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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 568 unique cruise itineraries with 784 past traveler reviews from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 819 departures starting between September 2026 and April 2029.
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568 Cruises (819 Cruise Departures)
8 Day A Journey Through Tropical Utopia & Rhythmic Streets with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 March 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,020
From
US$4,020
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
Inside
-
Oceanview
$4,498
Balcony
$5,498
Suite
$7,998
From
US$4,498
Per Person
View Trip
15 Day Caribbean Celebration with Cunard
Cruise
 (13)

15 Days (14 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 23 December 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Saint Vincent, Barbados, Saint Lucia, Saint Martin
Cunard Fare
Value Fare
Inside
$2,269
Oceanview
$2,669
Balcony
$3,109
Suite
$9,399
From
US$2,269
Per Person
View Trip
18 Day Caribbean New Year Cruise: Barbados, Aruba & St. Barts with Azamara Cruises
Cruise
 (4)

18 Days (17 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 28 December 2026
Visit: Barbados, Aruba, Curacao, Saint Lucia (+7 more), Saint Kitts and Nevis, Virgin Islands, Puerto Rico, Saint Barthelemy, Saint Martin, Antigua and Barbuda, USA
Azamara Always Included
Inside
$5,299
Oceanview
$6,059
Balcony
$7,679
Suite
$10,809
From
US$5,299
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 22 February 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,400
Suite
$11,400
From
US$6,400
Save 1,600
Per Person
View Trip
26 Day Europe To The Caribbean with Oceania Cruises
Cruise
 (3)

26 Days (25 Nights) Rome to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 15 November 2026
Visit: Italy, Sicily, Malta, Tunisia (+6 more), Sardinia, Spain, Portugal, Puerto Rico, Dominican Republic, USA
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,149
Suite
$13,799
From
US$10,149
Save 10,149
Per Person
View Trip
15 Day Leeward Island Jewels with Seabourn
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 22 November 2026
Visit: USA, Puerto Rico, Anguilla, Saint Kitts and Nevis (+5 more), Dominica, Martinique, Guadeloupe, Montserrat, Virgin Islands
Inside
-
Oceanview
$7,498
Balcony
$8,698
Suite
$11,298
From
US$7,498
Per Person
View Trip
8 Day Eastern Caribbean Cruise: Sint Maarten, Saint Kitts & Nevis with Azamara Cruises
Cruise
 (5)

8 Days (7 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 28 November 2027
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,949
Oceanview
$2,449
Balcony
$2,979
Suite
$4,519
From
US$1,949
Per Person
View Trip
14 Day Discover the Grenadines & Windwards islands with Emerald Cruises
New ReleaseCruise
 (3)

14 Days (13 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 27 December 2026
Visit: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+4 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Inside
-
Oceanview
-
Balcony
-
Suite
$15,765
From
US$15,765
Per Person
View Trip
15 Day Eastern Caribbean with Cunard
Cruise
 (13)

15 Days (14 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Nov 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Grenada, Barbados, Saint Lucia, Saint Martin
Value Fare + Signature Package
Cunard Fare
Value Fare
Inside
$1,299
Oceanview
$1,699
Balcony
$2,049
Suite
$5,599
From
US$1,299
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra
Departures: Dec 2026 to Mar 2027
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+4 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$3,991
Balcony
-
Suite
$5,390
From
US$3,991
Save 1,804
Per Person
View Trip
14 Day Discover the Hidden Wonders of the Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

14 Days (13 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
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
Inside
-
Oceanview
-
Balcony
-
Suite
$33,445
From
US$33,445
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
Exclusive Savings
Inside
$3,099
Oceanview
$4,099
Balcony
$4,899
Suite
$6,899
From
US$3,099
Save 3,099
Per Person
View Trip
8 Day Southern Caribbean Cruise: Antigua, Grenada & Barbados with Azamara Cruises
Cruise
 (4)

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Dec 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$1,469
Oceanview
$1,839
Balcony
$2,349
Suite
$3,579
From
US$1,469
Per Person
View Trip
6 Day Classic Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

6 Days (5 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 04 December 2028
Visit: Barbados, Saint Vincent, Grenada, Saint Lucia, Martinique
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$3,220
Balcony
-
Suite
$4,390
From
US$3,220
Save 1,425
Per Person
View Trip
13 Day Panama, Colombia & Caribbean Islands with Ponant
Cruise
 (1)

13 Days (12 Nights) Colon to Fort-de-France
Cruise Line: Ponant
Ships: Le Bellot, Le Bougainville
Departures: Mar 2028 to Apr 2028
Visit: Panama, Colombia, Holland, Saint Vincent, Saint Lucia, Guadeloupe, Martinique
Inside
-
Oceanview
-
Balcony
$7,680
Suite
$12,200
From
US$7,680
Per Person
View Trip
8 Day Pearls of the Caribbean with Ponant
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: Ponant
Ship: Le Bougainville
Departures: Dec 2026 to Feb 2027
Visit: Martinique, Saint Vincent, Saint Lucia, Guadeloupe
Inside
-
Oceanview
-
Balcony
$5,270
Suite
$7,940
From
US$5,270
Per Person
View Trip
18 Day Holiday Horizons with Oceania Cruises
Cruise
 (3)

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 20 December 2027
Visit: USA, Mexico, Belize, Honduras (+6 more), Bahamas, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Dominican Republic
Your World Inclusions
Exclusive Savings
Inside
$5,299
Oceanview
$6,649
Balcony
$8,099
Suite
$10,949
From
US$5,299
Save 5,299
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 18 December 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Martinique
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,930
Suite
$14,000
From
US$6,930
Save 2,970
Per Person
View Trip
8 Day A Journey into Dominican Charm & Caribbean Splendour with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 30 January 2028
Visit: USA, Dominican Republic, Virgin Islands, Anguilla, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$4,020
From
US$4,020
Per Person
View Trip
21 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

21 Days (20 Nights) New York to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 06 March 2028
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin, England
Cunard Fare
Inside
-
Oceanview
-
Balcony
-
Suite
$12,079
From
US$12,079
Per Person
View Trip
14 Day Caribbean Cruise: San Juan, Antigua & St. Lucia with Azamara Cruises
Cruise
 (4)

14 Days (13 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 05 December 2026
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
Inside
-
Oceanview
$3,789
Balcony
$5,689
Suite
$7,849
From
US$3,789
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 20 January 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,640
Suite
$11,800
From
US$6,640
Save 1,660
Per Person
View Trip
8 Day Grenadines & Windwards yachting with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Sakara
Departures: Nov 2026 to Apr 2029
Visit: Barbados, Grenada, Saint Vincent
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$4,715
Balcony
-
Suite
$6,221
From
US$4,715
Save 1,636
Per Person
View Trip
25 Day Bermuda & Eastern Caribbean Cruise: Tortola, Barbados & Saint Kitts with Azamara Cruises
Cruise
 (5)

25 Days (24 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+10 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Azamara Always Included
Inside
$5,949
Oceanview
$7,179
Balcony
$8,859
Suite
$14,029
From
US$5,949
Per Person
View Trip
16 Day Broadway To The ABC Islands with Oceania Cruises
Cruise
 (1)

16 Days (15 Nights) New York to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 06 November 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+5 more), Bonaire, Curacao, Aruba, Jamaica, Cayman Islands
Your World Inclusions
Exclusive Savings
Inside
$4,149
Oceanview
$4,449
Balcony
$6,999
Suite
$9,599
From
US$4,149
Save 4,149
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
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,020
From
US$4,020
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
Inside
-
Oceanview
$7,298
Balcony
$7,998
Suite
$11,998
From
US$7,298
Per Person
View Trip
14 Day Caribbean Celebration with Cunard
Cruise
 (6)

14 Days (13 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 21 December 2027
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Cunard Fare
Value Fare
Value Fare + Signature Package
Inside
$2,259
Oceanview
$3,079
Balcony
$3,209
Suite
$8,899
From
US$2,259
Per Person
View Trip
9 Day Caribbean Cruise: Curacao, Aruba & St.lucia with Azamara Cruises
Cruise
 (4)

9 Days (8 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 28 December 2026
Visit: Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$2,239
Oceanview
$2,749
Balcony
$3,469
Suite
$5,599
From
US$2,239
Per Person
View Trip
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