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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 522 unique cruise itineraries with 844 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)
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,520
Balcony
$4,320
Suite
$8,500
From
US$3,520
Save 880
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 Fare
Exclusive Savings
Inside
-
Oceanview
$4,240
Balcony
$4,880
Suite
$10,020
From
US$4,240
Save 1,060
Per Person
View Trip
11 Day Sunset Serenity with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Tampa
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 01 December 2026
Visit: USA, Aruba, Curacao, Bonaire, Jamaica, Cayman Islands
Upgrade Your Horizon
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,996
Suite
$8,054
From
US$5,996
Save 11,602
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: 21 December 2026
Visit: USA, Mexico, Honduras, Belize
Your World Inclusions
Upgrade Your Experience
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,031
Suite
$4,680
From
US$3,031
Save 3,167
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Sint Maarten, Barbados & Saint Kitts with Azamara Cruises
Cruise
 (8)

15 Days (14 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 30 November 2027
Visit: USA, Virgin Islands, Saint Martin, Martinique (+5 more), Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$3,523
Oceanview
$4,348
Balcony
$5,502
Suite
$8,082
From
US$3,523
Save 76
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
9 Day Beaches of the Grenadines with Emerald Cruises
New ReleaseCruise
 (3)

9 Days (8 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 11 December 2027
Visit: Barbados, Saint Lucia, Saint Vincent
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,085
Balcony
-
Suite
$7,025
From
US$5,085
Save 7,405
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: 11 February 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,000
Suite
$9,840
From
US$6,000
Save 1,500
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, Antigua & Barbados with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 21 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+9 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy
Azamara Always Included
Exclusive Savings
Inside
$3,812
Oceanview
$3,996
Balcony
$5,151
Suite
$7,993
From
US$3,812
Save 87
Per Person
View Trip
11 Day Caribbean Island Hopping: Sint Maarten to Barbados with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 12 January 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,817
Balcony
-
Suite
$9,242
From
US$6,817
Save 9,173
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (4)

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
Exclusive Savings
Inside
$3,717
Oceanview
$4,697
Balcony
$5,715
Suite
$8,693
From
US$3,717
Save 82
Per Person
View Trip
23 Day Caribbean Intensive Cruise: Sint Maarten, Barbados & Cozumel with Azamara Cruises
Cruise
 (8)

23 Days (22 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 30 November 2027
Visit: USA, Virgin Islands, Saint Martin, Martinique (+8 more), Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico, Mexico, Belize, Honduras
Azamara Always Included
Exclusive Savings
Inside
$5,618
Oceanview
$6,918
Balcony
$8,683
Suite
$12,689
From
US$5,618
Save 121
Per Person
View Trip
32 Day Loving The Island Life with Oceania Cruises
Cruise
 (1)

32 Days (31 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 21 November 2027
Visit: USA, Mexico, Honduras, Belize (+14 more), Aruba, Curacao, Bonaire, Grenada, Saint Lucia, Guadeloupe, Saint Martin, Bahamas, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$8,142
Oceanview
$8,869
Balcony
$13,380
Suite
$18,521
From
US$8,142
Save 8,456
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
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
7 Day Eastern Caribbean Cruise: St.lucia, Dominica & St.kitts with Azamara Cruises
Cruise
 (3)

7 Days (6 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 12 December 2026
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Puerto Rico
Azamara Always Included
Inside
$1,269
Oceanview
$1,629
Balcony
$2,109
Suite
$3,243
From
US$1,269
Per Person
View Trip
9 Day A Journey From San Juan To San Juan with Explora Journeys
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 03 March 2026
Visit: Puerto Rico, Grenada, Saint Vincent, Barbados, Martinique, Saint Barthelemy, Saint Kitts and Nevis
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,635
Suite
$5,220
From
US$4,635
Per Person
View Trip
10 Day Western Caribbean with Cunard
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Mar 2026 to Dec 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Mexico
Inside
$729
Oceanview
$759
Balcony
$899
Suite
$2,699
From
US$729
Per Person
View Trip
13 Day Miami to Bridgetown with Silversea
Cruise

13 Days (12 Nights) Miami to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 19 March 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy (+5 more), Curacao, Bonaire, Grenada, Saint Vincent, Barbados
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,640
Balcony
$5,360
Suite
$4,960
From
US$4,640
Save 1,160
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 Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,000
Suite
$9,900
From
US$6,000
Save 1,500
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 Inclusions
Your World Included Credit
Exclusive Savings
Inside
$2,935
Oceanview
$3,711
Balcony
$4,293
Suite
$6,039
From
US$2,935
Save 3,063
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
Your World Included Credit
Exclusive Savings
Inside
$3,043
Oceanview
$4,013
Balcony
$4,789
Suite
$6,729
From
US$3,043
Save 3,155
Per Person
View Trip
10 Day Southern Caribbean Cruise: St.barts, Antigua & Tortola with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 05 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, USA
Azamara Always Included
Exclusive Savings
Inside
$2,488
Oceanview
$3,079
Balcony
$3,681
Suite
$5,650
From
US$2,488
Save 61
Per Person
View Trip
11 Day Splendid Sunsets with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 17 February 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,032
Oceanview
$3,808
Balcony
$4,487
Suite
$6,524
From
US$3,032
Save 3,166
Per Person
View Trip
11 Day Paradise At Sea with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 07 February 2028
Visit: USA, Bahamas, Puerto Rico, Saint Kitts and Nevis (+4 more), Antigua and Barbuda, Saint Martin, Virgin Islands, Dominican Republic
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,033
Oceanview
$3,809
Balcony
$4,488
Suite
$6,525
From
US$3,033
Save 3,165
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
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
$4,118
Oceanview
$4,506
Balcony
$6,834
Suite
$9,356
From
US$4,118
Save 4,280
Per Person
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

15 Days (14 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 28 February 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Saint Barthelemy, Montserrat, Antigua and Barbuda, Guadeloupe
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$22,621
From
US$22,621
Save 659
Per Person
View Trip
9 Day Southern Caribbean Holiday Cruise: British Virgin Islands, Dominica & Grenada with Azamara Cruises
Cruise
 (4)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,189
Oceanview
$2,684
Balcony
$3,266
Suite
$4,973
From
US$2,189
Per Person
View Trip
8 Day Eastern Caribbean Cruise: Sint Maarten, Saint Kitts & Nevis with Azamara Cruises
Cruise
 (4)

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
$1,919
Oceanview
$2,363
Balcony
$2,877
Suite
$4,361
From
US$1,919
Per Person
View Trip
Results: 91-120 of 522

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