116 reviews | Oct 19, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bridgetown, Barbados | Dominica | Grenada | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Johns, Antigua | St. Kitts | St. Lucia | St. Thomas, Virgin Islands | Tortola, B.V.I. | $1,277 Up To $250 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
116 reviews | Oct 19, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Johns, Antigua | St. Lucia | St. Thomas, Virgin Islands | $638 Up To $150 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
58 reviews | Oct 26, 2025 | Royal Caribbean | Rhapsody of the Seas | Caribbean - Southern | San Juan | San Juan | 7 Nights | Bridgetown - Barbados | Charlotte Amalie - St. Thomas | Philipsburg - St. Maarten | San Juan - Puerto Rico | St. Croix - U.s.v.i. | St. Johns - Antigua | $548 Up To $150 Onboard Credit | | *** | View Itinerary | Get FREE Quote |
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 | $2,699 Up To $300 Onboard Credit | | Suite! | View Itinerary | Get FREE Quote |
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116 reviews | Oct 26, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bridgetown, Barbados | Dominica | Grenada | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Johns, Antigua | St. Kitts | St. Lucia | St. Thomas, Virgin Islands | Tortola, B.V.I. | $1,277 Up To $250 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
116 reviews | Oct 26, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Dominica | Grenada | San Juan, Puerto Rico | St. Kitts | Tortola, B.V.I. | $638 Up To $150 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
115 reviews | Oct 29, 2025 | 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) | $3,599 | | | View Itinerary | Get FREE Quote |
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 | $2,699 Up To $300 Onboard Credit | | Suite! | View Itinerary | Get FREE Quote |
116 reviews | Nov 02, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Johns, Antigua | St. Lucia | St. Thomas, Virgin Islands | $638 Up To $150 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
116 reviews | Nov 02, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bridgetown, Barbados | Fort-De-France, Martinique | Grenada | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Croix, Virgin Islands | St. Johns, Antigua | St. Kitts | St. Thomas, Virgin Islands | St. Vincent | $1,448 Up To $250 Onboard Credit | | | View Itinerary | Get FREE Quote |
15 reviews | Nov 02, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 14 Nights | Basseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $4,299 Up To $500 Onboard Credit | | Suite! | View Itinerary | Get FREE Quote |
82 reviews | Nov 08, 2025 | Royal Caribbean | Jewel of the Seas | Caribbean - Southern | San Juan | San Juan | 7 Nights | Bridgetown - Barbados | Charlotte Amalie - St. Thomas | Philipsburg - St. Maarten | Roseau - Dominica | San Juan - Puerto Rico | St. Croix - U.s.v.i. | $709 Up To $150 Onboard Credit | | *** | View Itinerary | Get FREE Quote |
48 reviews | Nov 08, 2025 | Azamara | Quest | Caribbean - Eastern | San Juan | San Juan | 14 Nights | BASSETERRE | BEEF ISLAND, TORTOLA | BRIDGETOWN | CASTRIES | CHARLESTOWN | PHILIPSBURG | PORT ELIZABETH, BEQUIA | ROSEAU | SAN JUAN, PUERTO RICO | SCARBOROUGH, TOBAGO | ST. JOHN'S, ANTIGUA | ST. PIERRE | VIRGIN GORDA | $2,260 Up To $350 Onboard Credit | | | View Itinerary | Get FREE Quote |
116 reviews | Nov 09, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Dominica | Grenada | San Juan, Puerto Rico | St. Kitts | Tortola, B.V.I. | $638 Up To $150 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
116 reviews | Nov 09, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bridgetown, Barbados | Fort-De-France, Martinique | Grenada | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Croix, Virgin Islands | St. Johns, Antigua | St. Kitts | St. Thomas, Virgin Islands | St. Vincent | $1,327 Up To $250 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
15 reviews | Nov 09, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 14 Nights | Basseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $4,299 Up To $500 Onboard Credit | | Suite! | View Itinerary | Get FREE Quote |
82 reviews | Nov 15, 2025 | Royal Caribbean | Jewel of the Seas | Caribbean - Southern | San Juan | San Juan | 7 Nights | Bridgetown - Barbados | Charlotte Amalie - St. Thomas | Philipsburg - St. Maarten | Roseau - Dominica | San Juan - Puerto Rico | St. Croix - U.s.v.i. | $709 Up To $150 Onboard Credit | | *** | View Itinerary | Get FREE Quote |
1 reviews | Nov 15, 2025 | Virgin Voyages | Valiant Lady | Caribbean - Southern | 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 | $2,438 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
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 | | | View Itinerary | Get FREE Quote |
116 reviews | Nov 16, 2025 | Princess | Grand Princess | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bridgetown, Barbados | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Johns, Antigua | St. Lucia | St. Thomas, Virgin Islands | $688 Shipboard Credit Per Stateroom ($50) | | Shipboard Credit Per Stateroom ($50) | View Itinerary | Get FREE Quote |