September 2025 Cruises to the Caribbean

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September 2025 Cruises to the Caribbean

We found you 145 cruises

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Icon of the Seas
Icon of the Seas (Rendering: Royal Caribbean)

7 Night
Eastern Caribbean & Perfect Day

20 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Reviews
  • Fare Insight
Icon of the Seas
Icon of the Seas (Rendering: Royal Caribbean)

7 Night
Western Caribbean & Perfect Day

20 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Reviews
  • Fare Insight
Wonder of the Seas
Wonder of the Seas in Labadee on March 6, 2022 (Photo: Aaron Saunders)

4 Night
Bahamas & Perfect Day Cruise

120 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight
MSC Seascape
MSC Seascape (Photo: MSC Cruises)

4 Night
Bahamas Cruise

191 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
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Sponsored

Score up to 80% off your 2nd Sailor

  • 80% off the second Sailor on all Mediterranean sailings
  • 70% off the second Sailor on all Caribbean sailings
  • Set sail from our homeports in Barcelona, Athens, Miami, or San Juan
  • Limited-Time Offer

Virgin Voyages

2 Night
Perfect Day Getaway Cruise

3,768 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

7 Night
Southern Caribbean Cruise

1,507 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

4 Night
Western Caribbean Cruise

1,332 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

5 Night
Western Caribbean Cruise

1,332 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

7 Night
Eastern Caribbean & Perfect Day

20 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Reviews
  • Fare Insight

7 Night
Southern Caribbean Cruise

1,507 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight
Cruise Critic Favorite

7 Night
Bahamas & Perfect Day Cruise

394 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight
Cruise Critic Favorite

6 Night
Western Caribbean Cruise

2,082 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

7 Night
7 Nt St. Maarten, St. Thomas & Bahamas

170 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

7 Night
Bahamas Cruise

841 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

4 Night
Bahamas Cruise

786 Reviews
Leaving:
Cruise Line:
No prices currently available for this sailing.
  • Itinerary
  • Ship
  • Reviews
  • Fare Insight

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