CruiseGrid
Showing 169–192 of 346 sailings
Booking links are affiliate — we may earn a commission at no extra cost to you.
  1. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Summit

    Departure
    Sun, Dec 5, 2027
    back Dec 12
    Length
    7 nights
    From San Juan
    Ports
    Roseau · Bridgetown · Castries · St. Johns · Charlotte Amalie
    From$789per guestas of 5 hours ago
    View sailing
  2. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer

    Emerald Princess

    Departure
    Sun, Dec 5, 2027
    back Dec 19
    Length
    14 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados +6 more
    From$1,428per guestas of 5 hours ago
    View sailing
  3. CaribbeanDisney Cruise Line

    5-Night Very Merrytime Eastern Caribbean Cruise from San Juan ending in Fort Lauderdale

    Disney Fantasy

    Departure
    Fri, Dec 10, 2027
    back Dec 15
    Length
    5 nights
    From San Juan
    From$1,220per guestas of 2 hours ago
    View sailing
  4. CaribbeanVirgin Voyages

    7-night Caribbean cruise

    Scarlet Lady

    Departure
    Sat, Dec 11, 2027
    back Dec 18
    Length
    7 nights
    From San Juan
    Ports
    Philipsburg · St. John's · Castries
    From$833per guestas of 3 hours ago
    View sailing
  5. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Sat, Dec 11, 2027
    back Dec 18
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Croix · Philipsburg · Castries · Bridgetown
    From$730per guestas of 5 hours ago
    View sailing
  6. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Vision of the Seas

    Departure
    Sun, Dec 12, 2027
    back Dec 19
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Philipsburg · Willemstad · Oranjestad
    From$723per guestas of 5 hours ago
    View sailing
  7. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and Tortola

    Emerald Princess

    Departure
    Sun, Dec 12, 2027
    back Dec 19
    Length
    7 nights
    From San Juan
    Ports
    Tortola, British Virgin Islands · St. Kitts · Martinique · Dominica · Barbados
    From$774per guestas of 4 hours ago
    View sailing
  8. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Summit

    Departure
    Sun, Dec 12, 2027
    back Dec 19
    Length
    7 nights
    From San Juan
    Ports
    Kingstown · Bridgetown · Fort De France · St. Johns · Charlotte Amalie
    From$810per guestas of 5 hours ago
    View sailing
  9. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer Holiday

    Emerald Princess

    Departure
    Sun, Dec 12, 2027
    back Dec 26
    Length
    14 nights
    From San Juan
    Ports
    Tortola, British Virgin Islands · St. Kitts · Martinique · Dominica · Barbados +6 more
    From$1,438per guestas of 4 hours ago
    View sailing
  10. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Sat, Dec 18, 2027
    back Dec 24
    Length
    6 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Croix · Basseterre · St. Johns
    From$768per guestas of 5 hours ago
    View sailing
  11. CaribbeanNorwegian Cruise Line

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

    Norwegian Prima

    Departure
    Sat, Dec 18, 2027
    back Dec 25
    Length
    7 nights
    From San Juan
    Ports
    Tortola, British Virgin Islands · Bridgetown · Charlotte Amalie · Basseterre, St. Kitts · Castries
    From$1,809per guestas of 6 hours ago
    View sailing
  12. CaribbeanVirgin Voyages

    8-night Caribbean cruise

    Scarlet Lady

    Departure
    Sat, Dec 18, 2027
    back Dec 26
    Length
    8 nights
    From San Juan
    Ports
    Philipsburg · St. John's · Oranjestad, Aruba
    From$1,112per guestas of 3 hours ago
    View sailing
  13. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Summit

    Departure
    Sun, Dec 19, 2027
    back Dec 26
    Length
    7 nights
    From San Juan
    Ports
    Roseau · Bridgetown · Castries · St. Johns · Charlotte Amalie
    From$914per guestas of 5 hours ago
    View sailing
  14. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and St. Lucia Holiday

    Emerald Princess

    Departure
    Sun, Dec 19, 2027
    back Dec 26
    Length
    7 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados
    From$694per guestas of 4 hours ago
    View sailing
  15. CaribbeanRoyal Caribbean International

    Southern Caribbean Holiday Cruise

    Vision of the Seas

    Departure
    Sun, Dec 19, 2027
    back Dec 27
    Length
    8 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Johns · Roseau · St. George's · Bridgetown +1 more
    From$1,129per guestas of 5 hours ago
    View sailing
  16. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer Holiday

    Emerald Princess

    Departure
    Sun, Dec 19, 2027
    back Jan 2
    Length
    14 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados +6 more
    From$1,618per guestas of 4 hours ago
    View sailing
  17. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Fri, Dec 24, 2027
    back Dec 31
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Philipsburg · St. Johns · St. Croix · Basseterre
    From$1,079per guestas of 5 hours ago
    View sailing
  18. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and Tortola Holiday

    Emerald Princess

    Departure
    Sun, Dec 26, 2027
    back Jan 2
    Length
    7 nights
    From San Juan
    Ports
    Tortola, British Virgin Islands · St. Kitts · Dominica · Grenada · Barbados
    From$954per guestas of 4 hours ago
    View sailing
  19. CaribbeanVirgin Voyages

    7-night Caribbean cruise

    Scarlet Lady

    Departure
    Sun, Dec 26, 2027
    back Jan 2
    Length
    7 nights
    From San Juan
    Ports
    Philipsburg · Bridgetown · Fort-de-France, Martinique · St. John's
    From$1,673per guestas of 3 hours ago
    View sailing
  20. CaribbeanCelebrity Cruises

    Southern Caribbean Holiday

    Celebrity Summit

    Departure
    Sun, Dec 26, 2027
    back Jan 2
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Bridgetown · Castries · St. Johns · Philipsburg
    From$1,260per guestas of 5 hours ago
    View sailing
  21. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer Holiday

    Emerald Princess

    Departure
    Sun, Dec 26, 2027
    back Jan 9
    Length
    14 nights
    From San Juan
    Ports
    Tortola, British Virgin Islands · St. Kitts · Dominica · Grenada · Barbados +6 more
    From$1,688per guestas of 4 hours ago
    View sailing
  22. CaribbeanRoyal Caribbean International

    Southern Caribbean Holiday Cruise

    Vision of the Seas

    Departure
    Mon, Dec 27, 2027
    back Jan 3
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Kralendijk · Willemstad · Oranjestad
    From$1,180per guestas of 5 hours ago
    View sailing
  23. CaribbeanRoyal Caribbean International

    Southern Caribbean Holiday Cruise

    Rhapsody of the Seas

    Departure
    Fri, Dec 31, 2027
    back Jan 8
    Length
    8 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Croix · Basseterre · Castries · St. Johns +1 more
    From$1,308per guestas of 5 hours ago
    View sailing
  24. CaribbeanCelebrity Cruises

    San Juan to Ft. Lauderdale

    Celebrity Summit

    Departure
    Sun, Jan 2, 2028
    back Jan 6
    Length
    4 nights
    From San Juan
    Ports
    Philipsburg
    From$541per guestas of 5 hours ago
    View sailing