CruiseGrid
Showing 1–24 of 28 sailings
Booking links are affiliate — we may earn a commission at no extra cost to you.
  1. 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$784per guestas of 15 hours ago
    View sailing
  2. 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$655per guestas of 15 hours ago
    View sailing
  3. 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$973per guestas of 1 day ago
    View sailing
  4. 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$825per guestas of 14 hours ago
    View sailing
  5. 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$639per guestas of 15 hours ago
    View sailing
  6. 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$1,839per guestas of 7 days ago
    View sailing
  7. 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$1,149per guestas of 14 hours ago
    View sailing
  8. 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$1,816per guestas of 14 hours ago
    View sailing
  9. 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$591per guestas of 15 hours ago
    View sailing
  10. 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$700per guestas of 15 hours ago
    View sailing
  11. 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 1 day ago
    View sailing
  12. 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$699per guestas of 14 hours ago
    View sailing
  13. 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
    Basseterre, St. Kitts · Castries · Bridgetown · Philipsburg, St. Maarten · Tortola, British Virgin Islands
    From$1,499per guestas of 7 days ago
    View sailing
  14. 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$601per guestas of 15 hours ago
    View sailing
  15. 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$1,596per guestas of 14 hours ago
    View sailing
  16. 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$560per guestas of 15 hours ago
    View sailing
  17. 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$1,043per guestas of 1 day ago
    View sailing
  18. 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$746per guestas of 15 hours ago
    View sailing
  19. CaribbeanNorwegian Cruise Line

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

    Norwegian Prima

    Departure
    Sun, Jan 17, 2027
    back Jan 24
    Length
    7 nights
    From San Juan
    Ports
    Kralendijk, Bonaire · Willis Island (Cruising) · Charlotte Amalie
    From$1,429per guestas of 7 days ago
    View sailing
  20. 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$929per guestas of 14 hours ago
    View sailing
  21. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Vision of the Seas

    Departure
    Sun, Jan 17, 2027
    back Jan 24
    Length
    7 nights
    From San Juan
    Ports
    Tortola · St. Johns · Fort De France · Kingstown · Basseterre
    From$629per guestas of 15 hours ago
    View sailing
  22. CaribbeanPrincess Cruises

    Southern Caribbean Adventurer

    Crown Princess

    Departure
    Sun, Jan 17, 2027
    back Jan 31
    Length
    14 nights
    From San Juan
    Ports
    St. Maarten · Martinique · Grenada · St. Lucia · Barbados +6 more
    From$1,696per guestas of 14 hours ago
    View sailing
  23. CaribbeanVirgin Voyages

    6-night Caribbean cruise

    Valiant Lady

    Departure
    Sat, Jan 23, 2027
    back Jan 29
    Length
    6 nights
    From San Juan
    Ports
    Road Town (Tortola), British Virgin Islands · Basseterre, St. Kitts · St. John's
    From$834per guestas of 1 day ago
    View sailing
  24. CaribbeanRoyal Caribbean International

    Southern Caribbean Cruise

    Rhapsody of the Seas

    Departure
    Sat, Jan 23, 2027
    back Jan 30
    Length
    7 nights
    From San Juan
    Ports
    Tortola · Philipsburg · St. Johns · Basseterre · St. Croix
    From$585per guestas of 15 hours ago
    View sailing