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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)
15 Day Caribbean Enchantment with Oceania Cruises
Cruise

15 Days (14 Nights) New York to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 28 October 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+4 more), Saint Lucia, Grenada, Curacao, Aruba
Your World Inclusions
Upgrade Your Experience
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,884
Suite
$8,037
From
US$4,884
Save 5,114
Per Person
View Trip
15 Day An Extended Journey Through Azure Horizons & Elegant Isles with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 February 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+5 more), Puerto Rico, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Turks and Caicos Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,520
Suite
$8,640
From
US$7,520
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
Departures: Dec 2026 to Mar 2027
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique, Saint Vincent, Grenada, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,010
Suite
$7,095
From
US$4,010
Save 89
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
13 Day Miami to Miami with Silversea
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 18 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Montserrat, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,800
Balcony
$5,760
Suite
$11,480
From
US$4,800
Save 1,200
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 Through The Caribbean's Rich History & Palm-shaded Paradise with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Dominican Republic, USA, Bahamas
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
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: 10 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda (+7 more), Montserrat, Guadeloupe, Saint Kitts and Nevis, Martinique, Saint Lucia, Grenada, Barbados
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,280
Balcony
$6,240
Suite
$9,500
From
US$5,280
Save 1,320
Per Person
View Trip
8 Day Bridgetown to Philipsburg with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 12 February 2026
Visit: Barbados, Martinique, Saint Vincent, Dominica (+4 more), Saint Barthelemy, Virgin Islands, Antigua and Barbuda, Saint Martin
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$8,400
Suite
-
From
US$8,400
Per Person
View Trip
15 Day Exotic Caribbean In Depth with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 28 November 2026
Visit: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Virgin Islands, Saint Martin, Martinique, Saint Vincent, Grenada
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,606
Suite
$12,771
From
US$7,606
Save 128
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
8 Day A Journey Across the Caribbean’s Colourful Heart with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 13 November 2027
Visit: Puerto Rico, Virgin Islands, Dominican Republic, USA, Bahamas
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
11 Day Blissful Bvi with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 05 April 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,391
Suite
$7,665
From
US$6,391
Save 12,007
Per Person
View Trip
11 Day Caribbean Splendor with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 02 February 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,977
Suite
$7,014
From
US$4,977
Save 5,221
Per Person
View Trip
10 Day A Journey Through Sacred Cenotes & Hidden Mayan Pyramids with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 06 January 2028
Visit: USA, Mexico, Guatemala, Belize, Bahamas
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,355
Suite
$6,230
From
US$5,355
Per Person
View Trip
8 Day A Journey Through Iconic Caribbean Islands & Underwater Wonders with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Feb 2028 to Mar 2028
Visit: USA, Turks and Caicos Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
12 Day Crescent Beaches & Colorful Towns with Regent Seven Seas
Cruise

12 Days (11 Nights) Panama City to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 22 February 2027
Visit: Panama, Costa Rica, Honduras, Belize (+5 more), Guatemala, Mexico, Cayman Islands, Jamaica, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$8,605
From
US$8,605
Save 14,893
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Dec 2027 to Apr 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+4 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$4,607
Balcony
-
Suite
$6,305
From
US$4,607
Save 7,140
Per Person
View Trip
21 Day Cultural Currents with Regent Seven Seas
Cruise

21 Days (20 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 26 March 2027
Visit: USA, Bahamas, Mexico, Belize (+7 more), Honduras, Jamaica, Cayman Islands, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,196
Suite
$14,450
From
US$12,196
Save 23,802
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: 16 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Guadeloupe
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,480
Suite
$8,990
From
US$6,480
Save 1,620
Per Person
View Trip
8 Day Reverie Under Sail in the Heart of the Lesser Antilles with Ponant
Cruise

8 Days (7 Nights) Marigot to Philipsburg
Cruise Line: Ponant
Ship: Le Ponant
Departure: 14 March 2026
Visit: Saint Martin, Anguilla, Virgin Islands
Inside
-
Oceanview
$9,870
Balcony
-
Suite
-
From
US$9,870
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
9 Day A Journey of Endless Sophistication and Island Charm with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 18 March 2026
Visit: USA, Virgin Islands, Guadeloupe, Barbados, Martinique, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,230
Suite
$4,770
From
US$4,230
Per Person
View Trip
9 Day Splendours of the Caribbean with Scenic
New ReleaseCruise

9 Days (8 Nights) Saint John's to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse II
Departure: 15 October 2027
Visit: Antigua and Barbuda, Saint Barthelemy, Virgin Islands, Montserrat (+5 more), Martinique, Saint Lucia, Saint Vincent, Trinidad and Tobago, Barbados
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,917
Suite
$8,208
From
US$7,917
Save 11,473
Per Person
View Trip
18 Day Bermuda & Eastern Caribbean Cruise: Sint Maarten, Antigua & Tobago with Azamara Cruises
Cruise
 (4)

18 Days (17 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$3,940
Oceanview
$4,619
Balcony
$5,774
Suite
$9,237
From
US$3,940
Save 79
Per Person
View Trip
17 Day Caribbean Cruise: New York, Bermuda & Barbados with Azamara Cruises
Cruise
 (3)

17 Days (16 Nights) New York to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 29 October 2026
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+7 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$3,206
Oceanview
$3,565
Balcony
$4,458
Suite
$7,290
From
US$3,206
Save 63
Per Person
View Trip
8 Day Caribbean escapade with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Visit: USA, Bahamas, Turks and Caicos Islands, Puerto Rico
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,649
From
US$5,649
Save 8,041
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,489
Oceanview
$2,059
Balcony
$2,499
Suite
$4,342
From
US$1,489
Per Person
View Trip
25 Day Bermuda & Eastern Caribbean Cruise: Tortola, Barbados & Saint Kitts with Azamara Cruises
Cruise
 (4)

25 Days (24 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 28 October 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands (+10 more), Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Azamara Always Included
Exclusive Savings
Inside
$5,711
Oceanview
$6,895
Balcony
$8,524
Suite
$13,549
From
US$5,711
Save 118
Per Person
View Trip
15 Day Emerald East Coast with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to New York
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 09 April 2027
Visit: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Saint Lucia, Saint Barthelemy, Puerto Rico, Bermuda
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,119
Suite
$10,609
From
US$10,119
Save 17,479
Per Person
View Trip
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