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Explore 399 cruise vacations
Showing Loading cruise vacations: Caribbean, July 2025 - October 2026
Departs San Juan, Puerto Rico
Showing 21 cruise vacations that match your search
Showing 21 cruise vacations that match your search

Saint (Isles) & Seas of the Caribbean
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Castries, St. Lucia
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor
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Sunny Miles of Tropical Isles
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Bridgetown, Barbados
- Castries, St. Lucia
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off 2nd Sailor
Insider cabins from
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Thanksgiving in the Lesser Antilles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off 2nd Sailor

San Juan to Barbados & the St. Isles
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Roseau, Dominica
- Bridgetown, Barbados
- San Juan, Puerto Rico
70% off 2nd Sailor

Nicky Jam x Virgin Voyages
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- Roseau, Dominica
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor

St. Lucia, St. Maarten, Barbados & More
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Roseau, Dominica
- Bridgetown, Barbados
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor

Valiant Caribbean Holidays
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off 2nd Sailor

Valiant New Year’s Ahoy!
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Bridgetown, Barbados
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
70% off 2nd Sailor

Aruban Sights & Antiguan Nights
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor

Virgin Island Views & Saint Isle Blues
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Kingstown, St. Vincent
- Basseterre, St. Kitts and Nevis
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
70% off 2nd Sailor

St. Kitts, Barbados, Martinique & More
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor

Barbados, Antigua, BVI & More
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor

Antigua & the St. Isles
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off 2nd Sailor

St. Lucia, Barbados & More
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Bridgetown, Barbados
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off 2nd Sailor

Valiant Valentine's Voyage
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. Croix, U.S. Virgin Islands
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off 2nd Sailor

Antigua, Martinique, & Barbados & More
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off 2nd Sailor

Quaint Castries to Elegant Antigua
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Fort-de-France, Martinique
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off 2nd Sailor

Sunsets in the Lesser Antilles
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off 2nd Sailor

Valiant's Haunted Halloween Soirée
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off 2nd Sailor