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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 507 unique cruise itineraries with 805 past traveler reviews from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 670 departures starting between April 2026 and April 2028.
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507 Cruises (670 Cruise Departures)
15 Day An Extended Journey of Blissful Escapes & Shoreline Splendour with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 08 November 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Virgin Islands (+4 more), Saint Barthelemy, Puerto Rico, Anguilla, Antigua and Barbuda
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,800
From
US$7,800
Per Person
View Trip
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
Inside
-
Oceanview
$6,100
Balcony
$6,900
Suite
$10,000
From
US$6,100
Per Person
View Trip
15 Day Emerald East Coast with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to New York
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 09 April 2027
Visit: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Saint Lucia, Saint Barthelemy, Puerto Rico, Bermuda
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,799
Suite
$14,299
From
US$13,799
Save 13,799
Per Person
View Trip
18 Day Bermuda & Eastern Caribbean Cruise: Sint Maarten, Antigua & Tobago with Azamara Cruises
Cruise
 (5)

18 Days (17 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$4,019
Oceanview
$4,719
Balcony
$5,909
Suite
$9,479
From
US$4,019
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
$5,829
Oceanview
$7,049
Balcony
$8,729
Suite
$13,909
From
US$5,829
Per Person
View Trip
17 Day Caribbean Cruise: New York, Bermuda & Barbados with Azamara Cruises
Cruise
 (3)

17 Days (16 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 29 October 2026
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$3,739
Oceanview
$4,609
Balcony
$5,389
Suite
$8,889
From
US$3,739
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,529
Oceanview
$2,079
Balcony
$2,649
Suite
$4,619
From
US$1,529
Per Person
View Trip
8 Day Caribbean escapade with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Visit: USA, Bahamas, Turks and Caicos Islands, Puerto Rico
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,432
From
US$6,432
Save 1,058
Per Person
View Trip
8 Day Caribbean Escapade with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 21 November 2026
Visit: Puerto Rico, Turks and Caicos Islands, Bahamas, USA
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,432
From
US$6,432
Save 1,058
Per Person
View Trip
29 Day Transatlantic Crossing And Caribbean Celebration with Cunard
Cruise
 (6)

29 Days (28 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 14 December 2027
Visit: England, USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Bonus Onboard Credit
Inside
$3,919
Oceanview
$5,499
Balcony
$5,730
Suite
$15,439
From
US$3,919
Per Person
View Trip
28 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

28 Days (27 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 12 November 2027
Visit: England, USA, Virgin Islands, Saint Kitts and Nevis (+4 more), Saint Lucia, Barbados, Dominica, Saint Martin
Bonus Onboard Credit
Inside
$3,489
Oceanview
$4,889
Balcony
$5,099
Suite
$12,239
From
US$3,489
Per Person
View Trip
27 Day Azure To Iberia with Regent Seven Seas
Cruise

27 Days (26 Nights) Panama City to Lisbon
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 14 March 2028
Visit: Panama, Colombia, Aruba, Curacao (+7 more), Grenada, Dominica, Virgin Islands, USA, Bermuda, Portugal, Spain
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$23,549
Suite
$24,499
From
US$23,549
Save 23,549
Per Person
View Trip
24 Day A Grand Journey Into Island Whispers & Beauty-Rich Shores with Explora Journeys
Cruise

24 Days (23 Nights) San Juan to Barcelona
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 01 March 2027
Visit: Puerto Rico, Antigua and Barbuda, Anguilla, Virgin Islands (+5 more), Turks and Caicos Islands, USA, Saint Martin, Portugal, Spain
Inside
-
Oceanview
-
Balcony
-
Suite
$11,480
From
US$11,480
Per Person
View Trip
20 Day Yacht Harbors & Atlantic Crossing with Seabourn
Cruise

20 Days (19 Nights) Philipsburg to Lisbon
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 18 March 2028
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Saint Vincent, Grenada, Barbados, Saint Lucia, Portugal
Inside
-
Oceanview
-
Balcony
$8,819
Suite
$14,579
From
US$8,819
Per Person
View Trip
29 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

29 Days (28 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 27 February 2028
Visit: England, USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Inside
$4,709
Oceanview
$6,259
Balcony
$6,359
Suite
$15,959
From
US$4,709
Per Person
View Trip
21 Day Transatlantic Crossing And Caribbean Celebration with Cunard
Cruise
 (6)

21 Days (20 Nights) London to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 14 December 2027
Visit: England, USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Bonus Onboard Credit
Inside
$3,053
Oceanview
-
Balcony
$4,328
Suite
$10,989
From
US$3,053
Per Person
View Trip
20 Day Yachtsman's Caribbean & Atlantic Passage with Seabourn
Cruise

20 Days (19 Nights) Philipsburg to Lisbon
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 20 March 2027
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Saint Vincent, Grenada, Barbados, Saint Lucia, Portugal
Yours to Explore
Inside
-
Oceanview
-
Balcony
$10,199
Suite
$20,699
From
US$10,199
Per Person
View Trip
26 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

26 Days (25 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 10 November 2026
Visit: England, USA, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Bonus Onboard Credit
Inside
$3,460
Oceanview
$4,225
Balcony
$4,684
Suite
$16,339
From
US$3,460
Per Person
View Trip
21 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

21 Days (20 Nights) London to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 12 November 2027
Visit: England, USA, Virgin Islands, Saint Kitts and Nevis (+4 more), Saint Lucia, Barbados, Dominica, Saint Martin
Bonus Onboard Credit
Inside
$2,819
Oceanview
$3,702
Balcony
$3,889
Suite
$10,329
From
US$2,819
Per Person
View Trip
31 Day Transatlantic Crossing And Caribbean Celebration with Cunard
Cruise
 (6)

31 Days (30 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 12 December 2026
Visit: England, USA, Virgin Islands, Saint Martin (+4 more), Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Bonus Onboard Credit
Inside
$4,414
Oceanview
$5,408
Balcony
$5,731
Suite
-
From
US$4,414
Per Person
View Trip
26 Day Miami to Lisbon with Silversea
Cruise
 (1)

26 Days (25 Nights) Miami to Lisbon
Cruise Line: Silversea
Ship: Silver Nova
Departure: 22 February 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy (+4 more), Antigua and Barbuda, Saint Kitts and Nevis, Spain, Portugal
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$9,700
Suite
$14,800
From
US$9,700
Per Person
View Trip
21 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

21 Days (20 Nights) London to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 27 February 2028
Visit: England, USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Inside
$3,509
Oceanview
$4,859
Balcony
$5,009
Suite
$12,759
From
US$3,509
Per Person
View Trip
19 Day Transatlantic Crossing And Eastern Caribbean with Cunard
Cruise
 (6)

19 Days (18 Nights) London to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 10 November 2026
Visit: England, USA, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Bonus Onboard Credit
Inside
$2,202
Oceanview
-
Balcony
-
Suite
$10,552
From
US$2,202
Per Person
View Trip
14 Day Atlantic Crossing with Seabourn
Cruise

14 Days (13 Nights) Lisbon to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 14 November 2027
Visit: Portugal, Antigua and Barbuda, Saint Kitts and Nevis, Martinique, Barbados
Yours to Explore
Inside
-
Oceanview
-
Balcony
$6,289
Suite
$10,499
From
US$6,289
Per Person
View Trip
24 Day Transatlantic Crossing And Caribbean Celebration with Cunard
Cruise
 (6)

24 Days (23 Nights) New York to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 19 December 2026
Visit: USA, Virgin Islands, Saint Martin, Barbados (+4 more), Saint Lucia, Dominica, Saint Kitts and Nevis, England
Bonus Onboard Credit
Inside
$3,568
Oceanview
-
Balcony
$4,531
Suite
-
From
US$3,568
Per Person
View Trip
35 Day Caribbean with Cunard
Cruise
 (6)

35 Days (34 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 11 January 2027
Visit: England, Portugal, Saint Kitts and Nevis, Barbados (+7 more), Saint Lucia, Grenada, Dominica, Antigua and Barbuda, Dominican Republic, Saint Martin, Spain
Bonus Onboard Credit
Inside
$5,069
Oceanview
$7,369
Balcony
$7,869
Suite
$23,299
From
US$5,069
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
Inside
$3,739
Oceanview
$4,839
Balcony
$5,189
Suite
$15,039
From
US$3,739
Per Person
View Trip
28 Day Spain And Eastern Caribbean with Cunard
Cruise
 (13)

28 Days (27 Nights) Barcelona to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 29 October 2027
Visit: Spain, USA, Virgin Islands, Saint Kitts and Nevis (+4 more), Grenada, Barbados, Saint Lucia, Saint Martin
Inside
$4,139
Oceanview
$4,939
Balcony
$5,989
Suite
$14,989
From
US$4,139
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: 19 November 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Saint Martin, England
Bonus Onboard Credit
Inside
$2,679
Oceanview
$3,629
Balcony
$3,709
Suite
$9,289
From
US$2,679
Per Person
View Trip
36 Day Caribbean with Cunard
Cruise
 (6)

36 Days (35 Nights) London to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 11 January 2028
Visit: England, Spain, Saint Martin, Grenada (+8 more), Saint Lucia, Barbados, Dominica, Bonaire, Curacao, Saint Kitts and Nevis, Virgin Islands, Portugal
Inside
$4,899
Oceanview
$7,699
Balcony
$7,799
Suite
$19,699
From
US$4,899
Per Person
View Trip
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