Rodney Bay, Saint Lucia | $3,474 Up To $500 Onboard Credit | | |