15 reviews | Dec 07, 2025 | Windstar | Star Pride | Caribbean | San Juan | Colon | 6 Nights | Cartagena | Colón | San Blas | San Juan | Santo Domingo | $2,899 Up To $300 Onboard Credit | | Suite! |
36 reviews | Jan 03, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 10 Nights | Basseterre | Fort De France | Gustavia | Kingstown | Pointe A Pitre | Roseau | San Juan | St. George's | St. John's | From: $15,998 $5,099You Save: $10,899 Up To $750 Onboard Credit | 68% | Suite! |
36 reviews | Jan 13, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 7 Nights | Castries | Charlotte Amalie | Gustavia | Philipsburg | Roseau | San Juan | St. John's | From: $12,898 $4,049You Save: $8,849 Up To $500 Onboard Credit | 68% | Suite! |
36 reviews | Jan 20, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 10 Nights | Basseterre | Fort De France | Gustavia | Kingstown | Pointe A Pitre | Roseau | San Juan | St. George's | St. John's | From: $15,998 $5,099You Save: $10,899 Up To $750 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | 68% | *Distinctive Voyage |
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36 reviews | Jan 30, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 7 Nights | Castries | Charlotte Amalie | Frederiksted | Gustavia | Roseau | San Juan | St. John's | From: $11,998 $3,599You Save: $8,399 Up To $500 Onboard Credit | 70% | Suite! |
36 reviews | Feb 06, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | Miami | 11 Nights | Basseterre | Bonaire (Kralendijk) | Miami | Oranjestad | Philipsburg | Puerto Plata | San Juan | Tortola | Willemstad | From: $17,498 $6,149You Save: $11,349 Up To $750 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | 64% | *Distinctive Voyage |
123 reviews | Nov 23, 2025 | Norwegian | Epic | Caribbean | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Philipsburg St Maarten, Netherland Antilles | San Juan, PR | St Johns Antigua | St Lucia, Saint Lucia | St Thomas, VI | Tortola, British Virgin Islands | $829 Up To $75 Onboard Credit | | |
123 reviews | Nov 30, 2025 | Norwegian | Epic | Caribbean | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Philipsburg St Maarten, Netherland Antilles | San Juan, PR | St Johns Antigua | St Lucia, Saint Lucia | St Thomas, VI | Tortola, British Virgin Islands | $699 Up To $75 Onboard Credit | | Onboard Credit! |
123 reviews | Dec 07, 2025 | Norwegian | Epic | Caribbean | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Philipsburg St Maarten, Netherland Antilles | San Juan, PR | St Johns Antigua | St Lucia, Saint Lucia | St Thomas, VI | Tortola, British Virgin Islands | $699 Up To $75 Onboard Credit | | |
| Nov 21, 2026 | Emerald | Sakara | Caribbean - Eastern | San Juan | Miami | 7 Nights | Nassau, Bahamas | Miami, Florida | San Juan, Puerto Rico | $4,010 Up To $500 Onboard Credit | | |
| Dec 07, 2026 | Emerald | Sakara | Caribbean - Eastern | San Juan | St. Thomas | 6 Nights | $3,710 Up To $500 Onboard Credit | | Onboard Credit! |
| Jan 09, 2027 | Emerald | Sakara | Caribbean - Eastern | San Juan | St. Thomas | 7 Nights | Deshaies, Guadeloupe | Gustavia, Saint Barthélemy | San Juan, Puerto Rico | $4,210 Up To $500 Onboard Credit | | Onboard Credit! |
| Feb 13, 2027 | Emerald | Sakara | Caribbean - Eastern | San Juan | St. Thomas | 7 Nights | Deshaies, Guadeloupe | Gustavia, Saint Barthélemy | San Juan, Puerto Rico | $4,210 Up To $500 Onboard Credit | | |
| Mar 20, 2027 | Emerald | Sakara | Caribbean - Eastern | San Juan | St. Thomas | 7 Nights | Deshaies, Guadeloupe | Gustavia, Saint Barthélemy | San Juan, Puerto Rico | $4,210 Up To $500 Onboard Credit | | |
1 reviews | Jan 03, 2026 | Virgin Voyages | Valiant Lady | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Oranjestad, Aruba, Aruba | Philipsburg, Sint Maarten (Dutch part) | San Juan, Puerto Rico | Willemstad, Curacao, Curaçao | $2,470 Up To $500 Onboard Credit | | |
1 reviews | Jan 17, 2026 | Virgin Voyages | Valiant Lady | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Fort-de-France, Martinique, Martinique | Philipsburg, Sint Maarten (Dutch part) | San Juan, Puerto Rico | $2,666 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Feb 21, 2026 | Virgin Voyages | Valiant Lady | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bridgetown, Barbados, Barbados | Fort-de-France, Martinique, Martinique | Philipsburg, Sint Maarten (Dutch part) | Road Town, Tortola, BVI, Virgin Islands, British | San Juan, Puerto Rico | $2,600 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Mar 07, 2026 | Virgin Voyages | Valiant Lady | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Castries, St. Lucia, Saint Lucia | Fort-de-France, Martinique, Martinique | Road Town, Tortola, BVI, Virgin Islands, British | San Juan, Puerto Rico | $2,600 Up To $500 Onboard Credit | | |
15 reviews | Nov 03, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 13 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | Virgin Gorda | $4,749 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 03, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 6 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |