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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)
17 Day An Extended Journey Through Ancient Marvels & Glittering Shores with Explora Journeys
Cruise

17 Days (16 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 January 2027
Visit: USA, Jamaica, Guatemala, Honduras (+6 more), Belize, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,000
Suite
$7,910
From
US$7,000
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 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
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
15 Day An Extended Journey of Tropical Harmony & Natural Wonders with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands (+4 more), Dominican Republic, USA, Guadeloupe, Saint Martin
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,600
Suite
$7,575
From
US$6,600
Per Person
View Trip
12 Day Caribbean Island Tapestry with Oceania Cruises
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 19 February 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,466
Suite
$7,697
From
US$5,466
Save 5,732
Per Person
View Trip
11 Day Miami to Miami with Silversea
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 30 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,560
Balcony
$5,440
Suite
$8,600
From
US$4,560
Save 1,140
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 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
14 Day Bountiful Caribbean with Oceania Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 07 January 2027
Visit: USA, Cayman Islands, Jamaica, Aruba (+4 more), Curacao, Grenada, Guadeloupe, Virgin Islands
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,559
Suite
$7,790
From
US$5,559
Save 5,839
Per Person
View Trip
8 Day A Journey Of Sun-hazed Island Enchantment & Caribbean Treasures with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 January 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Turks and Caicos Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,130
Suite
$4,760
From
US$4,130
Per Person
View Trip
13 Day Bridgetown to Miami with Silversea
Cruise

13 Days (12 Nights) Bridgetown to Miami
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 25 January 2027
Visit: Barbados, Saint Vincent, Grenada, Bonaire (+5 more), Curacao, Aruba, Virgin Islands, Puerto Rico, USA
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,830
Balcony
$5,530
Suite
$5,250
From
US$4,830
Save 2,070
Per Person
View Trip
11 Day A Journey Of Caribbean Charm & Spectacular Natural Beauty with Explora Journeys
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ships: Explora II, Explora I
Departures: Nov 2026 to Nov 2027
Visit: USA, Curacao, Aruba, Colombia, Cayman Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,215
Suite
$5,880
From
US$5,215
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
Cruise

8 Days (7 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Sakara, Emerald Azzurra
Departures: Jan 2026 to Mar 2027
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+4 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$3,272
Balcony
-
Suite
$4,805
From
US$3,272
Save 18,011
Per Person
View Trip
11 Day Bridgetown to Bridgetown with Silversea
Cruise

11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 18 February 2027
Visit: Barbados, Saint Vincent, Grenada, Bonaire (+4 more), Curacao, Saint Kitts and Nevis, Martinique, Saint Lucia
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,720
Balcony
$5,280
Suite
$4,800
From
US$4,720
Save 1,180
Per Person
View Trip
15 Day Carnival Of Caribbean Colors with Regent Seven Seas
Cruise

15 Days (14 Nights) Panama City to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 31 March 2027
Visit: Panama, Colombia, Aruba, Curacao (+6 more), Bonaire, Grenada, Saint Lucia, Saint Barthelemy, Virgin Islands, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,199
Suite
$9,689
From
US$9,199
Save 16,499
Per Person
View Trip
8 Day A Journey Of Caribbean Delicacies & Idyllic Islands with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 04 January 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,340
From
US$3,850
Per Person
View Trip
11 Day Sweetheart Sojourn with Regent Seven Seas
Cruise

11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 04 February 2028
Visit: Barbados, Grenada, Aruba, Curacao (+4 more), Bonaire, Saint Kitts and Nevis, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,799
Suite
$6,828
From
US$5,799
Save 11,999
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
13 Day Flavors Of Cartagena with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Panama City
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 02 March 2028
Visit: USA, Cayman Islands, Jamaica, Dominican Republic, Colombia, Costa Rica, Panama
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,655
Suite
$9,047
From
US$8,655
Save 14,943
Per Person
View Trip
8 Day A Journey Of Caribbean Adventure & Shimmering Tropical Harmony with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ships: Explora III, Explora I
Departures: Oct 2026 to Dec 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,570
Suite
$4,025
From
US$3,570
Per Person
View Trip
22 Day Epic Voyage: Sint Maarten to Barbados with Emerald Cruises
New ReleaseCruise

22 Days (21 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 05 February 2028
Visit: Saint Martin, Saint Kitts and Nevis, Anguilla, Virgin Islands (+7 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados, Saint Vincent, Grenada
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$17,473
Balcony
-
Suite
$22,565
From
US$17,473
Save 18,497
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
10 Day Island Indulgence with Regent Seven Seas
Cruise

10 Days (9 Nights) Bridgetown to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 February 2028
Visit: Barbados, Saint Lucia, Martinique, Dominica (+4 more), Guadeloupe, Saint Barthelemy, Saint Martin, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,797
Suite
$6,385
From
US$5,797
Save 11,001
Per Person
View Trip
17 Day An Extended Journey of Island Energy & Ocean Tranquillity with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visit: Puerto Rico, Saint Martin, Guadeloupe, Grenada (+7 more), Saint Lucia, Dominican Republic, USA, Virgin Islands, Anguilla, Martinique, Saint Kitts and Nevis
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,700
Suite
$8,960
From
US$7,700
Per Person
View Trip
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise

15 Days (14 Nights) Bridgetown to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Jan 2028 to Feb 2028
Visit: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+5 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Saint Martin
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,660
Balcony
-
Suite
$15,055
From
US$11,660
Save 12,320
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,440
Suite
$7,480
From
US$6,440
Per Person
View Trip
11 Day Caribbean Enchantment: Roundtrip Antigua with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Saint John's to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 01 March 2028
Visit: Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados, Saint Vincent, Martinique, Saint Barthelemy
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,958
Balcony
-
Suite
$9,480
From
US$6,958
Save 9,332
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,996
Suite
$8,054
From
US$5,996
Save 11,602
Per Person
View Trip
15 Day An Extended Journey from Vibrant Shores to Spectacular Scenery with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 March 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+4 more), Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,420
Suite
$8,540
From
US$7,420
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,745
Suite
$5,545
From
US$4,745
Per Person
View Trip
Results: 331-360 of 537

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