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1,860 Cruises (4,669 Cruise Departures)
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (9)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 31 January 2027
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,542
Oceanview
$1,572
Balcony
$2,582
Suite
$3,322
From
US$1,542
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departure: 16 January 2028
Visit: Puerto Rico, Aruba, Barbados, Saint Martin, Saint Kitts and Nevis
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
Per Person
View Trip
15 Day Caribbean East/West Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 15 August 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Mexico, Belize, Honduras
Princess Standard
Inside
$1,508
Oceanview
-
Balcony
$1,548
Suite
$2,338
From
US$1,508
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 28 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Inside
$1,253
Oceanview
$1,253
Balcony
$1,323
Suite
$2,863
From
US$1,253
Per Person
View Trip
8 Day Eastern Caribbean with Celebration Key Holiday with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 20 December 2026
Visit: USA, Puerto Rico, Turks and Caicos Islands, Bahamas
Princess Standard
Sanctuary Collection
Inside
$939
Oceanview
$1,079
Balcony
$1,244
Suite
$1,999
From
US$939
Per Person
View Trip
11 Day A Journey Through Amazonian Mesmerising Wonders to the Caribbean Sunlit Landscapes with Explora Journeys
Cruise
 (1)

11 Days (10 Nights) Manaus to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 17 February 2028
Visit: Brazil, Trinidad and Tobago, Saint Lucia, Dominica, Saint Martin, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$7,195
From
US$7,195
Per Person
View Trip
10 Day Antigua, St. Lucia & St. Kitts with Celebrity Cruises
Cruise
 (2)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Eclipse
Departure: 03 December 2026
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Dominica, Antigua and Barbuda
Exclusive Savings
Inside
$1,093
Oceanview
$1,345
Balcony
$1,376
Suite
$4,601
From
US$1,245
Save 504
Per Person
View Trip
22 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

22 Days (21 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departure: 24 February 2028
Visit: USA, Aruba, Bonaire, Curacao (+7 more), Dominican Republic, Jamaica, Colombia, Panama, Costa Rica, Honduras, Belize
Inside
$2,811
Oceanview
$3,121
Balcony
$3,901
Suite
-
From
US$2,811
Per Person
View Trip
19 Day Caribbean Holiday Cruise: San Juan, St. Barts & Curacao with Azamara Cruises
Cruise
 (3)

19 Days (18 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+8 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis
Azamara Always Included
Inside
-
Oceanview
$6,249
Balcony
$7,749
Suite
$12,299
From
US$6,249
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departure: 15 April 2028
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,041
Oceanview
$1,141
Balcony
$1,266
Suite
$3,216
From
US$1,233
Save 433
Per Person
View Trip
8 Day Southern Caribbean with Puerto Rico with Princess
Cruise
 (9)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Ship: Crown Princess
Departure: 05 February 2027
Visit: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Princess Standard
Inside
$1,049
Oceanview
$1,226
Balcony
$1,624
Suite
$1,849
From
US$1,049
Per Person
View Trip
11 Day Southern Caribbean with St. Lucia with Princess
Cruise
 (1)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Enchanted Princess
Departure: 14 December 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Saint Martin
Princess Standard
Inside
$1,179
Oceanview
$1,549
Balcony
$1,339
Suite
$2,000
From
US$1,179
Per Person
View Trip
15 Day Eastern/Western Caribbean with Celebration Key Holiday with Princess
Cruise
 (7)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 20 December 2026
Visit: USA, Puerto Rico, Turks and Caicos Islands, Bahamas, Mexico, Belize, Honduras
Princess Standard
Inside
$2,088
Oceanview
$2,618
Balcony
$3,128
Suite
$4,728
From
US$2,088
Per Person
View Trip
9 Day Southern Caribbean Islander Holiday with Princess
Cruise
 (9)

9 Days (8 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 19 December 2026
Visit: USA, Aruba, Curacao, Antigua and Barbuda, Virgin Islands, Puerto Rico
Princess Standard
Inside
$749
Oceanview
$1,089
Balcony
$1,324
Suite
$1,949
From
US$749
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Sep 2026 to Sep 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin
Princess Standard
Inside
$544
Oceanview
-
Balcony
$624
Suite
$849
From
US$544
Per Person
View Trip
8 Day Western Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 15 April 2027
Visit: USA, Cayman Islands, Jamaica, Bahamas
Inside
$1,043
Oceanview
$1,323
Balcony
$1,393
Suite
$3,633
From
US$1,043
Per Person
View Trip
10 Day Eastern Caribbean: U.S. And British Virgin Islands with Holland America
Cruise
 (3)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departures: Jan 2027 to Mar 2027
Visit: USA, Antigua and Barbuda, Virgin Islands, Puerto Rico, Bahamas
Fare Saver
Inside
$999
Oceanview
$1,199
Balcony
$1,499
Suite
$2,999
From
US$999
Per Person
View Trip
8 Day A Journey Into Timeless Marvels & Historical Tales of the West Indies with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 December 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Saint Martin, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise
 (3)

8 Days (7 Nights) Pointe-A-Pitre to Pointe-A-Pitre
Cruise Line: MSC Cruises
Ship: MSC World Europa
Departure: 20 December 2026
Visit: Guadeloupe, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, Dominica, Martinique
Inside
$1,553
Oceanview
$1,903
Balcony
$1,923
Suite
$4,863
From
US$1,553
Per Person
View Trip
10 Day Southern Caribbean: ABC Islands with Holland America
Cruise
 (3)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departure: 02 April 2027
Visit: USA, Bonaire, Curacao, Dominican Republic, Bahamas
Fare Saver
Inside
$1,099
Oceanview
$1,299
Balcony
$1,599
Suite
$3,199
From
US$1,099
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ships: MSC Meraviglia, MSC World Europa
Departures: Jan 2027 to Apr 2028
Visit: Martinique, Guadeloupe, Sint Maarten, Antigua and Barbuda, Saint Kitts and Nevis, Dominica
Inside
$886
Oceanview
$1,129
Balcony
$1,196
Suite
$1,596
From
US$886
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC World Europa
Departure: 23 March 2027
Visit: Barbados, Grenada, Saint Vincent, Martinique (+6 more), Guadeloupe, Sint Maarten, Antigua and Barbuda, Saint Kitts and Nevis, Dominica, Saint Lucia
Inside
$2,330
Oceanview
$2,910
Balcony
$2,950
Suite
$6,370
From
US$2,330
Per Person
View Trip
7 Day Eastern Caribbean with Celebration Key Holiday with Princess
Cruise
 (2)

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 21 December 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$909
Oceanview
-
Balcony
$1,029
Suite
$1,404
From
US$909
Per Person
View Trip
8 Day Grand Turk & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departure: 11 December 2027
Visit: USA, Turks and Caicos Islands, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$889
Oceanview
$989
Balcony
$1,194
Suite
$3,541
From
US$1,051
Save 374
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 26 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,265
Oceanview
$1,449
Balcony
$2,359
Suite
$2,842
From
US$1,898
Save 50
Per Person
View Trip
8 Day Southern Caribbean From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Dec 2026 to Feb 2027
Visit: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Inside
$1,569
Oceanview
$1,689
Balcony
$2,139
Suite
$2,819
From
US$1,569
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departure: 27 February 2028
Visit: USA, Bahamas, Virgin Islands, Saint Martin, Jamaica, Cayman Islands, Mexico
Princess Standard
Inside
$1,728
Oceanview
-
Balcony
$2,108
Suite
$3,448
From
US$1,728
Per Person
View Trip
8 Day Southern Caribbean with St. Lucia with Princess
Cruise
 (9)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Ship: Crown Princess
Departure: 15 January 2027
Visit: Barbados, Puerto Rico, Saint Martin, Martinique, Grenada, Saint Lucia
Princess Standard
Inside
$1,099
Oceanview
$1,252
Balcony
$1,674
Suite
$2,068
From
US$1,099
Per Person
View Trip
13 Day Miami to Bridgetown with Silversea
Cruise
 (1)

13 Days (12 Nights) Miami to Bridgetown
Cruise Line: Silversea
Ship: Silver Nova
Departure: 06 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy (+5 more), Saint Kitts and Nevis, Aruba, Curacao, Bonaire, Barbados
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,900
Suite
$12,300
From
US$7,900
Save 2,500
Per Person
View Trip
22 Day Transatlantic Crossing And Caribbean Celebration with Cunard
Cruise
 (6)

22 Days (21 Nights) New York to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 21 December 2027
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin, England
Bonus Onboard Credit
Value Fare
Inside
$3,086
Oceanview
$4,284
Balcony
$4,446
Suite
$11,689
From
US$3,086
Per Person
View Trip
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Caribbean & Bahamas Cruises

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Routes

Cruises from Baltimore to Baltimore Cruises from Barcelona to Fort Lauderdale Cruises from Barcelona to Lisbon Cruises from Barcelona to Rome Cruises from Barcelona to Barcelona Cruises from Barcelona to Miami Cruises from Boston to Boston Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Buenos Aires to Rio de Janeiro Cruises from Buenos Aires to Buenos Aires Cruises from Buenos Aires to Santiago Cruises from Cartagena to Cartagena Cruises from Colon to Colon Cruises from Fort Lauderdale to London Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort-de-France to Fort-de-France Cruises from Galveston to Galveston Cruises from Genoa to Genoa Cruises from Hamburg to London Cruises from Hamburg to Hamburg Cruises from Jacksonville to Jacksonville Cruises from La Romana to La Romana Cruises from Lisbon to Lisbon Cruises from Lisbon to London Cruises from Lisbon to Barcelona Cruises from Lisbon to Rome Cruises from London to Hamburg Cruises from London to Fort Lauderdale Cruises from London to Reykjavik Cruises from London to London Cruises from London to Lisbon Cruises from London to New York Cruises from Los Angeles to Miami Cruises from Los Angeles to Los Angeles Cruises from Marseille to Marseille Cruises from Miami to San Juan Cruises from Miami to Lisbon Cruises from Miami to Los Angeles Cruises from Miami to Rome Cruises from Miami to Bridgetown Cruises from Miami to Panama City Cruises from Miami to Barcelona Cruises from Miami to Miami Cruises from Miami to London Cruises from Montreal to Boston Cruises from Montreal to Miami Cruises from Montreal to New York Cruises from New Orleans to New Orleans Cruises from New York to New York Cruises from New York to London Cruises from Orlando to Orlando Cruises from Paris to Paris Cruises from Philadelphia to Philadelphia Cruises from Philipsburg to Bridgetown Cruises from Pointe-A-Pitre to Pointe-A-Pitre Cruises from Quebec City to Boston Cruises from Reykjavik to London Cruises from Reykjavik to Reykjavik Cruises from Rio de Janeiro to Buenos Aires Cruises from Rio de Janeiro to Rio de Janeiro Cruises from Rio de Janeiro to Barcelona Cruises from Rome to Lisbon Cruises from Rome to Miami Cruises from Rome to Barcelona Cruises from Rome to Fort Lauderdale Cruises from Rome to Rome Cruises from San Francisco to San Francisco Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Santiago to Buenos Aires Cruises from Santiago to Santiago Cruises from Seattle to Seattle Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa Cruises from Vancouver to Los Angeles Cruises from Vancouver to Seattle Cruises from Venice to Barcelona Cruises from Venice to Rome

Country Routes

Cruises from Peru to Argentina Cruises from USA to Portugal Cruises from USA to Germany Cruises from Germany to England Cruises from France to Spain Cruises from Portugal to England Cruises from Iceland to USA Cruises from Puerto Rico to USA Cruises from Portugal to France Cruises from Chile to USA Cruises from USA to Iceland Cruises from France to Brazil Cruises from Brazil to France Cruises from France to USA Cruises from Iceland to Canada Cruises from England to Canada Cruises from England to Germany Cruises from Singapore to China Cruises from Brazil to Portugal Cruises from Dominican Republic to USA Cruises from Brazil to Spain Cruises from USA to Puerto Rico Cruises from Argentina to Brazil Cruises from USA to Brazil Cruises from Argentina to Chile Cruises from Brazil to Italy Cruises from Argentina to USA Cruises from Peru to USA Cruises from Barbados to USA Cruises from Brazil to Argentina Cruises from Canada to USA Cruises from Chile to Argentina Cruises from England to Iceland Cruises from England to Spain Cruises from England to USA Cruises from France to Italy Cruises from Saint Martin to Barbados Cruises from USA to Dominican Republic Cruises from Iceland to England Cruises from Italy to Brazil Cruises from Italy to France Cruises from Italy to Portugal Cruises from Italy to Spain Cruises from Italy to USA Cruises from Panama to USA Cruises from Spain to Brazil Cruises from Portugal to Italy Cruises from Portugal to Spain Cruises from Portugal to USA Cruises from Barbados to Saint Martin Cruises from Spain to France Cruises from Spain to Italy Cruises from Spain to Portugal Cruises from Spain to USA Cruises from USA to Argentina Cruises from USA to Barbados Cruises from USA to Canada Cruises from England to Portugal Cruises from USA to Chile Cruises from USA to England Cruises from USA to Italy Cruises from Spain to England Cruises from USA to Panama Cruises from USA to Peru Cruises from USA to Spain

Cruise Lines Exploring The Caribbean & Bahamas

Azamara Caribbean Cruises Celebrity Caribbean Cruises Cunard Caribbean Cruises Emerald Caribbean Cruises Explora Journeys Caribbean Cruises Holland America Caribbean Cruises MSC Caribbean Cruises NCL Caribbean Cruises Oceania Caribbean Cruises Ponant Caribbean Cruises Princess Caribbean Cruises Regent Seven Seas Caribbean Cruises Royal Caribbean Caribbean Cruises Scenic Caribbean Cruises Seabourn Caribbean Cruises Silversea Caribbean Cruises Viking Caribbean Cruises Virgin Voyages Caribbean Cruises

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