15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | 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 | $4,749 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130338__202301191125__.jpg.webp) | Nov 16, 2024 | Windstar | Star Pride | Caribbean - Eastern | 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 | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130342__202301191124__.jpg.webp) | Nov 23, 2024 | Windstar | Star Pride | Caribbean - Eastern | 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 | $4,449 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | 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) |
115 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/246.jpg.webp) | Mar 31, 2025 | Viking | Sea | Panama Canal | San Juan | Los Angeles (San Pedro) | 17 Nights | Cabo San Lucas, Mexico | Cartagena, Colombia | Colon, Panama | Leon (corinto), Nicaragua | Los Angeles | Puntarenas (puerto Caldera), Costa Rica | San Juan, Puerto Rico | Willemstad, Curacao | $5,999 | | |
![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/384__202302080932__.gif.webp) | Apr 12, 2025 | Virgin Voyages | Resilient Lady | Europe | San Juan | Barcelona | 14 Nights | Barcelona, Spain | Casablanca, Morocco | Palma de Mallorca, Spain | San Juan, Puerto Rico | Santa Cruz de Tenerife, Spain | Valencia, Spain | $3,024 Up To $500 Onboard Credit | | Onboard Credit! |
3 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/127756__202305101450__.jpg.webp) | Apr 13, 2025 | Norwegian | Viva | Transatlantic | San Juan | Lisbon | 13 Nights | Lisbon, Portugal | Philipsburg St Maarten, Netherland Antilles | Porto Grande, Cape Verde | Punta Cana (la Romana), Dominican Republic | San Juan, PR | Santa Cruz De Tenerife, Spain | $1,329 Shipboard Credit Per Stateroom Up To ($200) | | Shipboard Credit Per Stateroom Up To ($200) |
37 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/261.jpg.webp) | 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 $2,635You Save: $5,963 Up To $225 Onboard Credit | 69% | Onboard Credit! |
37 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/261.jpg.webp) | Apr 22, 2025 | Oceania | Sirena | Mediterranean | San Juan | Civitavecchia | 21 Nights | Alicante | Barcelona | Florence/pisa/tuscany (livorno) | Funchal (madeira) | Granada (motril) | Gustavia | Mahon (menorca) | Monte Carlo | Portofino | Rome (civitavecchia) | San Juan | Sanary-sur-mer | Sete | St. John's | Tangier | From: $12,198 $4,699You Save: $7,499 Up To $350 Onboard Credit | 61% | |
116 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/150511__202406181549__.jpg.webp) | Oct 12, 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. | $1,377 Up To $250 Onboard Credit | | Onboard Credit! |
116 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/150511__202406181549__.jpg.webp) | 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. | $1,377 Up To $250 Onboard Credit | | Onboard Credit! |
116 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/150511__202406181549__.jpg.webp) | 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. | $1,377 Up To $250 Onboard Credit | | Onboard Credit! |
116 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/150514__202406181549__.jpg.webp) | 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 | | |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | 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! |
47 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/164__201708090842__.jpg.webp) | 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 | $2,319 Up To $350 Onboard Credit | | Onboard Credit! |
116 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/150514__202406181549__.jpg.webp) | 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 | $1,348 Up To $250 Onboard Credit | | |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | 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 | | |
116 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/150515__202406181549__.jpg.webp) | Nov 16, 2025 | Princess | Grand Princess | Caribbean - Southern | San Juan | San Juan | 14 Nights | Bridgetown, Barbados | Dominica | Fort-De-France, Martinique | Grenada | Philipsburg, St. Maarten | San Juan, Puerto Rico | St. Croix, Virgin Islands | St. Johns, Antigua | St. Lucia | St. Thomas, Virgin Islands | $1,508 Up To $250 Onboard Credit | | Onboard Credit! |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | Nov 16, 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! |