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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 494 unique cruise itineraries with 812 past traveler reviews from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 648 departures starting between March 2026 and April 2028.
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494 Cruises (648 Cruise Departures)
11 Day Miami to San Juan with Silversea
Cruise

11 Days (10 Nights) Miami to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 10 December 2026
Visit: USA, Virgin Islands, Saint Martin, Saint Kitts and Nevis (+4 more), Guadeloupe, Martinique, Montserrat, Puerto Rico
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
$4,880
Balcony
$5,680
Suite
$8,560
From
US$4,880
Save 1,220
Per Person
View Trip
8 Day A Journey Through Captivating Caribbean Culture & Sunlit Shores with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 12 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Guadeloupe, Dominican Republic, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,425
From
US$4,425
Per Person
View Trip
15 Day Festive Caribbean Frolic with Oceania Cruises
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 22 December 2027
Visit: USA, Aruba, Curacao, Bonaire (+6 more), Grenada, Saint Vincent, Saint Lucia, Martinique, Dominica, Virgin Islands
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$4,302
Oceanview
$4,835
Balcony
$7,115
Suite
$9,831
From
US$4,302
Save 4,496
Per Person
View Trip
18 Day Caribbean Carried Away with Oceania Cruises
Cruise
 (3)

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
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
Your World Included Credit
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
13 Day Antillean Island Sojourn with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 25 November 2026
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy, Martinique, Guadeloupe, Antigua and Barbuda
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,317
Suite
$5,966
From
US$4,317
Save 6,081
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 21 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Exclusive Savings
Inside
$3,717
Oceanview
$4,697
Balcony
$5,715
Suite
$8,693
From
US$3,717
Save 82
Per Person
View Trip
8 Day Caribbean Gems with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 12 December 2026
Visit: Barbados, Saint Kitts and Nevis, Guadeloupe, Martinique, Dominica, Saint Lucia
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,933
Suite
$8,343
From
US$3,933
Save 66
Per Person
View Trip
11 Day Classic Canal & Tropics with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Panama City to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 16 January 2028
Visit: Panama, Colombia, Curacao, Aruba, Jamaica, Cayman Islands, USA
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
$3,043
Oceanview
$4,013
Balcony
$4,789
Suite
$6,729
From
US$3,043
Save 3,155
Per Person
View Trip
12 Day Waterfalls & Divers with Regent Seven Seas
Cruise

12 Days (11 Nights) Galveston to Galveston
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 30 November 2026
Visit: USA, Cayman Islands, Honduras, Belize, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,722
Suite
$10,604
From
US$9,722
Save 10,076
Per Person
View Trip
15 Day Sun-kissed Soiree with Regent Seven Seas
Cruise

15 Days (14 Nights) New York to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 04 November 2027
Visit: USA, Bahamas, Dominican Republic, Curacao, Aruba, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,446
Suite
$14,622
From
US$13,446
Save 13,952
Per Person
View Trip
8 Day Bridgetown to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 05 December 2026
Visit: Barbados, Saint Vincent, Martinique, Guadeloupe, Saint Barthelemy, Antigua and Barbuda, Saint Lucia
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,550
Balcony
$5,040
Suite
$4,760
From
US$4,550
Save 1,950
Per Person
View Trip
10 Day Western Caribbean with Cunard
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Mar 2026 to Dec 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Mexico
Bonus Onboard Credit
Inside
$529
Oceanview
$589
Balcony
$1,349
Suite
$2,699
From
US$529
Per Person
View Trip
9 Day A Journey of Endless Sophistication and Island Charm with Explora Journeys
Cruise
 (1)

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 18 March 2026
Visit: USA, Virgin Islands, Guadeloupe, Barbados, Martinique, Saint Kitts and Nevis, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$5,200
From
US$5,200
Per Person
View Trip
21 Day Cultural Currents with Regent Seven Seas
Cruise

21 Days (20 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 26 March 2027
Visit: USA, Bahamas, Mexico, Belize (+7 more), Honduras, Jamaica, Cayman Islands, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$17,831
Suite
$19,987
From
US$17,831
Save 18,467
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 21 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,920
Balcony
$4,480
Suite
$8,760
From
US$3,920
Save 980
Per Person
View Trip
8 Day Cruising the Leeward Islands with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Philipsburg to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Apr 2028
Visit: Sint Maarten, Saint Kitts and Nevis, Anguilla, Virgin Islands, Saint Barthelemy
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$4,615
Balcony
-
Suite
$6,313
From
US$4,615
Save 7,132
Per Person
View Trip
12 Day Americana Coast Cruise: Key West, Tampa & New Orleans with Azamara Cruises
Cruise
 (5)

12 Days (11 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 22 March 2028
Visit: USA, Mexico
Azamara Always Included
Inside
$2,529
Oceanview
$3,024
Balcony
$3,800
Suite
$6,138
From
US$2,529
Per Person
View Trip
8 Day Miami, Fl to Miami, Fl with Silversea
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 17 December 2027
Visit: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,040
Balcony
$3,680
Suite
$5,880
From
US$3,040
Save 760
Per Person
View Trip
11 Day Splendid Sunsets with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 17 February 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,032
Oceanview
$3,808
Balcony
$4,487
Suite
$6,524
From
US$3,032
Save 3,166
Per Person
View Trip
13 Day Caribbean Celebration with Cunard
Cruise
 (13)

13 Days (12 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 17 December 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin
Bonus Onboard Credit
Inside
$1,349
Oceanview
$1,549
Balcony
$1,869
Suite
$3,829
From
US$1,349
Per Person
View Trip
8 Day A Journey from Dominican Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 09 January 2028
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
12 Day Caribbean Breeze: Miami to Antigua with Emerald Cruises
New ReleaseCruise

12 Days (11 Nights) Miami to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 19 February 2028
Visit: USA, Bahamas, Turks and Caicos Islands, Puerto Rico (+4 more), Virgin Islands, Anguilla, Saint Barthelemy, Antigua and Barbuda
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$7,756
Balcony
-
Suite
$10,520
From
US$7,756
Save 10,234
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 26 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Montserrat
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,400
Balcony
$5,040
Suite
$8,200
From
US$4,400
Save 1,100
Per Person
View Trip
8 Day Bridgetown to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departures: Jan 2028 to Jan 2028
Visit: Barbados, Saint Vincent, Martinique, Saint Barthelemy, Dominica, Grenada, Saint Lucia
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,080
Balcony
$4,560
Suite
$4,320
From
US$4,080
Save 1,020
Per Person
View Trip
9 Day Western Caribbean Cruise: Costa Maya, Belize & Cozumel with Azamara Cruises
Cruise
 (8)

9 Days (8 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 14 December 2027
Visit: USA, Mexico, Belize, Honduras
Azamara Always Included
Exclusive Savings
Inside
$5,489
Oceanview
$6,440
Balcony
$7,487
Suite
-
From
US$5,489
Save 150
Per Person
View Trip
8 Day A Journey to Island Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Jan 2028 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
15 Day Windward & Leeward Islands with Seabourn
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 04 December 2027
Visit: USA, Saint Barthelemy, Saint Kitts and Nevis, Martinique (+5 more), Dominica, Montserrat, Antigua and Barbuda, Anguilla, Virgin Islands
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
$6,886
Balcony
$8,356
Suite
$12,276
From
US$6,886
Save 113
Per Person
View Trip
11 Day Bahamian Breeze with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 07 January 2028
Visit: USA, Saint Martin, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,111
Suite
$10,503
From
US$10,111
Save 10,487
Per Person
View Trip
8 Day A Journey From Glorious Shorelines To Nature's Allure with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 March 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,920
From
US$3,920
Per Person
View Trip
15 Day Caribbean Cruise: Barbados, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Nov 2027
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+8 more), Saint Martin, Virgin Islands, Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago
Azamara Always Included
Exclusive Savings
Inside
$3,717
Oceanview
$4,171
Balcony
$5,325
Suite
$8,138
From
US$3,717
Save 93
Per Person
View Trip
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