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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)
11 Day Bridgetown to San Juan with Silversea
Cruise

11 Days (10 Nights) Bridgetown to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 16 February 2027
Visit: Barbados, Saint Vincent, Grenada, Saint Lucia (+7 more), Martinique, Dominica, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Puerto Rico
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,700
Balcony
$6,500
Suite
$10,400
From
US$5,700
Save 1,500
Per Person
View Trip
8 Day Classic Caribbean Yacht Harbors with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 28 November 2026
Visit: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Saint Martin
Yours to Explore
Inside
-
Oceanview
-
Balcony
$4,499
Suite
$7,999
From
US$4,499
Per Person
View Trip
8 Day A Journey Through Balmy Shores & Stirring Scenery with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 April 2027
Visit: Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,085
From
US$4,085
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
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
11 Day Tropical Coves with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 01 March 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,099
Suite
$7,199
From
US$5,099
Save 5,099
Per Person
View Trip
8 Day Quintessential Caribbean with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Antigua and Barbuda, Saint Barthelemy
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$5,288
Balcony
-
Suite
$6,687
From
US$5,288
Save 1,103
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 Vista
Departures: Dec 2026 to Dec 2026
Visit: USA, Mexico, Honduras, Belize
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,550
Suite
$3,612
From
US$2,550
Save 3,793
Per Person
View Trip
8 Day Yacht Harbors Of Bonaire & Curacao with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 11 December 2027
Visit: Barbados, Saint Lucia, Trinidad and Tobago, Curacao, Bonaire
Inside
-
Oceanview
-
Balcony
$3,599
Suite
$7,199
From
US$3,599
Per Person
View Trip
16 Day Romance Of Roseau with Regent Seven Seas
Cruise

16 Days (15 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 16 February 2028
Visit: USA, Virgin Islands, Dominica, Saint Lucia (+6 more), Barbados, Grenada, Bonaire, Curacao, Aruba, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$15,299
Suite
$15,699
From
US$15,299
Save 15,299
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
$7,849
Suite
$8,049
From
US$7,849
Save 7,849
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
$9,499
Suite
$10,399
From
US$9,499
Save 9,499
Per Person
View Trip
8 Day Caribbean Gems with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 12 December 2026
Visit: Barbados, Saint Kitts and Nevis, Guadeloupe, Martinique, Dominica, Saint Lucia
Yours to Explore
Inside
-
Oceanview
-
Balcony
$3,799
Suite
$7,999
From
US$3,799
Per Person
View Trip
8 Day Classic Caribbean Yacht Harbors with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: Dec 2026 to Feb 2028
Visit: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Saint Martin
Yours to Explore
Inside
-
Oceanview
-
Balcony
$3,599
Suite
$7,199
From
US$3,599
Per Person
View Trip
8 Day A Journey of Intimate Island Bliss & Caribbean Breeze with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 February 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,899
Suite
$6,199
From
US$3,899
Save 3,899
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 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 Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,300
Balcony
$4,900
Suite
$9,500
From
US$4,300
Save 1,500
Per Person
View Trip
11 Day Lesser Antilles Journey with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 19 December 2026
Visit: USA, Virgin Islands, Dominica, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,149
Suite
$11,849
From
US$11,149
Save 11,149
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$11,720
From
US$11,720
Per Person
View Trip
11 Day Island Rendezvous with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 28 November 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Martin, Saint Barthelemy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,699
Suite
$9,799
From
US$8,699
Save 8,699
Per Person
View Trip
8 Day A Journey Through Captivating Caribbean Culture & Sunlit Shores with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 12 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Guadeloupe, Dominican Republic, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,425
From
US$4,425
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
$13,149
Suite
$13,649
From
US$13,149
Save 13,149
Per Person
View Trip
18 Day Tropical Serenade with Oceania Cruises
Cruise

18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 21 December 2026
Visit: USA, Mexico, Honduras, Belize (+4 more), Virgin Islands, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,949
Suite
$12,349
From
US$8,949
Save 8,949
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: 28 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Kitts and Nevis
All-Inclusive Fare
Inside
-
Oceanview
$5,600
Balcony
$6,100
Suite
$10,700
From
US$5,600
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
Inside
-
Oceanview
$5,300
Balcony
$5,600
Suite
$5,400
From
US$5,300
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: 06 February 2027
Visit: Guadeloupe, Antigua and Barbuda, Saint Barthelemy, Saint Kitts and Nevis, Anguilla, Saint Martin
Inside
-
Oceanview
$8,770
Balcony
$12,440
Suite
$13,390
From
US$8,770
Per Person
View Trip
12 Day San Juan to San Juan with Silversea
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 25 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Saint Vincent, Grenada, Curacao, Bonaire
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,200
Balcony
$5,900
Suite
$11,500
From
US$5,200
Save 1,500
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) Saint Thomas to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 03 January 2027
Visit: Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,765
From
US$5,765
Save 940
Per Person
View Trip
9 Day A Journey Through Mayan Marvels, Rich Reefs & Ocean Serenity with Explora Journeys
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 17 November 2026
Visit: USA, Mexico, Honduras, Belize, Bahamas
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,620
From
US$4,620
Per Person
View Trip
17 Day An Extended Journey through Enchanting Islands & Lush Landscapes with Explora Journeys
Cruise

17 Days (16 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 January 2027
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda (+7 more), Saint Kitts and Nevis, Puerto Rico, Saint Martin, Guadeloupe, Grenada, Saint Lucia, Dominican Republic
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$10,080
From
US$10,080
Per Person
View Trip
Results: 331-360 of 507

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