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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 537 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 700 departures starting between January 2026 and April 2028.
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537 Cruises (700 Cruise Departures)
8 Day Yachtsman's Harbors with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 05 February 2027
Visit: USA, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,737
Suite
$4,434
From
US$2,737
Save 2,861
Per Person
View Trip
9 Day San Juan to Miami, Fl with Silversea
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, USA
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,600
Suite
$9,340
From
US$5,600
Save 1,400
Per Person
View Trip
8 Day A Journey Through Caribbean Gems & Multi-coloured Coasts with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 December 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, Turks and Caicos Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,445
From
US$3,850
Per Person
View Trip
12 Day Miami to Miami with Silversea
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 05 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,390
Suite
$9,990
From
US$5,390
Save 2,310
Per Person
View Trip
9 Day A Journey Through Majestic Island Paradises & Radiant Cultures with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 November 2027
Visit: USA, Turks and Caicos Islands, Saint Barthelemy, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,450
Suite
$5,200
From
US$4,450
Per Person
View Trip
8 Day Eastern Caribbean Cruise: Barbados, Saint Kittsand Nevis & Puerto Rico with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 07 December 2027
Visit: Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico, USA
Azamara Always Included
Inside
$1,809
Oceanview
$2,178
Balcony
$2,750
Suite
$4,040
From
US$1,809
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 Ray
Departure: 03 January 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,240
Suite
$10,600
From
US$6,240
Save 1,560
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
Departure: 07 February 2026
Visit: Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Inside
-
Oceanview
$10,420
Balcony
$13,340
Suite
-
From
US$10,420
Per Person
View Trip
16 Day An Extended Journey Through Spectacular Nature And Historic Wonders with Explora Journeys
Cruise
 (1)

16 Days (15 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 03 March 2026
Visit: Puerto Rico, Grenada, Saint Vincent, Barbados (+8 more), Martinique, Saint Barthelemy, Saint Kitts and Nevis, Anguilla, Antigua and Barbuda, Saint Martin, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,830
Suite
$12,240
From
US$7,830
Per Person
View Trip
8 Day Tropical Retreats with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 19 February 2026
Visit: USA, Mexico, Belize, Honduras
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,807
Suite
-
From
US$3,807
Save 3,991
Per Person
View Trip
27 Day Antilles & Atlantic Gems with Oceania Cruises
Cruise

27 Days (26 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 09 March 2026
Visit: USA, Aruba, Curacao, Grenada (+5 more), Saint Vincent, Martinique, Virgin Islands, Bermuda, Bahamas
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,096
Suite
-
From
US$12,096
Save 12,702
Per Person
View Trip
19 Day Bridgetown to Bridgetown with Silversea
Cruise

19 Days (18 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 29 February 2028
Visit: Barbados, Saint Vincent, Grenada, Curacao (+10 more), Aruba, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Lucia, Guadeloupe, Saint Martin, Virgin Islands, Saint Kitts and Nevis, Dominica
All-Inclusive Fare
Inside
-
Oceanview
$7,100
Balcony
$8,100
Suite
$7,400
From
US$7,100
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
Inside
$3,129
Oceanview
$3,679
Balcony
$4,229
Suite
$11,618
From
US$3,129
Per Person
View Trip
17 Day An Extended Journey of Caribbean Celebrations & Tropical Idylls with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 December 2026
Visit: Puerto Rico, Antigua and Barbuda, Guadeloupe, Virgin Islands (+4 more), Dominican Republic, USA, Saint Barthelemy, Saint Kitts and Nevis
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$9,765
Suite
$11,375
From
US$9,765
Per Person
View Trip
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise

15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 12 February 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,645
Balcony
-
Suite
$15,040
From
US$11,645
Save 12,335
Per Person
View Trip
10 Day Calypso Sunsets with Oceania Cruises
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 28 December 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Belize, Mexico
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,612
Suite
$5,746
From
US$3,612
Save 3,786
Per Person
View Trip
8 Day A Journey Across Turquoise Seas and Timeless Streets with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 19 February 2028
Visit: Puerto Rico, Saint Martin, Guadeloupe, Anguilla, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
18 Day Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba with Azamara Cruises
Cruise
 (4)

18 Days (17 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+10 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Bonaire, Curacao, Aruba, Dominican Republic, Bahamas, USA
Azamara Always Included
Exclusive Savings
Inside
$4,623
Oceanview
$5,670
Balcony
$6,960
Suite
$10,569
From
US$4,623
Save 106
Per Person
View Trip
18 Day An Extended Journey Through Timeless Mysteries And Modern Marvels with Explora Journeys
Cruise
 (1)

18 Days (17 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2026
Visit: USA, Mexico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$10,165
Suite
$10,545
From
US$10,165
Per Person
View Trip
16 Day Southern Caribbean Cruise: Dominica, Bequia & Grenada with Azamara Cruises
Cruise
 (4)

16 Days (15 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 12 December 2027
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+7 more), Saint Martin, Virgin Islands, Puerto Rico, Antigua and Barbuda, Saint Vincent, Grenada, Trinidad and Tobago
Azamara Always Included
Exclusive Savings
Inside
$3,844
Oceanview
$4,824
Balcony
$5,978
Suite
$9,179
From
US$3,844
Save 85
Per Person
View Trip
15 Day Discover Island Rhythms & Coastal Dreams with Emerald Cruises
Cruise

15 Days (14 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Turks and Caicos Islands, Bahamas, USA
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$12,492
Balcony
-
Suite
$16,033
From
US$12,492
Save 13,188
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
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,636
Suite
$7,012
From
US$4,636
Save 4,862
Per Person
View Trip
12 Day Americana Coast Cruise: Key West, Tampa & New Orleans with Azamara Cruises
Cruise
 (4)

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
$2,429
Oceanview
$3,024
Balcony
$3,800
Suite
$6,138
From
US$2,429
Per Person
View Trip
8 Day A Journey Through Stunning Scenery & Charming Caribbean Culture with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 29 January 2027
Visit: USA, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,340
From
US$3,850
Per Person
View Trip
8 Day Sea, Sun & Salsa with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 20 November 2027
Visit: USA, Belize, Guatemala, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,063
Suite
$5,259
From
US$5,063
Save 10,235
Per Person
View Trip
8 Day Caribbean Yachting Discovery with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Saint John's to San Juan
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia
Departures: Feb 2026 to Mar 2028
Visit: Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Virgin Islands, Puerto Rico
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$4,787
Balcony
-
Suite
$4,816
From
US$4,787
Save 7,412
Per Person
View Trip
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,210
Suite
$8,295
From
US$7,210
Per Person
View Trip
8 Day History and Culture Visiting Caribbean jewels with Ponant
Cruise

8 Days (7 Nights) Philipsburg to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departure: 21 March 2026
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe
Inside
-
Oceanview
$9,320
Balcony
$11,920
Suite
$12,790
From
US$9,320
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
Departure: 11 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy (+5 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,760
Balcony
$4,320
Suite
$8,980
From
US$3,760
Save 940
Per Person
View Trip
13 Day Dutch Isles Delights with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 09 March 2026
Visit: USA, Aruba, Curacao, Grenada, Saint Vincent, Martinique, Virgin Islands
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,236
Suite
-
From
US$6,236
Save 6,562
Per Person
View Trip
Results: 151-180 of 537

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