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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)
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,149
Suite
$8,699
From
US$6,149
Save 6,149
Per Person
View Trip
15 Day Yacht Harbors & Southern Island Discovery with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 08 January 2028
Visit: Barbados, Saint Lucia, Curacao, Aruba (+6 more), Bonaire, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Saint Martin
Inside
-
Oceanview
-
Balcony
$7,829
Suite
$12,959
From
US$7,829
Per Person
View Trip
9 Day A Journey Of Tranquil Tropical Beauty & Rainforest Adventures with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 January 2027
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,640
From
US$5,640
Per Person
View Trip
14 Day Discover the Vibes of the Caribbean with Emerald Cruises
New ReleaseCruise

14 Days (13 Nights) Miami to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Visit: USA, Bahamas, Turks and Caicos Islands, Puerto Rico (+4 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Inside
-
Oceanview
-
Balcony
-
Suite
$13,945
From
US$13,945
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,599
Suite
$7,899
From
US$5,599
Save 5,599
Per Person
View Trip
8 Day A Journey Through Island Charm & Cultural Treasures with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visit: USA, Turks and Caicos Islands, Saint Barthelemy, Antigua and Barbuda, Anguilla, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
11 Day Island Odyssey: Bahamas to the Grenadine with Scenic
New ReleaseCruise

11 Days (10 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse I
Departure: 10 October 2027
Visit: Bahamas, Turks and Caicos Islands, Virgin Islands, Saint Barthelemy, Martinique, Saint Vincent, Barbados
Select Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,358
Suite
$11,495
From
US$9,358
Save 437
Per Person
View Trip
16 Day An Extended Journey into Island Bliss & Lively Celebrations with Explora Journeys
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Saint Barthelemy, Anguilla, USA, Dominican Republic
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$11,390
From
US$11,390
Per Person
View Trip
8 Day Cruising the Leeward Islands with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Philipsburg to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Apr 2028
Visit: Sint Maarten, Saint Kitts and Nevis, Anguilla, Virgin Islands, Saint Barthelemy
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$5,815
Balcony
-
Suite
$7,390
From
US$5,815
Save 620
Per Person
View Trip
19 Day Bridgetown to Bridgetown with Silversea
Cruise

19 Days (18 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 29 February 2028
Visit: Barbados, Saint Vincent, Grenada, Curacao (+10 more), Aruba, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Lucia, Guadeloupe, Saint Martin, Virgin Islands, Saint Kitts and Nevis, Dominica
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$8,100
Suite
$7,400
From
US$7,400
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$3,745
From
US$3,745
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
$11,799
Suite
$12,199
From
US$11,799
Save 11,799
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
Inside
-
Oceanview
$8,100
Balcony
$8,900
Suite
$8,400
From
US$8,100
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: 04 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Martinique, Grenada, Bonaire, Curacao, Aruba
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
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: 20 December 2026
Visit: Puerto Rico, Virgin Islands, Montserrat, Saint Lucia, Martinique
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,200
Balcony
$4,900
Suite
$8,600
From
US$4,200
Save 1,500
Per Person
View Trip
11 Day Rainforest To Reef with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 18 November 2027
Visit: USA, Bahamas, Mexico, Belize, Honduras, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,599
Suite
$9,749
From
US$8,599
Save 8,599
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: 29 February 2028
Visit: Barbados, Saint Vincent, Grenada, Curacao (+5 more), Aruba, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Lucia
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,100
Balcony
$5,800
Suite
$5,300
From
US$5,100
Save 1,500
Per Person
View Trip
11 Day Tropical Heart & Soul with Regent Seven Seas
Cruise

11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 25 January 2028
Visit: Barbados, Saint Vincent, Saint Lucia, Martinique (+5 more), Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,899
Suite
$10,099
From
US$8,899
Save 8,899
Per Person
View Trip
8 Day A Journey of Thrilling Island Adventures & Historical Wonders with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Nov 2027 to Feb 2028
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
8 Day A Journey Through the Vibrant Pulse of the Antilles with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 29 January 2028
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
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: 06 February 2027
Visit: USA, Puerto Rico, Virgin Islands, Aruba (+5 more), Curacao, Bonaire, Grenada, Saint Lucia, Barbados
All-Inclusive Fare
Inside
-
Oceanview
$8,300
Balcony
$9,100
Suite
$8,600
From
US$8,300
Per Person
View Trip
11 Day Tropical Island Havens with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departures: Dec 2026 to Mar 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy, 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 4,599
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
Yours to Explore
Inside
-
Oceanview
-
Balcony
$7,999
Suite
$14,399
From
US$7,999
Per Person
View Trip
8 Day Vibes of the Virgin Islands with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Saint Thomas to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Dec 2026 to Mar 2027
Visit: Virgin Islands, Anguilla, Saint Martin, Saint Barthelemy
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$4,778
Balcony
-
Suite
$6,177
From
US$4,778
Save 1,103
Per Person
View Trip
15 Day Caribbean Celebration with Regent Seven Seas
Cruise

15 Days (14 Nights) Tampa to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 21 December 2026
Visit: USA, Cayman Islands, Jamaica, Aruba (+5 more), Curacao, Bonaire, Saint Kitts and Nevis, Saint Martin, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,699
Suite
$13,799
From
US$12,699
Save 12,699
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 Dawn
Departure: 03 March 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,800
Balcony
$5,400
Suite
$10,500
From
US$4,800
Save 1,500
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: 15 January 2027
Visit: Barbados, Saint Vincent, Grenada, Aruba (+4 more), Curacao, Bonaire, Martinique, Saint Lucia
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$5,900
Balcony
$6,600
Suite
$6,100
From
US$5,900
Save 1,500
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: 17 December 2027
Visit: Barbados, Saint Lucia, Saint Vincent, Grenada (+5 more), Curacao, Bonaire, Aruba, Saint Kitts and Nevis, Martinique
All-Inclusive Fare
Inside
-
Oceanview
$9,200
Balcony
$10,200
Suite
$9,600
From
US$9,200
Per Person
View Trip
15 Day Caribbean Yacht Explorer with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 11 March 2028
Visit: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Virgin Islands, Saint Martin, Martinique, Saint Vincent, Grenada
Inside
-
Oceanview
-
Balcony
$7,829
Suite
$12,959
From
US$7,829
Per Person
View Trip
12 Day Yachtsman's Holiday In Aruba, Bonaire & Curacao with Seabourn
Cruise

12 Days (11 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 28 December 2027
Visit: Saint Martin, Virgin Islands, Anguilla, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Guadeloupe, Aruba, Curacao, Bonaire, Barbados
Inside
-
Oceanview
-
Balcony
$5,849
Suite
$10,799
From
US$5,849
Per Person
View Trip
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