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Caribbean Cruises Starting In January 2027, 2028 and 2029

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559 Cruises (2,846 Departures)
559 Cruises (2,846 Departures)
Departures
Duration
5 Days
141 Days
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$400pp
$209,450pp
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8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departures: Dec 2026 to Apr 2027
Visits: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$1,287
Oceanview
$1,387
Balcony
$1,487
Suite
$4,977
From (Per Person)
A$1,287
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Thomas with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 31 January 2027
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$892
Oceanview
$1,027
Balcony
$1,902
Suite
$2,337
From (Per Person)
A$892
Per Person
View Trip
13 Day Caribbean Cruise From Philadelphia To Philadelphia with Norwegian Cruise Line
Cruise
 (1)

13 Days (12 Nights) Philadelphia to Philadelphia
Operator: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 03 January 2028
Visits: USA, Saint Martin, Barbados, Saint Lucia, Antigua and Barbuda, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$1,893
Oceanview
$2,265
Balcony
$3,009
Suite
$3,650
From (Per Person)
A$1,893
Per Person
View Trip
8 Day A Journey Across Caribbean Culture & Volcanic Landscapes with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Explora Journeys
Ship: Explora II
Departure: 16 January 2028
Visits: Puerto Rico, Saint Vincent, Saint Lucia, Barbados, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sun Princess
Departures: Jan 2027 to Mar 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$972
Oceanview
$1,289
Balcony
$1,982
Suite
$2,378
From (Per Person)
A$972
Per Person
View Trip
12 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

12 Days (11 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departures: Jan 2027 to Jan 2028
Visits: USA, Jamaica, Colombia, Panama, Costa Rica, Honduras, Belize
Exclusive Savings
Inside
$1,950
Oceanview
$2,118
Balcony
$2,574
Suite
$7,385
From (Per Person)
A$1,950
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 17 January 2027
Visits: Puerto Rico, Bonaire, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,003
Oceanview
$2,107
Balcony
$2,405
Suite
$2,703
From (Per Person)
A$2,003
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visits: Puerto Rico, Saint Martin, Barbados, Martinique, Saint Kitts and Nevis, Virgin Islands
Inside
$1,087
Oceanview
$1,685
Balcony
$1,885
Suite
$5,279
From (Per Person)
A$1,087
Per Person
View Trip
9 Day Western Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departures: Jan 2027 to Mar 2027
Visits: USA, Mexico, Honduras, Belize, Bahamas
Inside
$1,585
Oceanview
$1,699
Balcony
$1,812
Suite
$4,663
From (Per Person)
A$1,585
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Operator: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Jan 2028 to Mar 2028
Visits: Panama, Colombia, Curacao, Aruba
Exclusive Savings
Inside
$1,544
Oceanview
$1,746
Balcony
$2,363
Suite
$2,700
From (Per Person)
A$1,544
Save 892
Per Person
View Trip
6 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

6 Days (5 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 03 January 2028
Visits: USA, Honduras, Mexico
Exclusive Savings
Inside
$1,012
Oceanview
$1,080
Balcony
$1,355
Suite
$2,243
From (Per Person)
A$1,012
Save 505
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ships: MSC Grandiosa, MSC World Atlantic
Departures: Nov 2026 to Nov 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$744
Oceanview
$923
Balcony
$1,190
Suite
$2,507
From (Per Person)
A$744
Save 15
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 02 January 2028
Visits: Puerto Rico, Saint Vincent, Barbados, Dominica, Saint Martin
Inside
$931
Oceanview
$1,445
Balcony
$1,616
Suite
$4,524
From (Per Person)
A$931
Per Person
View Trip
7 Day Caribbean Sojourn with Emerald Cruises
New ReleaseCruise
 (3)

7 Days (6 Nights) Bridgetown to Marigot
Operator: Emerald Cruises
Ship: Emerald Azzurra
Departure: 03 January 2027
Visits: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Exclusive Savings
Oceanview
-
Balcony
-
Suite
$19,922
From (Per Person)
A$19,922
Save 3,393
Per Person
View Trip
11 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departure: 14 January 2027
Visits: USA, Curacao, Aruba, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$2,312
Oceanview
$2,312
Balcony
$2,649
Suite
$7,085
From (Per Person)
A$2,312
Per Person
View Trip
7 Day Eastern Caribbean with Turks & Caicos & Celebration Key with Princess
Cruise
 (1)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departure: 17 January 2027
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$917
Oceanview
-
Balcony
$1,222
Suite
$1,923
From (Per Person)
A$917
Per Person
View Trip
11 Day Southern Caribbean with St. Lucia with Princess
Cruise
 (2)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Enchanted Princess
Departures: Jan 2028 to Feb 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Saint Martin
Exclusive Savings
Inside
$1,586
Oceanview
$2,289
Balcony
$2,428
Suite
$3,051
From (Per Person)
A$1,586
Per Person
View Trip
8 Day Pearls of the Caribbean with Ponant
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Operator: Ponant
Ship: Le Bougainville
Departures: Dec 2026 to Feb 2027
Visits: Martinique, Saint Vincent, Saint Lucia, Guadeloupe
Exclusive Savings
Balcony
$7,585
Suite
$11,242
From (Per Person)
A$7,585
Save 467
Per Person
View Trip
13 Day Caribbean Cruise From Philadelphia To Philadelphia with Norwegian Cruise Line
Cruise
 (1)

13 Days (12 Nights) Philadelphia to Philadelphia
Operator: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 15 January 2028
Visits: USA, Saint Martin, Saint Lucia, Barbados, Antigua and Barbuda, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$2,101
Oceanview
$2,459
Balcony
$3,158
Suite
$3,650
From (Per Person)
A$2,101
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

8 Days (7 Nights) Pointe-A-Pitre to Pointe-A-Pitre
Operator: MSC Cruises
Ship: MSC World Europa
Departures: Dec 2026 to Mar 2027
Visits: Guadeloupe, Saint Lucia, Barbados, Saint Vincent, Grenada, Martinique
Exclusive Savings
Inside
$1,895
Oceanview
$1,964
Balcony
$2,102
Suite
$3,845
From (Per Person)
A$1,895
Per Person
View Trip
9 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

9 Days (8 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Nov 2027 to Mar 2028
Visits: USA, Cayman Islands, Mexico, Honduras
Exclusive Savings
Inside
$1,329
Oceanview
$1,423
Balcony
$1,712
Suite
$2,898
From (Per Person)
A$1,329
Save 786
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Operator: Princess
Ship: Regal Princess
Departures: Dec 2027 to Feb 2028
Visits: USA, Bahamas, Virgin Islands, Saint Martin, Belize, Honduras, Mexico
Exclusive Savings
Inside
$1,846
Oceanview
-
Balcony
$2,276
Suite
$3,024
From (Per Person)
A$1,846
Per Person
View Trip
12 Day Best Of Southern Caribbean with Celebrity Cruises
Cruise
 (1)

12 Days (11 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Ship: Celebrity Ascent
Departures: Dec 2026 to Mar 2027
Visits: USA, Sint Maarten, Antigua and Barbuda, Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis
Exclusive Savings
Inside
$2,117
Oceanview
$2,551
Balcony
$3,576
Suite
$10,833
From (Per Person)
A$2,117
Save 2,228
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (7)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sun Princess
Departures: Dec 2026 to Jan 2027
Visits: USA, Mexico, Belize, Honduras, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$2,053
Oceanview
$4,271
Balcony
$3,869
Suite
$5,837
From (Per Person)
A$2,053
Save 31
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
Operator: MSC Cruises
Ship: MSC World Europa
Departures: Dec 2026 to Mar 2027
Visits: Martinique, Guadeloupe, Saint Lucia, Barbados, Saint Vincent, Grenada
Exclusive Savings
Inside
$1,499
Oceanview
$1,756
Balcony
$2,053
Suite
$3,944
From (Per Person)
A$1,499
Per Person
View Trip
8 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departure: 02 January 2028
Visits: USA, Bahamas, Dominican Republic
Inside
$1,188
Oceanview
$1,587
Balcony
$1,886
Suite
$4,782
From (Per Person)
A$1,188
Per Person
View Trip
11 Day Classic Canal & Tropics with Oceania Cruises
Cruise
 (4)

11 Days (10 Nights) Panama City to Miami
Operator: Oceania
Ship: Oceania Marina
Departure: 16 January 2028
Visits: Panama, Colombia, Curacao, Aruba, Jamaica, Cayman Islands, USA
Your World Inclusions
Exclusive Savings
Inside
$4,721
Oceanview
$6,225
Balcony
$7,428
Suite
$10,435
From (Per Person)
A$4,721
Save 2,089
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departures: Dec 2027 to Mar 2028
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,355
Oceanview
$1,926
Balcony
$2,154
Suite
$5,407
From (Per Person)
A$1,355
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Operator: Princess
Ship: Regal Princess
Departures: Jan 2028
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic, Bahamas, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,686
Oceanview
-
Balcony
$2,330
Suite
$3,736
From (Per Person)
A$1,686
Per Person
View Trip
71 Day Grand South America & Antarctica Voyage with Holland America
Cruise
 (5)

71 Days (70 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Holland America
Ship: Zaandam
Departure: 03 January 2027
Visits: USA, Cayman Islands, Panama, Ecuador +12 more, Peru, Chile, Argentina, Antarctica, Falkland Islands, Uruguay, Brazil, French Guiana, Barbados, Saint Lucia, Saint Kitts and Nevis, Puerto Rico
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$21,406
Oceanview
$24,376
Balcony
$44,176
Suite
$87,043
From (Per Person)
A$21,406
Per Person
View Trip
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Caribbean & Bahamas Cruises

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Travel Styles

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Countries

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Cities

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Routes

Cruises from Athens to Lisbon Cruises from Athens to Barcelona Cruises from Athens to Rome Cruises from Athens to Venice Cruises from Barcelona to Fort Lauderdale Cruises from Barcelona to Lisbon Cruises from Barcelona to London Cruises from Barcelona to Rome Cruises from Barcelona to Venice 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 Los Angeles Cruises from Fort Lauderdale to London Cruises from Fort Lauderdale to Barcelona Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort Lauderdale to San Diego 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 Miami Cruises from Lisbon to Barcelona Cruises from Lisbon to Rome Cruises from London to Hamburg Cruises from London to Barcelona Cruises from London to Fort Lauderdale Cruises from London to Rome 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 Panama City to Miami Cruises from Philadelphia to Philadelphia Cruises from Philipsburg to Bridgetown Cruises from Pointe-A-Pitre to Pointe-A-Pitre Cruises from Reykjavik to London Cruises from Rio de Janeiro to Buenos Aires Cruises from Rio de Janeiro to Lisbon Cruises from Rio de Janeiro to Rio de Janeiro Cruises from Rio de Janeiro to Barcelona Cruises from Rome to London Cruises from Rome to Lisbon Cruises from Rome to Miami Cruises from Rome to Barcelona Cruises from Rome to Venice 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 Vancouver to San Diego

Country Routes

Cruises from Peru to Argentina Cruises from Australia to England Cruises from USA to Portugal Cruises from Italy to England Cruises from Greece to Portugal 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 France to Brazil Cruises from Brazil to France Cruises from Iceland 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 Australia 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 Italy Cruises from England to Spain Cruises from England to USA Cruises from France to Italy Cruises from Saint Martin to Barbados Cruises from Greece to Italy Cruises from Greece to Spain 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 Greece to USA 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 Crystal 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 P&O (UK) 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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