Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 363 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 523 departures starting between May 2024 and April 2027.
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7 Days
86 Days
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$1,600pp
$37,350pp
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363 Cruises (523 Cruise Departures)
Cruise

8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 13 December 2024
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,192
SUITE
$7,529
From 6,192
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 21 March 2025
Countries Visited: USA, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
$10,955
BALCONY
$13,757
SUITE
$15,242
Save 4,795
From 10,955
Cruise

16 Days (15 Nights) New York to Miami
Cruise Line: Regent Seven Seas
Departure: 23 October 2024
Countries Visited: USA, Bermuda, Saint Barthelemy, Saint Lucia (+5 more), Barbados, Grenada, Bonaire, Curacao, Aruba
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$12,928
SUITE
$14,094
Save 9,312
From 12,928
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 08 April 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Grenada (+3 more), Barbados, Dominica, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,972
SUITE
$10,734
Save 2,058
From 6,972
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 09 March 2026
Countries Visited: USA, Aruba, Curacao, Grenada (+3 more), Saint Vincent, Martinique, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,479
SUITE
$12,013
Save 2,061
From 7,479
Cruise

10 Days (9 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Departure: 22 November 2025
Countries Visited: Barbados, Saint Lucia, Saint Vincent, Bonaire (+3 more), Curacao, Aruba, Colombia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,009
BALCONY
$9,504
SUITE
$14,058
From 9,009
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 22 December 2025
Countries Visited: USA, Turks and Caicos Islands, Virgin Islands, Saint Kitts and Nevis (+5 more), Dominica, Martinique, Saint Vincent, Antigua and Barbuda, Puerto Rico
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$14,058
BALCONY
$15,345
SUITE
$21,582
From 14,058
Cruise

10 Days (9 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Dominican Republic, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$9,935
SUITE
$12,118
From 9,935
Cruise

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+4 more), Martinique, Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,056
SUITE
$9,853
From 5,056
Cruise

14 Days (13 Nights) Fort Lauderdale to Lima
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 06 January 2026
Countries Visited: USA, Mexico, Costa Rica, Panama (+2 more), Ecuador, Peru
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$15,493
BALCONY
$16,780
SUITE
$32,026
From 15,493
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+1 more), USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,401
SUITE
$5,371
From 4,401
Cruise

16 Days (15 Nights) Oranjestad to Bridgetown
Cruise Line: Oceania Cruises
Departure: 27 November 2024
Countries Visited: Aruba, Curacao, Jamaica, Dominican Republic (+10 more), Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Guadeloupe, Martinique, Saint Lucia, Grenada, Barbados
Cabin Upgrade Offer
INSIDE
$4,828
OCEANVIEW
$4,828
BALCONY
$5,897
SUITE
$8,332
From 4,828
Cruise

15 Days (14 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2025
Countries Visited: USA, Virgin Islands, Dominica, Guadeloupe (+7 more), Saint Martin, Puerto Rico, Aruba, Curacao, Bonaire, Trinidad and Tobago, Barbados
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$9,702
SUITE
$11,880
From 9,702
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departures: Feb 2026 to Apr 2026
Countries Visited: USA, Puerto Rico, Saint Kitts and Nevis, Saint Lucia (+2 more), Dominica, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,190
SUITE
$9,942
Save 2,052
From 6,190
Cruise

8 Days (7 Nights) Bridgetown to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 February 2025
Countries Visited: Barbados, Saint Lucia, Martinique, Saint Vincent (+3 more), Trinidad and Tobago, Grenada, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,782
SUITE
$6,692
From 5,782
New ReleaseCruise

14 Days (13 Nights) Miami to Saint Thomas
Cruise Line: Emerald Cruises
Departure: 30 November 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands, Puerto Rico (+4 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,712
BALCONY
-
SUITE
$10,430
Save 9,078
From 7,712
New ReleaseCruise

8 Days (7 Nights) Saint Thomas to Saint Thomas
Cruise Line: Emerald Cruises
Departures: Dec 2026 to Mar 2027
Countries Visited: Virgin Islands, Saint Martin, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,440
BALCONY
-
SUITE
$6,979
Save 3,559
From 5,440
Cruise

15 Days (14 Nights) Philipsburg to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Feb 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$11,794
SUITE
$20,462
From 11,794
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 28 January 2025
Countries Visited: USA, Mexico, Belize
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,663
SUITE
$5,692
From 4,663
Cruise

22 Days (21 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 20 December 2025
Countries Visited: USA, Aruba, Bonaire, Curacao (+8 more), Grenada, Saint Lucia, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$17,322
SUITE
$20,570
Save 10,548
From 17,322
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 24 November 2024
Countries Visited: USA, Aruba, Curacao, Bonaire (+4 more), Grenada, Saint Lucia, Saint Barthelemy, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,873
SUITE
$11,913
Save 3,447
From 10,873
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 01 December 2025
Countries Visited: USA, Puerto Rico, Saint Barthelemy, Sint Maarten (+3 more), Virgin Islands, Dominican Republic, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,437
SUITE
$9,912
Save 6,123
From 8,437
Cruise

12 Days (11 Nights) Miami to San Juan
Cruise Line: Regent Seven Seas
Departure: 23 December 2024
Countries Visited: USA, Jamaica, Aruba, Curacao (+4 more), Bonaire, Virgin Islands, Sint Maarten, Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,436
BALCONY
$11,683
SUITE
$13,168
Save 3,874
From 8,436
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 22 December 2025
Countries Visited: USA, Dominican Republic, Virgin Islands, Saint Martin (+1 more), Puerto Rico
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,816
SUITE
$8,286
From 6,816
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 22 December 2025
Countries Visited: USA, Saint Kitts and Nevis, Antigua and Barbuda, Martinique (+4 more), Barbados, Grenada, Saint Lucia, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,765
SUITE
$11,399
Save 6,135
From 9,765
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 14 March 2026
Countries Visited: USA, Mexico, Guatemala, Belize (+3 more), Honduras, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,956
SUITE
$12,877
Save 6,294
From 10,956
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 14 January 2025
Countries Visited: USA, Virgin Islands, Saint Barthelemy, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,608
SUITE
$5,371
From 4,608
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Jan 2026 to Feb 2026
Countries Visited: USA, Virgin Islands, Guadeloupe, Saint Lucia (+1 more), Montserrat
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,168
SUITE
$8,752
From 7,168
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 24 January 2025
Countries Visited: USA, Saint Barthelemy, Guadeloupe, Saint Vincent (+3 more), Saint Lucia, Antigua and Barbuda, Virgin Islands
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$9,172
SUITE
$11,192
From 9,172
New ReleaseCruise

7 Days (6 Nights) Saint Thomas to San Juan
Cruise Line: Emerald Cruises
Departure: 03 January 2027
Countries Visited: Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy (+1 more), Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$4,599
BALCONY
-
SUITE
$5,777
Save 3,546
From 4,599
Results: 61-90 of 363

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Caribbean & Bahamas Cruises