CruiseGrid
Showing 49–72 of 324 sailings
Booking links are affiliate — we may earn a commission at no extra cost to you.
  1. 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$1,049per guestas of 13 hours ago
    View sailing
  2. 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
    Philipsburg, St. Maarten · Charlotte Amalie · Basseterre, St. Kitts · Castries · Bridgetown
    From$2,219per guestas of 6 days ago
    View sailing
  3. 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$1,799per guestas of 12 hours ago
    View sailing
  4. 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$1,059per guestas of 13 hours ago
    View sailing
  5. 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$3,046per guestas of 12 hours ago
    View sailing
  6. 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$757per guestas of 13 hours ago
    View sailing
  7. 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$638per guestas of 13 hours ago
    View sailing
  8. 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), British Virgin Islands · Bridgetown · Castries · St. John's
    From$1,113per guestas of 11 hours ago
    View sailing
  9. 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$474per guestas of 12 hours ago
    View sailing
  10. 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$607per guestas of 13 hours ago
    View sailing
  11. CaribbeanNorwegian Cruise Line

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

    Norwegian Prima

    Departure
    Sun, Jan 3, 2027
    back Jan 10
    Length
    7 nights
    From San Juan
    Ports
    Tortola, British Virgin Islands · Oranjestad, Aruba · Willis Island (Cruising)
    From$1,459per guestas of 4 days ago
    View sailing
  12. 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$1,279per guestas of 12 hours ago
    View sailing
  13. 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$1,926per guestas of 12 hours ago
    View sailing
  14. 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$878per guestas of 13 hours ago
    View sailing
  15. 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$569per guestas of 13 hours ago
    View sailing
  16. 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$1,043per guestas of 11 hours ago
    View sailing
  17. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and St. Lucia

    Crown Princess

    Departure
    Sun, Jan 10, 2027
    back Jan 17
    Length
    7 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados
    From$679per guestas of 12 hours ago
    View sailing
  18. CaribbeanNorwegian Cruise Line

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

    Norwegian Prima

    Departure
    Sun, Jan 10, 2027
    back Jan 17
    Length
    7 nights
    From San Juan
    Ports
    Philipsburg, St. Maarten · Charlotte Amalie · Basseterre, St. Kitts · Castries · Bridgetown
    From$1,369per guestas of 6 days ago
    View sailing
  19. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Vision of the Seas

    Departure
    Sun, Jan 10, 2027
    back Jan 17
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · St. Croix · Philipsburg · St. Johns · Roseau
    From$549per guestas of 13 hours ago
    View sailing
  20. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer

    Crown Princess

    Departure
    Sun, Jan 10, 2027
    back Jan 24
    Length
    14 nights
    From San Juan
    Ports
    St. Thomas, Virgin Islands · St. Maarten · Antigua · St. Lucia · Barbados +6 more
    From$1,726per guestas of 12 hours ago
    View sailing
  21. CaribbeanVirgin Voyages

    7-night Caribbean cruise

    Valiant Lady

    Departure
    Sat, Jan 16, 2027
    back Jan 23
    Length
    7 nights
    From San Juan
    Ports
    Philipsburg · Bridgetown · Castries · Fort-de-France, Martinique
    From$1,113per guestas of 11 hours ago
    View sailing
  22. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Sat, Jan 16, 2027
    back Jan 23
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Philipsburg · St. Croix · St. Johns · Roseau
    From$548per guestas of 13 hours ago
    View sailing
  23. CaribbeanCelebrity Cruises

    Southern Caribbean

    Celebrity Constellation

    Departure
    Sat, Jan 16, 2027
    back Jan 23
    Length
    7 nights
    From San Juan
    Ports
    Charlotte Amalie · Basseterre · Roseau · Castries · Bridgetown
    From$1,091per guestas of 13 hours ago
    View sailing
  24. CaribbeanPrincess Cruises

    Southern Caribbean with Barbados and St. Lucia

    Crown Princess

    Departure
    Sun, Jan 17, 2027
    back Jan 24
    Length
    7 nights
    From San Juan
    Ports
    St. Maarten · Martinique · Grenada · St. Lucia · Barbados
    From$1,079per guestas of 12 hours ago
    View sailing