CruiseGrid
Showing 49–72 of 329 sailings
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  1. CaribbeanSilversea Cruises

    San Juan to San Juan

    Silver Shadow

    Departure
    Sun, Dec 20, 2026
    back Dec 27
    Length
    7 nights
    From San Juan
    Ports
    Jost Van Dyke (British Virgin Islands) · Little Bay, Montserrat · Castries (St. Lucia) · Fort-de-France · Sopers Hole
    From$2,870per guestas of 2 days ago
    View sailing
  2. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Vision of the Seas

    Departure
    Sun, Dec 20, 2026
    back Dec 27
    Length
    7 nights
    From San Juan
    Ports
    Tortola · St. Johns · Roseau · St. Croix · Basseterre
    From$642per guestas of 19 minutes ago
    View sailing
  3. CaribbeanNorwegian Cruise Line

    7-Day Caribbean Round-Trip San Juan: St. Thomas & Tortola

    Norwegian Prima

    Departure
    Sun, Dec 20, 2026
    back Dec 27
    Length
    7 nights
    From San Juan
    Ports
    Oranjestad, Aruba · Willis Island (Cruising) · Charlotte Amalie
    From$1,459per guestas of 1 hour ago
    View sailing
  4. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Constellation

    Departure
    Sat, Dec 26, 2026
    back Jan 2
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Philipsburg · St. Johns · Castries · Bridgetown
    From$1,129per guestas of 11 minutes ago
    View sailing
  5. CaribbeanRoyal Caribbean International

    Southern Caribbean Holiday

    Rhapsody of the Seas

    Departure
    Sat, Dec 26, 2026
    back Jan 2
    Length
    7 nights
    From San Juan
    Ports
    Tortola · Philipsburg · St. Johns · Basseterre · Charlotte Amalie
    From$821per guestas of 16 minutes ago
    View sailing
  6. CaribbeanVirgin Voyages

    7-night Caribbean cruise

    Valiant Lady

    Departure
    Sat, Dec 26, 2026
    back Jan 2
    Length
    7 nights
    From San Juan
    Ports
    Philipsburg · Fort-de-France, Martinique · Bridgetown · Castries
    From$1,953per guestas of 23 hours ago
    View sailing
  7. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Vision of the Seas

    Departure
    Sun, Dec 27, 2026
    back Jan 3
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Croix · Philipsburg · St. Johns · Roseau
    From$848per guestas of 20 minutes ago
    View sailing
  8. CaribbeanNorwegian Cruise Line

    7-day Caribbean Round-trip San Juan: Barbados & St. Thomas

    Norwegian Prima

    Departure
    Sun, Dec 27, 2026
    back Jan 3
    Length
    7 nights
    From San Juan
    Ports
    Basseterre, St. Kitts · Castries · Bridgetown · Philipsburg, St. Maarten · Tortola, British Virgin Islands
    From$2,589per guestas of 1 hour ago
    View sailing
  9. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and St. Lucia Holiday

    Crown Princess

    Departure
    Sun, Dec 27, 2026
    back Jan 3
    Length
    7 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados
    From$2,099per guestas of 1 day ago
    View sailing
  10. CaribbeanSilversea Cruises

    San Juan to San Juan

    Silver Shadow

    Departure
    Sun, Dec 27, 2026
    back Jan 3
    Length
    7 nights
    From San Juan
    Ports
    St John · St. Kitts (Basseterre) · Les Saintes · Bequia · St. Thomas
    From$4,640per guestas of 2 days ago
    View sailing
  11. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer

    Crown Princess

    Departure
    Sun, Dec 27, 2026
    back Jan 10
    Length
    14 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados +6 more
    From$3,246per guestas of 1 day ago
    View sailing
  12. CaribbeanSilversea Cruises

    San Juan to Miami, FL

    Silver Nova

    Departure
    Tue, Dec 29, 2026
    back Jan 6
    Length
    8 nights
    From San Juan
    Ports
    St John · Charlestown (Nevis) · Roseau · St. John's · Jost Van Dyke (British Virgin Islands)
    From$4,480per guestas of 2 days ago
    View sailing
  13. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Sat, Jan 2, 2027
    back Jan 9
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Philipsburg · St. Croix · St. Johns · Roseau
    From$652per guestas of 20 minutes ago
    View sailing
  14. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Constellation

    Departure
    Sat, Jan 2, 2027
    back Jan 9
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Basseterre · Roseau · Castries · Bridgetown
    From$749per guestas of 11 minutes ago
    View sailing
  15. CaribbeanVirgin Voyages

    7-night Caribbean cruise

    Valiant Lady

    Departure
    Sat, Jan 2, 2027
    back Jan 9
    Length
    7 nights
    From San Juan
    Ports
    Road Town, Tortola · Bridgetown · Castries · St. John's
    From$973per guestas of 23 hours ago
    View sailing
  16. CaribbeanPrincess Cruises

    Eastern Caribbean with St. Kitts

    Crown Princess

    Departure
    Sun, Jan 3, 2027
    back Jan 8
    Length
    5 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Kitts · Dominica · Grenada
    From$847per guestas of 1 day ago
    View sailing
  17. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Vision of the Seas

    Departure
    Sun, Jan 3, 2027
    back Jan 10
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Johns · Roseau · St. Croix · Basseterre
    From$589per guestas of 18 minutes ago
    View sailing
  18. CaribbeanSilversea Cruises

    San Juan to San Juan

    Silver Shadow

    Departure
    Sun, Jan 3, 2027
    back Jan 10
    Length
    7 nights
    From San Juan
    Ports
    St John · Gustavia, St. Barthelemy · St. John's · Little Bay, Montserrat · St. Kitts (Basseterre) +1 more
    From$3,420per guestas of 2 days ago
    View sailing
  19. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and St. Kitts

    Crown Princess

    Departure
    Sun, Jan 3, 2027
    back Jan 10
    Length
    7 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Kitts · Dominica · Grenada · Barbados
    From$1,179per guestas of 1 day ago
    View sailing
  20. CaribbeanNorwegian Cruise Line

    7-Day Caribbean Round-Trip San Juan: St. Thomas & Tortola

    Norwegian Prima

    Departure
    Sun, Jan 3, 2027
    back Jan 10
    Length
    7 nights
    From San Juan
    Ports
    Oranjestad, Aruba · Willis Island (Cruising) · Charlotte Amalie
    From$1,889per guestas of 1 hour ago
    View sailing
  21. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer

    Crown Princess

    Departure
    Sun, Jan 3, 2027
    back Jan 17
    Length
    14 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Kitts · Dominica · Grenada · Barbados +6 more
    From$1,846per guestas of 1 day ago
    View sailing
  22. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Constellation

    Departure
    Sat, Jan 9, 2027
    back Jan 16
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Philipsburg · St. Johns · Castries · St. George's
    From$858per guestas of 10 minutes ago
    View sailing
  23. CaribbeanVirgin Voyages

    7-night Caribbean cruise

    Valiant Lady

    Departure
    Sat, Jan 9, 2027
    back Jan 16
    Length
    7 nights
    From San Juan
    Ports
    Oranjestad, Aruba · Willemstad · Fort-de-France, Martinique
    From$973per guestas of 23 hours ago
    View sailing
  24. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Sat, Jan 9, 2027
    back Jan 16
    Length
    7 nights
    From San Juan
    Ports
    St. Croix · Philipsburg · St. Johns · Fort De France · Basseterre
    From$515per guestas of 19 minutes ago
    View sailing