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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)
8 Day Miami, Fl to Miami, Fl with Silversea
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departures: Nov 2027 to Dec 2027
Visit: USA, Bahamas, Turks and Caicos Islands
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,300
Balcony
$4,000
Suite
$6,600
From
US$3,300
Save 1,500
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$3,850
From
US$3,850
Per Person
View Trip
9 Day A Journey Through Majestic Island Paradises & Radiant Cultures with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 November 2027
Visit: USA, Turks and Caicos Islands, Saint Barthelemy, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$4,450
From
US$4,450
Per Person
View Trip
8 Day Treasures Of Aruba, Bonaire & Curacao with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: Jan 2027 to Jan 2028
Visit: Barbados, Saint Lucia, Curacao, Aruba, Bonaire
Yours to Explore
Inside
-
Oceanview
-
Balcony
$3,999
Suite
$7,199
From
US$3,999
Per Person
View Trip
8 Day Rum, Roatan & Ruins with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 16 February 2027
Visit: USA, Mexico, Belize, Honduras
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,949
Suite
$8,199
From
US$7,949
Save 7,949
Per Person
View Trip
8 Day A Journey Into Caribbean Exploration & Island Delights with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 01 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,400
From
US$4,400
Per Person
View Trip
8 Day A Journey From Glorious Shorelines To Nature's Allure with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 February 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$4,425
From
US$4,425
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$3,850
From
US$3,850
Per Person
View Trip
17 Day An Extended Journey of Pearl-Blue Horizons & Maritime Grace with Explora Journeys
Cruise

17 Days (16 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 19 February 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Anguilla, Antigua and Barbuda, Guadeloupe
Inside
-
Oceanview
-
Balcony
-
Suite
$9,150
From
US$9,150
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 Shadow
Departure: 24 December 2027
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Virgin Islands, Turks and Caicos Islands
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,500
Balcony
$6,700
Suite
$11,100
From
US$5,500
Save 1,500
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: 05 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,400
Suite
$9,800
From
US$7,400
Save 2,500
Per Person
View Trip
8 Day History and Culture Visiting Caribbean Jewels with Ponant
Cruise

8 Days (7 Nights) Marigot to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departures: Dec 2026 to Mar 2027
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe
Inside
-
Oceanview
$8,220
Balcony
$11,650
Suite
$12,530
From
US$8,220
Per Person
View Trip
14 Day Caribbean Calm with Oceania Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 06 December 2027
Visit: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Barbados, Saint Lucia, Guadeloupe, Virgin Islands
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,699
Suite
$8,999
From
US$6,699
Save 6,699
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl 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, Anguilla
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,500
Suite
$11,000
From
US$7,500
Save 1,500
Per Person
View Trip
15 Day An Extended Journey of Sunlit Horizons & Sapphire Bays with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 22 November 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+5 more), Saint Martin, Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Turks and Caicos Islands
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,140
From
US$7,140
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: 11 December 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$7,300
Suite
$9,700
From
US$7,300
Per Person
View Trip
9 Day San Juan to Miami, Fl with Silversea
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, USA
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,900
Suite
$9,800
From
US$5,900
Save 1,500
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,299
Suite
$11,599
From
US$8,299
Save 8,299
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
$9,599
Suite
$9,999
From
US$9,599
Save 9,599
Per Person
View Trip
11 Day Caribbean Mystique with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 30 March 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+5 more), Saint Barthelemy, Saint Martin, Dominican Republic, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$10,099
Suite
$10,499
From
US$10,099
Save 10,099
Per Person
View Trip
16 Day An Extended Journey Through Wild Beauty and Tropical Festivities with Explora Journeys
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 December 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis (+6 more), Turks and Caicos Islands, USA, Jamaica, Dominican Republic, Virgin Islands, Saint Martin
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$9,225
From
US$9,225
Per Person
View Trip
22 Day Bonaire, Curacao & Southern Caribbean Holiday with Seabourn
Cruise

22 Days (21 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 18 December 2027
Visit: Barbados, Grenada, Saint Vincent, Martinique (+9 more), Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Anguilla, Saint Martin, Aruba, Curacao, Bonaire
Inside
-
Oceanview
-
Balcony
$10,169
Suite
$18,629
From
US$10,169
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
Inside
-
Oceanview
$20,135
Balcony
-
Suite
-
From
US$20,135
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,200
From
US$7,200
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
$10,099
Suite
$10,999
From
US$10,099
Save 10,099
Per Person
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
Cruise

15 Days (14 Nights) Saint John's to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Jan 2028 to Mar 2028
Visit: Antigua and Barbuda, Saint Kitts and Nevis, Guadeloupe, Saint Barthelemy (+4 more), Virgin Islands, Puerto Rico, Sint Maarten, Montserrat
Inside
-
Oceanview
$14,090
Balcony
-
Suite
-
From
US$14,090
Per Person
View Trip
15 Day An Extended Journey Through Golden Shores & Island Grace with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy (+4 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Guadeloupe
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,140
From
US$7,140
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 Shadow
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Saint Vincent
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,600
Balcony
$5,300
Suite
$9,600
From
US$4,600
Save 2,500
Per Person
View Trip
8 Day Yachtsman's Harbors with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 05 February 2027
Visit: USA, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,949
Suite
$4,899
From
US$2,949
Save 2,949
Per Person
View Trip
15 Day An Extended Journey from Ocean Calm to Vibrant Culture with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 07 March 2027
Visit: Puerto Rico, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis (+6 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Dominica, Saint Vincent, Barbados
Inside
-
Oceanview
-
Balcony
-
Suite
$7,950
From
US$7,950
Per Person
View Trip
Results: 271-300 of 507

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