Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 537 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 700 departures starting between January 2026 and April 2028.
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6 Days
91 Days
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$600pp
$133,998pp
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537 Cruises (700 Cruise Departures)
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Silversea
Departures: Nov 2027 to Dec 2027
Visit: USA, Bahamas, Turks and Caicos Islands
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$2,880
Balcony
$3,600
Suite
$4,140
From
US$2,880
Save 720
Per Person
View Trip
New ReleaseCruise
 (3)

12 Days (11 Nights) Bridgetown to Panama City
Cruise Line: Emerald Cruises
Departure: 13 January 2028
Visit: Barbados, Saint Vincent, Bonaire, Curacao, Aruba, Colombia, Panama
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$10,249
Balcony
-
Suite
$12,917
From
US$10,249
Save 12,741
Per Person
View Trip
Cruise

12 Days (11 Nights) Galveston to Galveston
Cruise Line: Regent Seven Seas
Departure: 30 November 2026
Visit: USA, Cayman Islands, Honduras, Belize, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,390
Suite
$7,615
From
US$6,390
Save 12,608
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 07 March 2027
Visit: Puerto Rico, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Turks and Caicos Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,720
Suite
$5,440
From
US$4,720
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 13 November 2027
Visit: Puerto Rico, Virgin Islands, Dominican Republic, USA, Bahamas
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 27 January 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Kitts and Nevis
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,709
Suite
$5,358
From
US$3,709
Save 3,889
Per Person
View Trip
Cruise

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 01 March 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands (+5 more), Saint Kitts and Nevis, Antigua and Barbuda, Mexico, Honduras, Belize
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,110
Suite
$11,311
From
US$8,110
Save 8,488
Per Person
View Trip
Cruise
 (1)

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 28 November 2027
Visit: USA, Aruba, Curacao, Bonaire (+4 more), Grenada, Saint Lucia, Guadeloupe, Saint Martin
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$3,329
Oceanview
$3,620
Balcony
$5,463
Suite
$7,500
From
US$3,329
Save 3,469
Per Person
View Trip
Cruise
 (8)

15 Days (14 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Departure: 30 November 2027
Visit: USA, Virgin Islands, Saint Martin, Martinique (+5 more), Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$3,523
Oceanview
$4,348
Balcony
$5,502
Suite
$8,082
From
US$3,523
Save 76
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 February 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,720
Suite
$5,440
From
US$4,720
Per Person
View Trip
Cruise

11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Regent Seven Seas
Departure: 14 February 2028
Visit: Barbados, Grenada, Saint Vincent, Saint Lucia (+5 more), Martinique, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,896
Suite
$6,925
From
US$5,896
Save 12,102
Per Person
View Trip
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2026
Visit: USA, Mexico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,410
Suite
$6,600
From
US$6,410
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 January 2027
Visit: USA, Jamaica, Guatemala, Honduras, Belize
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,935
Suite
$5,565
From
US$4,935
Per Person
View Trip
Cruise
 (3)

11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Departure: 18 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+4 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$2,382
Oceanview
$3,042
Balcony
$3,692
Suite
$5,719
From
US$2,382
Save 57
Per Person
View Trip
Cruise
 (8)

8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Departure: 07 December 2027
Visit: Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico, USA
Azamara Always Included
Inside
$1,809
Oceanview
$2,178
Balcony
$2,750
Suite
$4,040
From
US$1,809
Per Person
View Trip
Cruise

11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Silversea
Departure: 06 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+7 more), Montserrat, Guadeloupe, Dominica, Martinique, Saint Lucia, Grenada, Barbados
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,960
Balcony
$5,920
Suite
$8,900
From
US$4,960
Save 1,240
Per Person
View Trip
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 February 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+6 more), Anguilla, USA, Dominican Republic, Dominica, Barbados, Guadeloupe
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$10,910
From
US$10,910
Per Person
View Trip
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 19 December 2026
Visit: USA, Virgin Islands, Dominica, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,466
Suite
$8,495
From
US$7,466
Save 13,132
Per Person
View Trip
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 04 March 2028
Visit: USA, Mexico, Belize, Honduras, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,293
Suite
$6,734
From
US$6,293
Save 12,505
Per Person
View Trip
Cruise
 (3)

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 26 January 2028
Visit: USA, Aruba, Curacao, Bonaire (+4 more), Grenada, Saint Lucia, Saint Barthelemy, Virgin Islands
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$3,714
Oceanview
$4,732
Balcony
$5,557
Suite
$7,788
From
US$3,714
Save 3,884
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 December 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Saint Martin, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,655
Suite
$4,120
From
US$3,655
Per Person
View Trip
New ReleaseCruise
 (3)

14 Days (13 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Departure: 03 January 2027
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+5 more), Saint Barthelemy, Saint Martin, Anguilla, Virgin Islands, Saint Kitts and Nevis
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$9,321
From
US$9,321
Save 11,959
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 10 March 2026
Visit: USA, Mexico, Honduras, Belize
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
$1,650
Oceanview
$1,837
Balcony
-
Suite
-
From
US$1,650
Save 2,748
Per Person
View Trip
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Departures: Mar 2026 to Nov 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+7 more), Barbados, Sint Maarten, Virgin Islands, Cayman Islands, Jamaica, Honduras, Mexico
Inside
$2,169
Oceanview
$2,349
Balcony
$2,657
Suite
$6,796
From
US$2,169
Per Person
View Trip
Cruise

8 Days (7 Nights) Philipsburg to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departure: 21 March 2026
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe
Inside
-
Oceanview
$9,320
Balcony
$11,920
Suite
$12,790
From
US$9,320
Per Person
View Trip
Cruise

15 Days (14 Nights) Tampa to Miami
Cruise Line: Regent Seven Seas
Departure: 21 December 2026
Visit: USA, Cayman Islands, Jamaica, Aruba (+5 more), Curacao, Bonaire, Saint Kitts and Nevis, Saint Martin, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,038
Suite
$10,410
From
US$9,038
Save 15,760
Per Person
View Trip
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 09 January 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,240
Suite
$9,920
From
US$6,240
Save 1,560
Per Person
View Trip
Cruise
 (3)

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Departure: 17 February 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands (+6 more), Saint Kitts and Nevis, Saint Barthelemy, Saint Martin, Mexico, Belize, Honduras
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$4,752
Oceanview
$6,159
Balcony
$7,371
Suite
$10,378
From
US$4,752
Save 4,946
Per Person
View Trip
Cruise

15 Days (14 Nights) Saint John's to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Nov 2027 to Mar 2028
Visit: Antigua and Barbuda, Saint Kitts and Nevis, Guadeloupe, Saint Barthelemy (+4 more), Virgin Islands, Puerto Rico, Sint Maarten, Montserrat
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,667
Balcony
-
Suite
$15,208
From
US$11,667
Save 12,828
Per Person
View Trip
Cruise
 (13)

15 Days (14 Nights) Miami to Miami
Cruise Line: Cunard
Departure: 23 December 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Saint Vincent, Barbados, Saint Lucia, Saint Martin
Inside
$3,129
Oceanview
$3,679
Balcony
$4,229
Suite
$11,618
From
US$3,129
Per Person
View Trip
Results: 181-210 of 537

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