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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)
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
Inside
-
Oceanview
-
Balcony
-
Suite
$5,020
From
US$5,020
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
Departures: Apr 2026 to Apr 2027
Visit: Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Inside
-
Oceanview
$8,770
Balcony
$12,440
Suite
$13,390
From
US$8,770
Per Person
View Trip
13 Day Calypsco Currents with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 20 March 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+4 more), Dominica, Guadeloupe, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,599
Suite
$11,599
From
US$10,599
Save 10,599
Per Person
View Trip
9 Day Southern Caribbean Gems with Seabourn
Cruise

9 Days (8 Nights) Miami to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 20 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Saint Vincent, Barbados
Yours to Explore
Inside
-
Oceanview
-
Balcony
$3,799
Suite
$7,999
From
US$3,799
Per Person
View Trip
18 Day A Grand Journey Through Balmy Shores & Enchanting Nature to Panama’s Wonders with Explora Journeys
Cruise

18 Days (17 Nights) San Juan to Panama City
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 April 2027
Visit: Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis (+6 more), USA, Jamaica, Curacao, Aruba, Colombia, Panama
Inside
-
Oceanview
-
Balcony
-
Suite
$9,415
From
US$9,415
Per Person
View Trip
21 Day Sju To Mia with Oceania Cruises
Cruise

21 Days (20 Nights) San Juan to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 19 February 2027
Visit: Puerto Rico, Saint Barthelemy, Saint Martin, Saint Kitts and Nevis (+10 more), Antigua and Barbuda, Virgin Islands, USA, Cayman Islands, Jamaica, Aruba, Curacao, Bonaire, Dominican Republic, Bahamas
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,749
Suite
$13,049
From
US$8,749
Save 8,749
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
Inside
-
Oceanview
$6,200
Balcony
$7,100
Suite
$6,600
From
US$6,200
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
Select Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,963
Suite
$9,521
From
US$7,963
Save 372
Per Person
View Trip
11 Day Caribbean Yacht Harbor Holiday with Seabourn
Cruise

11 Days (10 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 18 December 2027
Visit: Barbados, Grenada, Saint Vincent, Martinique (+6 more), Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Anguilla, Saint Martin
Inside
-
Oceanview
-
Balcony
$5,399
Suite
$9,899
From
US$5,399
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: 11 March 2028
Visit: Barbados, Saint Lucia, Guadeloupe, Saint Martin, Virgin Islands, Saint Kitts and Nevis, Dominica
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,900
Suite
$3,600
From
US$3,600
Save 1,500
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
Inside
-
Oceanview
$13,390
Balcony
-
Suite
-
From
US$13,390
Per Person
View Trip
10 Day A Journey of Palm - Shaded Elegance & Caribbean Cultural Fusion with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 04 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Barthelemy
Inside
-
Oceanview
-
Balcony
-
Suite
$4,685
From
US$4,685
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
$18,649
Suite
$20,349
From
US$18,649
Save 18,649
Per Person
View Trip
11 Day A Journey of Reggae Beats & Hypnotic Caribbean Wonders with Explora Journeys
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 13 December 2027
Visit: USA, Jamaica, Bonaire, Curacao, Aruba, Bahamas
Inside
-
Oceanview
-
Balcony
-
Suite
$5,215
From
US$5,215
Per Person
View Trip
8 Day A Journey Through Secluded Isles & Caribbean Havens with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 February 2027
Visit: USA, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,160
From
US$5,160
Per Person
View Trip
9 Day Southern Caribbean Yacht Harbors with Seabourn
Cruise

9 Days (8 Nights) Halifax to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Venture
Departures: Oct 2026 to Oct 2027
Visit: Canada, Saint Kitts and Nevis, Spain, Saint Lucia, Barbados
Yours to Explore
Inside
-
Oceanview
-
Balcony
-
Suite
$6,499
From
US$6,499
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: 26 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Montserrat
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,400
Balcony
$5,000
Suite
$8,300
From
US$4,400
Save 1,500
Per Person
View Trip
8 Day A Journey of Salsa Beats, Spectacular Fireworks & Dominican Charm with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 30 December 2027
Visit: Puerto Rico, Virgin Islands, Dominican Republic, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$5,355
From
US$5,355
Per Person
View Trip
12 Day Bridgetown to Bridgetown with Silversea
Cruise

12 Days (11 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 04 January 2027
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+5 more), Aruba, Curacao, Bonaire, Grenada, Saint Vincent
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$6,100
Balcony
$6,900
Suite
$6,500
From
US$6,100
Save 1,500
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
Inside
-
Oceanview
$6,200
Balcony
$7,100
Suite
$12,700
From
US$6,200
Per Person
View Trip
15 Day An Extended Journey Through Islands of Scenic Wonder & Coastal History with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 06 December 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+5 more), Saint Barthelemy, Puerto Rico, Anguilla, Saint Kitts and Nevis, Turks and Caicos Islands
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,720
From
US$6,720
Per Person
View Trip
6 Day Beaches of the Virgin Islands with Emerald Cruises
New ReleaseCruise

6 Days (5 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Jan 2028 to Feb 2028
Visit: Puerto Rico, Virgin Islands
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$4,638
Balcony
-
Suite
$5,808
From
US$4,638
Save 457
Per Person
View Trip
12 Day Cupid In The Caribbean with Regent Seven Seas
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 05 February 2028
Visit: USA, Mexico, Guatemala, Belize, Honduras, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,799
Suite
$12,199
From
US$11,799
Save 11,799
Per Person
View Trip
11 Day Tropical Passage with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 20 March 2027
Visit: USA, Virgin Islands, Dominica, Barbados (+4 more), Saint Lucia, Martinique, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,099
Suite
$10,449
From
US$10,099
Save 10,099
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
Departures: Jan 2028 to Jan 2028
Visit: Barbados, Saint Vincent, Martinique, Saint Barthelemy, Dominica, Grenada, Saint Lucia
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,100
Balcony
$4,600
Suite
$4,300
From
US$4,100
Save 1,500
Per Person
View Trip
8 Day A Journey Of Blissful Escapes & Island Splendour with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands, Dominican Republic, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,310
From
US$4,310
Per Person
View Trip
8 Day A Journey Through Shimmering Island History & Mesmerisingly Cultures with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 27 November 2027
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Dominican Republic, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
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: 03 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Montserrat, Saint Kitts and Nevis
All-Inclusive Fare
Inside
-
Oceanview
$5,400
Balcony
$6,100
Suite
$9,100
From
US$5,400
Per Person
View Trip
15 Day Caribbean Compass with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to New York
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 15 April 2027
Visit: USA, Aruba, Curacao, Bonaire (+4 more), Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,799
Suite
$13,799
From
US$12,799
Save 12,799
Per Person
View Trip
17 Day An Extended Journey of Sparkling Skies & Dramatic Natural Beauty with Explora Journeys
Cruise

17 Days (16 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 20 December 2026
Visit: USA, Jamaica, Dominican Republic, Virgin Islands (+4 more), Saint Martin, Puerto Rico, Antigua and Barbuda, Guadeloupe
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$12,875
From
US$12,875
Per Person
View Trip
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