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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 539 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 702 departures starting between January 2026 and April 2028.
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539 Cruises (702 Cruise Departures)
19 Day An Extended Journey Through Caribbean Beauty & Ocean Stillness with Explora Journeys
Cruise

19 Days (18 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 17 November 2026
Visit: USA, Mexico, Honduras, Belize (+5 more), Bahamas, Curacao, Aruba, Colombia, Cayman Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$8,810
Suite
$9,975
From
US$8,810
Per Person
View Trip
8 Day Cruising the Leeward Islands with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Marigot to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara, Emerald Azzurra
Departures: Feb 2026 to Apr 2027
Visit: Saint Martin, Anguilla, Virgin Islands, Bonaire, Saint Barthelemy
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$3,691
Balcony
-
Suite
$5,291
From
US$3,691
Save 18,047
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: 21 February 2026
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique, Saint Vincent, Grenada, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$11,607
From
US$11,607
Save 224
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
$4,486
From
US$3,031
Save 3,167
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,690
Suite
$5,460
From
US$4,690
Per Person
View Trip
12 Day Waterfalls & Divers with Regent Seven Seas
Cruise

12 Days (11 Nights) Galveston to Galveston
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 30 November 2026
Visit: USA, Cayman Islands, Honduras, Belize, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,390
Suite
$7,615
From
US$6,390
Save 12,608
Per Person
View Trip
9 Day A Journey Of Tranquil Tropical Beauty & Rainforest Adventures with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 January 2027
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,690
Suite
$5,460
From
US$4,690
Per Person
View Trip
8 Day Bridgetown to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 28 February 2027
Visit: Barbados, Saint Lucia, Saint Barthelemy, Virgin Islands, Antigua and Barbuda, Dominica, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,000
Balcony
$4,480
Suite
$4,080
From
US$4,000
Save 1,000
Per Person
View Trip
9 Day A Journey Of Latin Flair, Natural Beauty & Vibrant History with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 12 February 2026
Visit: USA, Dominican Republic, Dominica, Barbados, Guadeloupe, Virgin Islands, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,575
Suite
$6,450
From
US$4,575
Per Person
View Trip
8 Day Bridgetown to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 12 December 2026
Visit: Barbados, Saint Lucia, Martinique, Guadeloupe, Antigua and Barbuda, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,010
Balcony
$3,360
Suite
$3,150
From
US$3,010
Save 1,290
Per Person
View Trip
8 Day A Journey Of Caribbean Celebrations & Island Wonders with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Saint Barthelemy, Anguilla, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,720
Suite
$5,320
From
US$4,720
Per Person
View Trip
16 Day An Extended Journey from Sophisticated Harbours to Sun-Soaked Horizons with Explora Journeys
Cruise

16 Days (15 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 14 March 2027
Visit: USA, Turks and Caicos Islands, Antigua and Barbuda, Dominica (+7 more), Saint Vincent, Barbados, Grenada, Saint Lucia, Martinique, Saint Barthelemy, Virgin Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$8,060
Suite
$9,335
From
US$8,060
Per Person
View Trip
8 Day Philipsburg to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 26 February 2026
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Grenada, Martinique, Saint Vincent, Barbados
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$6,700
Suite
-
From
US$6,700
Per Person
View Trip
10 Day Alluring Antilles with Oceania Cruises
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 27 January 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Kitts and Nevis
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,709
Suite
$5,358
From
US$3,709
Save 3,889
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
11 Day Bridgetown to Fort Lauderdale with Silversea
Cruise

11 Days (10 Nights) Bridgetown to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 02 February 2026
Visit: Barbados, Saint Vincent, Saint Lucia, Dominica (+4 more), Guadeloupe, Saint Kitts and Nevis, Virgin Islands, USA
All-Inclusive Fare
Inside
-
Oceanview
$7,000
Balcony
-
Suite
$8,640
From
US$7,000
Per Person
View Trip
22 Day San Juan to San Juan with Silversea
Cruise

22 Days (21 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+8 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda, Dominica, Curacao, Bonaire
All-Inclusive Fare
Inside
-
Oceanview
$8,100
Balcony
$9,300
Suite
$17,000
From
US$8,100
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
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
12 Day Miami to Miami with Silversea
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 27 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Guadeloupe
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,240
Suite
$9,380
From
US$6,240
Save 1,560
Per Person
View Trip
8 Day A Journey Through Beguiling Caribbean Coastlines & Lush Landscapes with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 08 November 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Virgin Islands, Saint Barthelemy, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,400
Suite
$5,080
From
US$4,400
Per Person
View Trip
8 Day A Journey From San Juan To Miami with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 February 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy, Anguilla, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,605
Suite
$8,645
From
US$5,605
Per Person
View Trip
15 Day Dutchman's Caribbean with Oceania Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 11 November 2026
Visit: USA, Cayman Islands, Jamaica, Aruba (+5 more), Curacao, Grenada, Barbados, Saint Lucia, Saint Kitts and Nevis
Your World Inclusions
Upgrade Your Experience
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,882
Suite
$7,841
From
US$4,882
Save 5,116
Per Person
View Trip
13 Day Mesoamerican Majesty with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 28 January 2026
Visit: USA, Mexico, Honduras, Guatemala, Belize, Jamaica, Cayman Islands
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,609
Suite
$8,228
From
US$5,609
Save 5,889
Per Person
View Trip
18 Day Tropical Triumph with Oceania Cruises
Cruise

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 01 March 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands (+5 more), Saint Kitts and Nevis, Antigua and Barbuda, Mexico, Honduras, Belize
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,110
Suite
$11,311
From
US$8,110
Save 8,488
Per Person
View Trip
11 Day San Juan to Bridgetown with Silversea
Cruise

11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 06 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+7 more), Montserrat, Guadeloupe, Dominica, Martinique, Saint Lucia, Grenada, Barbados
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,960
Balcony
$5,920
Suite
$8,900
From
US$4,960
Save 1,240
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,920
Balcony
$4,620
Suite
$9,660
From
US$3,920
Save 1,680
Per Person
View Trip
9 Day A Journey Of Tropical Festivities & Dazzling Island Beauty with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 20 December 2026
Visit: USA, Jamaica, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,720
Suite
$6,640
From
US$5,720
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
10 Day Vibrant Island Culture with Regent Seven Seas
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 27 January 2028
Visit: USA, Saint Barthelemy, Saint Kitts and Nevis, Saint Lucia, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,973
Suite
$7,365
From
US$6,973
Save 12,225
Per Person
View Trip
Results: 361-390 of 539

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