113 reviews | Jan 28, 2026 | Viking | Sea | Caribbean | San Juan | San Juan | 10 Nights | Antigua (st. John's), Antigua | Bridgetown, Barbados | Castries, St Lucia | Philipsburg | Roseau, Dominica | San Juan, Puerto Rico | St. Kitts (basseterre), St Kitts | St. Thomas (charlotte Amalie) | Tortola (road Town) | $3,799 | | |
113 reviews | Feb 07, 2026 | Viking | Sea | Caribbean | San Juan | San Juan | 10 Nights | Antigua (st. John's), Antigua | Bridgetown, Barbados | Castries, St Lucia | Philipsburg | Roseau, Dominica | San Juan, Puerto Rico | St. Kitts (basseterre), St Kitts | St. Thomas (charlotte Amalie) | Tortola (road Town) | $3,799 | | Balcony! |
113 reviews | Feb 17, 2026 | Viking | Sea | Caribbean | San Juan | San Juan | 10 Nights | Antigua (st. John's), Antigua | Bridgetown, Barbados | Castries, St Lucia | Philipsburg | Roseau, Dominica | San Juan, Puerto Rico | St. Kitts (basseterre), St Kitts | St. Thomas (charlotte Amalie) | Tortola (road Town) | $3,799 | | Balcony! |
113 reviews | Feb 27, 2026 | Viking | Sea | Caribbean | San Juan | San Juan | 10 Nights | Antigua (st. John's), Antigua | Bridgetown, Barbados | Castries, St Lucia | Philipsburg | Roseau, Dominica | San Juan, Puerto Rico | St. Kitts (basseterre), St Kitts | St. Thomas (charlotte Amalie) | Tortola (road Town) | $3,799 | | Balcony! |
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113 reviews | Mar 09, 2026 | Viking | Sea | Caribbean | San Juan | San Juan | 10 Nights | Antigua (st. John's), Antigua | Bridgetown, Barbados | Castries, St Lucia | Philipsburg | Roseau, Dominica | San Juan, Puerto Rico | St. Kitts (basseterre), St Kitts | St. Thomas (charlotte Amalie) | Tortola (road Town) | $3,799 | | Balcony! |
113 reviews | Mar 19, 2026 | Viking | Sea | Caribbean | San Juan | San Juan | 10 Nights | Antigua (st. John's), Antigua | Bridgetown, Barbados | Castries, St Lucia | Philipsburg | Roseau, Dominica | San Juan, Puerto Rico | St. Kitts (basseterre), St Kitts | St. Thomas (charlotte Amalie) | Tortola (road Town) | $3,799 | | |
| Dec 06, 2024 | Virgin Voyages | Resilient Lady | Caribbean | San Juan | San Juan | 8 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Fort-de-France, Martinique, Martinique | Philipsburg, Sint Maarten (Dutch part) | Road Town, Tortola, BVI, Virgin Islands, British | San Juan, Puerto Rico | $2,578 Up To $500 Onboard Credit | | Onboard Credit! |
| Dec 21, 2024 | Virgin Voyages | Resilient Lady | Caribbean | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Fort-de-France, Martinique, Martinique | Philipsburg, Sint Maarten (Dutch part) | San Juan, Puerto Rico | $2,882 Up To $500 Onboard Credit | | |
| Mar 01, 2025 | Virgin Voyages | Resilient Lady | Caribbean | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Fort-de-France, Martinique, Martinique | Philipsburg, Sint Maarten (Dutch part) | San Juan, Puerto Rico | $2,746 Up To $300 Onboard Credit | | Onboard Credit! |
1 reviews | Dec 20, 2025 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 7 Nights | Miami, Florida, USA | Puerto Plata, Dominican Republic | San Juan, Puerto Rico | The Beach Club at Bimini, Bahamas | $2,926 Up To $500 Onboard Credit | | Onboard Credit! |
15 reviews | Nov 09, 2024 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda / Prickly Pear | $4,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2024 | Windstar | Star Pride | Caribbean | San Juan | Oranjestad | 14 Nights | Bridgetown | Gustavia | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Oct 26, 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 | $2,899 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 02, 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 | $2,899 Up To $300 Onboard Credit | | |
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 | $2,899 Up To $300 Onboard Credit | | |
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 | $2,899 Up To $300 Onboard Credit | | Suite! |
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 | 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 |
37 reviews | Apr 22, 2025 | Oceania | Sirena | Caribbean - Eastern | San Juan | Barcelona | 14 Nights | Alicante | Barcelona | Funchal (madeira) | Granada (motril) | Gustavia | San Juan | St. John's | Tangier | From: $8,598 $3,099You Save: $5,499 Up To $275 Onboard Credit | 63% | |
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 | $4,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |