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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 Secluded Isles & Coastal Havens with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 January 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Turks and Caicos Islands (+4 more), USA, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$9,000
From
US$9,000
Per Person
View Trip
11 Day A Journey of Reggae Beats & Hypnotic Caribbean Wonders with Explora Journeys
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 13 December 2027
Visit: USA, Jamaica, Bonaire, Curacao, Aruba, Bahamas
Inside
-
Oceanview
-
Balcony
-
Suite
$5,215
From
US$5,215
Per Person
View Trip
11 Day San Juan to San Juan with Silversea
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departures: Jan 2028 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,900
Balcony
$5,500
Suite
$10,700
From
US$4,900
Save 1,500
Per Person
View Trip
15 Day Discover the Pearls of the Caribbean with Emerald Cruises
Cruise

15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Mar 2028
Visit: Saint Martin, Saint Kitts and Nevis, Anguilla, Virgin Islands (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Inside
-
Oceanview
$12,690
Balcony
-
Suite
$20,150
From
US$12,690
Per Person
View Trip
11 Day Southern Caribbean & St. Barts Holiday with Seabourn
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 18 December 2027
Visit: USA, Puerto Rico, Anguilla, Montserrat, Saint Kitts and Nevis, Virgin Islands
Yours to Explore
Inside
-
Oceanview
$4,999
Balcony
$5,999
Suite
$8,999
From
US$4,999
Per Person
View Trip
16 Day An Extended Journey Through Caribbean Treasures & Peaceful Nature with Explora Journeys
Cruise

16 Days (15 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 21 January 2027
Visit: USA, Virgin Islands, Anguilla, Martinique (+5 more), Saint Kitts and Nevis, Saint Martin, Puerto Rico, Antigua and Barbuda, Turks and Caicos Islands
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$8,040
From
US$8,040
Per Person
View Trip
13 Day Miami, Fl to Miami, Fl with Silversea
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 24 December 2027
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Virgin Islands, Turks and Caicos Islands
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,500
Balcony
$6,700
Suite
$11,100
From
US$5,500
Save 1,500
Per Person
View Trip
8 Day A Journey Through A Caribbean Tapestry Of Serenity & Splendour with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Turks and Caicos Islands, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$3,850
From
US$3,850
Per Person
View Trip
9 Day A Journey of Caribbean Enchantment & Tranquil Shores with Explora Journeys
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visit: Puerto Rico, Saint Martin, Guadeloupe, Grenada, Saint Lucia, Dominican Republic, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,640
From
US$5,640
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
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,899
Suite
$6,199
From
US$3,899
Save 4,599
Per Person
View Trip
15 Day Caribbean Celebration with Cunard
Cruise
 (6)

15 Days (14 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 19 December 2026
Visit: USA, Virgin Islands, Saint Martin, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Bonus Onboard Credit
Inside
$2,899
Oceanview
$3,699
Balcony
$3,729
Suite
$12,299
From
US$2,899
Per Person
View Trip
15 Day An Extended Journey of Maritime Soul & Island Zest with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 25 October 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+5 more), Saint Martin, Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Anguilla
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$8,510
From
US$8,510
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
Inside
$3,799
Oceanview
$4,809
Balcony
$5,859
Suite
$8,929
From
US$3,799
Per Person
View Trip
8 Day A Journey Through Art Deco Wonders & Caribbean Adventures with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 23 December 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$4,745
From
US$4,745
Per Person
View Trip
19 Day An Extended Journey of Coastal Marvels & Caribbean Dreams with Explora Journeys
Cruise

19 Days (18 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 11 January 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands (+4 more), Jamaica, Guatemala, Honduras, Belize
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$8,260
From
US$8,260
Per Person
View Trip
11 Day Golden Caribbean Strands with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 23 February 2027
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Dominican Republic, Bahamas
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,049
Oceanview
$3,799
Balcony
$4,499
Suite
$6,199
From
US$3,049
Save 3,049
Per Person
View Trip
17 Day Caribbean Christmas Cruise: Barbados, St. Lucia & St. Thomas with Azamara Cruises
Cruise
 (3)

17 Days (16 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 12 December 2026
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+8 more), Saint Martin, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy, Martinique, Saint Vincent, Trinidad and Tobago
Azamara Always Included
Inside
$4,299
Oceanview
$4,559
Balcony
$5,689
Suite
$8,909
From
US$4,299
Per Person
View Trip
8 Day History and Culture Visiting Caribbean Jewels with Ponant
Cruise

8 Days (7 Nights) Pointe-A-Pitre to Marigot
Cruise Line: Ponant
Ship: Le Ponant
Departures: Apr 2026 to Apr 2027
Visit: Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Inside
-
Oceanview
$8,770
Balcony
$12,440
Suite
$13,390
From
US$8,770
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
Inside
$5,639
Oceanview
$6,619
Balcony
$7,699
Suite
-
From
US$5,639
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 20 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,186
Balcony
-
Suite
$7,824
From
US$6,186
Save 609
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,180
From
US$5,180
Per Person
View Trip
16 Day An Extended Journey Of Cultural Treasures & Seaside Harmony with Explora Journeys
Cruise

16 Days (15 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 December 2026
Visit: USA, Mexico, Guatemala, Belize (+6 more), Honduras, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,965
From
US$6,965
Per Person
View Trip
8 Day Pearls of the Caribbean with Ponant
Cruise
 (1)

8 Days (7 Nights) Vieux Fort to Vieux Fort
Cruise Line: Ponant
Ship: Le Bougainville
Departures: Feb 2027 to Mar 2027
Visit: Saint Lucia, Saint Vincent, Guadeloupe, England
Inside
-
Oceanview
-
Balcony
$4,760
Suite
$7,090
From
US$4,760
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
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,974
Balcony
-
Suite
$8,887
From
US$6,974
Save 1,196
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
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$9,884
Balcony
-
Suite
$12,315
From
US$9,884
Save 1,511
Per Person
View Trip
11 Day Riviera Chic & Caribbean Cool with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 29 November 2026
Visit: USA, Puerto Rico, Saint Barthelemy, Sint Maarten, Virgin Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,549
Suite
$11,049
From
US$10,549
Save 10,549
Per Person
View Trip
9 Day A Journey Of Spectacular Festivities & Caribbean Wonders with Explora Journeys
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 December 2026
Visit: Puerto Rico, Antigua and Barbuda, Guadeloupe, Virgin Islands, Dominican Republic, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,840
From
US$6,840
Per Person
View Trip
22 Day Caribbean with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire (+7 more), Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Bonus Onboard Credit
Inside
$2,139
Oceanview
$2,419
Balcony
$2,969
Suite
$7,589
From
US$2,139
Per Person
View Trip
8 Day Reefs Of The Maya with Oceania Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 21 November 2027
Visit: USA, Mexico, Honduras, Belize
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$1,899
Oceanview
$1,999
Balcony
$3,099
Suite
$4,399
From
US$1,899
Save 1,899
Per Person
View Trip
8 Day A Journey From Exciting Escapades To Idyllic Tranquillity with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 01 March 2027
Visit: Puerto Rico, Antigua and Barbuda, Anguilla, Virgin Islands, Turks and Caicos Islands, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,125
From
US$4,125
Per Person
View Trip
Results: 181-210 of 507

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