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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 522 unique cruise itineraries with 845 past traveler reviews from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 684 departures starting between February 2026 and April 2028.
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522 Cruises (684 Cruise Departures)
15 Day Caribbean Cruise: San Juan, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Dec 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
$3,503
Oceanview
$4,269
Balcony
$5,424
Suite
$8,392
From
US$3,503
Save 94
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Apr 2028
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+4 more), Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Saint Martin
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$4,574
Balcony
-
Suite
$6,272
From
US$4,574
Save 7,173
Per Person
View Trip
11 Day Fantasy Islands with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 27 December 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Dominican Republic
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,031
Oceanview
$4,049
Balcony
$4,971
Suite
$6,717
From
US$3,031
Save 3,167
Per Person
View Trip
16 Day Leeward Isles Serenade with Oceania Cruises
Cruise
 (1)

16 Days (15 Nights) Tampa to Tampa
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 03 March 2026
Visit: USA, Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda, Dominica, Saint Kitts and Nevis
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
$3,912
Oceanview
$4,455
Balcony
-
Suite
-
From
US$3,912
Save 6,086
Per Person
View Trip
10 Day Tropical Retreat: Roundtrip Bridgetown with Emerald Cruises
New ReleaseCruise
 (3)

10 Days (9 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departures: Dec 2027 to Dec 2027
Visit: Barbados, Saint Lucia, Martinique, Saint Vincent
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,582
Balcony
-
Suite
$7,764
From
US$5,582
Save 8,166
Per Person
View Trip
17 Day An Extended Journey Through Ancient Marvels & Glittering Shores with Explora Journeys
Cruise

17 Days (16 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 January 2027
Visit: USA, Jamaica, Guatemala, Honduras (+6 more), Belize, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,000
Suite
$7,910
From
US$7,000
Per Person
View Trip
12 Day Bridgetown to Bridgetown with Silversea
Cruise

12 Days (11 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 04 January 2027
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+5 more), Aruba, Curacao, Bonaire, Grenada, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,480
Balcony
$5,280
Suite
$4,880
From
US$4,480
Save 1,120
Per Person
View Trip
10 Day A Journey from From Hidden Shores to Timeless Elegance with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 11 January 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,935
Suite
$5,565
From
US$4,935
Per Person
View Trip
9 Day Splendours of the Caribbean with Scenic
New ReleaseCruise

9 Days (8 Nights) Saint John's to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse II
Departure: 15 October 2027
Visit: Antigua and Barbuda, Saint Barthelemy, Virgin Islands, Montserrat (+5 more), Martinique, Saint Lucia, Saint Vincent, Trinidad and Tobago, Barbados
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,917
Suite
$8,208
From
US$7,917
Save 11,473
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
11 Day Lesser Antilles Journey with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 19 December 2026
Visit: USA, Virgin Islands, Dominica, Antigua and Barbuda, Saint Kitts and Nevis
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,466
Suite
$8,495
From
US$7,466
Save 13,132
Per Person
View Trip
8 Day A Journey into Tropical Utopia & Art Deco Flair with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 02 March 2026
Visit: Puerto Rico, Antigua and Barbuda, Anguilla, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,825
Suite
$4,310
From
US$3,825
Per Person
View Trip
11 Day Tropical Island Havens with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departures: Dec 2026 to Mar 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis
Multiple Deals Available
Inside
-
Oceanview
-
Balcony
$3,613
Suite
$6,038
From
US$3,613
Save 4,301
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: 28 February 2027
Visit: Barbados, Saint Lucia, Saint Barthelemy, Virgin Islands, Antigua and Barbuda, Dominica, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,240
Balcony
$4,720
Suite
$4,320
From
US$4,240
Save 1,060
Per Person
View Trip
8 Day A Journey From San Juan To Miami with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 11 March 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Martin, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,095
Suite
$5,760
From
US$4,095
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,415
From
US$3,915
Per Person
View Trip
10 Day Colours of the Caribbean: Antigua to San Juan with Emerald Cruises
New ReleaseCruise

10 Days (9 Nights) Saint John's to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 11 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Guadeloupe, Dominica, Saint Kitts and Nevis, Antigua and Barbuda
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,063
Balcony
-
Suite
$8,342
From
US$6,063
Save 8,427
Per Person
View Trip
15 Day Discover the Pearls of the Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 06 December 2026
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Bonaire, Virgin Islands
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$9,553
From
US$9,553
Save 12,227
Per Person
View Trip
11 Day Classic Canal & Tropics with Oceania Cruises
Cruise
 (1)

11 Days (10 Nights) Panama City to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 04 April 2026
Visit: Panama, Colombia, Curacao, Aruba, Jamaica, Cayman Islands, USA
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
$2,720
Oceanview
$2,939
Balcony
$4,501
Suite
-
From
US$2,720
Save 4,078
Per Person
View Trip
11 Day Southern Caribbean & St. Barts with Seabourn
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departures: Nov 2027 to Dec 2027
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Montserrat, Saint Barthelemy, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
$4,919
Balcony
$5,899
Suite
$8,839
From
US$4,919
Save 80
Per Person
View Trip
19 Day Caribbean Holiday Cruise: San Juan, St. Barts & Curacao with Azamara Cruises
Cruise
 (3)

19 Days (18 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+8 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis
Azamara Always Included
Exclusive Savings
Inside
$5,356
Oceanview
$5,647
Balcony
$6,986
Suite
$11,060
From
US$5,356
Save 133
Per Person
View Trip
8 Day Caribbean Yachting Hideaways with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Montserrat, Antigua and Barbuda
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$4,843
Balcony
-
Suite
$6,614
From
US$4,843
Save 7,404
Per Person
View Trip
17 Day Leeward Island Holiday with Seabourn
Cruise
 (1)

17 Days (16 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 20 December 2026
Visit: USA, Puerto Rico, Anguilla, Saint Kitts and Nevis (+8 more), Saint Martin, Guadeloupe, Martinique, Saint Lucia, Dominica, Montserrat, Antigua and Barbuda, Virgin Islands
Explore More
Exclusive Savings
Inside
-
Oceanview
$9,195
Balcony
$11,748
Suite
$16,692
From
US$9,195
Save 154
Per Person
View Trip
9 Day Southern Caribbean Cruise: Martinique, Grenada & U.S. Virgin Islands with Azamara Cruises
Cruise
 (4)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,229
Oceanview
$2,724
Balcony
$3,306
Suite
$5,013
From
US$2,229
Per Person
View Trip
10 Day Sunlit Caribbean Gems with Oceania Cruises
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 12 December 2026
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,273
Suite
$5,261
From
US$3,273
Save 3,425
Per Person
View Trip
8 Day A Journey Of Blissful Escapes & Island Splendour with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands, Dominican Republic, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,125
Suite
$4,760
From
US$4,125
Per Person
View Trip
9 Day A Journey Into Tropical Idylls & Mayan Mystery with Explora Journeys
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 December 2026
Visit: USA, Mexico, Guatemala, Belize, Honduras
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,375
Suite
$4,970
From
US$4,375
Per Person
View Trip
11 Day Blissful Bvi with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 05 April 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,391
Suite
$7,665
From
US$6,391
Save 12,007
Per Person
View Trip
13 Day Radiant Island Retreats with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 27 February 2027
Visit: USA, Cayman Islands, Jamaica, Aruba (+4 more), Curacao, Bonaire, Dominican Republic, Bahamas
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,345
Suite
$7,401
From
US$4,345
Save 4,553
Per Person
View Trip
8 Day Yachtsman's Caribbean with Seabourn
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 28 March 2026
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique, Saint Vincent, Grenada, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,126
Suite
$8,341
From
US$5,126
Save 92
Per Person
View Trip
Results: 61-90 of 522

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