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Caribbean Cruises Starting In January 2027 and 2028

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482 Cruises (2,750 Cruise Departures)
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
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$5,658
Balcony
-
Suite
$7,186
From
US$5,658
Save 788
Per Person
View Trip
8 Day Eastern Caribbean with St. Thomas with Princess
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departures: Dec 2027 to Apr 2028
Visit: USA, Bahamas, Virgin Islands, Saint Martin
Princess Standard
Inside
$799
Oceanview
-
Balcony
$974
Suite
$1,349
From
US$799
Per Person
View Trip
8 Day Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic, Norwegian Prima
Departures: Mar 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$759
Oceanview
$929
Balcony
$1,049
Suite
$1,319
From
US$759
Per Person
View Trip
9 Day Western Caribbean Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Radiance of the Seas
Departures: Jan 2027 to Mar 2027
Visit: USA, Mexico, Honduras, Belize, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$793
Oceanview
$923
Balcony
$1,116
Suite
$1,811
From
US$793
Save 502
Per Person
View Trip
8 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departures: Jan 2027 to Mar 2027
Visit: USA, Bahamas, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$812
Oceanview
$903
Balcony
$1,215
Suite
$1,850
From
US$812
Save 451
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Apr 2028
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+4 more), Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Saint Martin
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$5,561
Balcony
-
Suite
$7,089
From
US$5,561
Save 785
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Apr 2027 to Apr 2028
Visit: USA, Dominican Republic, Bahamas
Limited Time Offer
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,875
From
US$595
Per Person
View Trip
10 Day Belize, Costa Rica & Panama Cruise: Belize City, Puerto Limon & Panama City with Azamara Cruises
Cruise
 (5)

10 Days (9 Nights) Miami to Panama City
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 05 January 2028
Visit: USA, Mexico, Belize, Honduras, Costa Rica, Panama
Azamara Always Included
Exclusive Savings
Inside
$2,944
Oceanview
$3,410
Balcony
$4,070
Suite
$5,680
From
US$2,944
Save 55
Per Person
View Trip
8 Day Caribbean Yachting Hideaways with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Montserrat, Antigua and Barbuda
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,071
Balcony
-
Suite
$7,660
From
US$6,071
Save 818
Per Person
View Trip
7 Day Western Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Jan 2027 to Mar 2027
Visit: USA, Jamaica, Haiti, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$541
Oceanview
$651
Balcony
$853
Suite
$1,419
From
US$541
Save 370
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Pointe-A-Pitre to Pointe-A-Pitre
Cruise Line: MSC Cruises
Ships: MSC Meraviglia, MSC Seaview
Departures: Jan 2027 to Apr 2028
Visit: Guadeloupe, Sint Maarten, Antigua and Barbuda, Saint Kitts and Nevis, Dominica, Martinique
Inside
$862
Oceanview
$1,061
Balcony
$1,229
Suite
$1,642
From
US$862
Per Person
View Trip
8 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Nov 2027 to Jan 2028
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Limited Time Offer
Inside
$833
Oceanview
$1,043
Balcony
$1,253
Suite
$3,500
From
US$833
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 Prima
Departures: Feb 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,259
Oceanview
$1,429
Balcony
$1,579
Suite
$2,041
From
US$1,259
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
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 16 January 2028
Visit: Puerto Rico, Saint Vincent, Saint Lucia, Barbados, Antigua and Barbuda, Saint Kitts and Nevis
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
8 Day A Journey to Island Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Jan 2028 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$3,655
From
US$3,655
Per Person
View Trip
11 Day Caribbean Island Hopping: Sint Maarten to Barbados with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 12 January 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Select Fare
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$8,773
Balcony
-
Suite
$10,956
From
US$8,773
Save 1,122
Per Person
View Trip
22 Day Eastern Caribbean & Panama Canal: U.S. Virgin Islands with Holland America
Cruise
 (3)

22 Days (21 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 (+6 more), Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Inside
$2,539
Oceanview
$2,819
Balcony
$3,819
Suite
$7,407
From
US$2,539
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
Departures: Dec 2026 to Mar 2027
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,238
Suite
$22,370
From
US$9,238
Save 201
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 09 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,708
Oceanview
$1,942
Balcony
$2,708
Suite
$3,245
From
US$1,708
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (6)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departures: Nov 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico (+4 more), Turks and Caicos Islands, Belize, Honduras, Mexico
Princess Standard
Inside
$1,448
Oceanview
$1,828
Balcony
$2,148
Suite
$2,898
From
US$1,448
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
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic (+4 more), Norwegian Escape, Norwegian Getaway, Norwegian Joy, Norwegian Prima
Departures: Apr 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$719
Oceanview
$859
Balcony
$989
Suite
$1,179
From
US$719
Per Person
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,558
Oceanview
$1,795
Balcony
$2,478
Suite
$3,137
From
US$1,558
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
Cruise Line: Princess
Ship: Regal Princess
Departures: Nov 2026 to Feb 2027
Visit: USA, Bahamas, Turks and Caicos Islands
Princess Standard
Inside
$489
Oceanview
-
Balcony
$654
Suite
$889
From
US$489
Per Person
View Trip
8 Day Southern Caribbean with St. Lucia with Princess
Cruise
 (7)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Mar 2028
Visit: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$990
Oceanview
$1,139
Balcony
$1,485
Suite
$1,650
From
US$990
Per Person
View Trip
5 Day San Juan To Ft. Lauderdale with Celebrity Cruises
Cruise

5 Days (4 Nights) San Juan to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 02 January 2028
Visit: Puerto Rico, Saint Martin, USA
Exclusive Savings
Inside
$506
Oceanview
$526
Balcony
$552
Suite
$1,963
From
US$506
Save 296
Per Person
View Trip
11 Day Southern Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Jewel
Departures: Nov 2026 to Jan 2028
Visit: USA, Bahamas, Dominican Republic, Aruba, Curacao, Jamaica, Cayman Islands
Inside
$1,059
Oceanview
$1,109
Balcony
$1,948
Suite
$2,152
From
US$1,059
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (2)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Jan 2028 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands (+4 more), Mexico, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$1,253
Oceanview
$1,912
Balcony
$1,884
Suite
$2,908
From
US$1,253
Per Person
View Trip
11 Day Southern Caribbean Cruise From Tampa To Tampa with Norwegian Cruise Line
Cruise
 (1)

11 Days (10 Nights) Tampa to Tampa
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Gem
Departure: 18 January 2027
Visit: USA, Dominican Republic, Curacao, Aruba, Jamaica, Cayman Islands
Inside
$1,249
Oceanview
$1,369
Balcony
$2,255
Suite
$2,400
From
US$1,249
Per Person
View Trip
Results: 91-120 of 482

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Travel Styles

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Countries

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Cities

Cruises from Baltimore Cruises from Boston Cruises from Bridgetown Cruises from Cartagena Cruises from Colon Cruises from Fort Lauderdale Cruises from Fort-de-France Cruises from Galveston Cruises from Jacksonville Cruises from La Romana Cruises from Los Angeles Cruises from Marigot Cruises from Miami Cruises from Montreal Cruises from New Orleans Cruises from New York Cruises from Orlando Cruises from Panama City Cruises from Philadelphia Cruises from Philipsburg Cruises from Quebec City Cruises from Reykjavik Cruises from San Francisco Cruises from San Juan Cruises from San Juan Cruises from San Juan Cruises from Santiago Cruises from Seattle Cruises from Singapore Cruises from Tampa Cruises from Valparaiso Cruises from Vancouver Cruises from Vancouver

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 Los Angeles Cruises from Fort Lauderdale to London Cruises from Fort Lauderdale to Barcelona 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 Panama City to Miami 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 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 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 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 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 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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