15 reviews | Nov 16, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 23, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Marigot, St. Martin | Pigeon Island | San Juan | St. George's | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 30, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | |
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 | | |
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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: $11,998 $3,599You Save: $8,399 Up To $500 Onboard Credit | 70% | |
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! |
122 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 | $799 Up To $75 Onboard Credit | | |
122 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! |
122 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 | | Onboard Credit! |
| Dec 07, 2026 | Emerald | Sakara | Caribbean - Eastern | San Juan | St. Thomas | 6 Nights | $3,710 Up To $500 Onboard Credit | | 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 | | 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 | | |
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 | | |
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 | 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) |
15 reviews | Nov 09, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $2,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 16, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Nov 23, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $2,599 Up To $300 Onboard Credit | | |
15 reviews | Nov 30, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | Bridgetown | 7 Nights | Bridgetown | Gustavia | Little Bay | Pigeon Island | Roseau | San Juan | St. George's | St. Thomas | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |