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Caribbean Cruises Starting In January 2027 and 2028

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486 Cruises (2,596 Cruise Departures)
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico
Inside
$389
Oceanview
$509
Balcony
$679
Suite
$1,511
From
US$389
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,448
From
US$674
Save 571
Per Person
View Trip
11 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Brilliant Lady
Departures: Nov 2026 to Mar 2027
Visit: USA, Saint Martin, Virgin Islands, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,090
Oceanview
$1,390
Balcony
$1,690
Suite
$4,990
From
US$1,090
Per Person
View Trip
9 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Nov 2027 to Mar 2028
Visit: USA, Cayman Islands, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$909
Balcony
$1,175
Suite
$1,883
From
US$840
Save 477
Per Person
View Trip
13 Day Panama Canal From Miami To Miami with Norwegian Cruise Line
Cruise
 (1)

13 Days (12 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Sun
Departures: Dec 2026 to Mar 2027
Visit: USA, Bahamas, Dominican Republic, Aruba (+4 more), Curacao, Colombia, Panama, Costa Rica
Inside
$1,989
Oceanview
$2,169
Balcony
$3,449
Suite
$5,149
From
US$1,989
Per Person
View Trip
8 Day Western Caribbean 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
Departures: Dec 2026 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$829
Oceanview
$1,209
Balcony
$1,109
Suite
$1,209
From
US$829
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: 23 January 2028
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Bonaire, Curacao
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
Per Person
View Trip
11 Day Eastern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Brilliant Lady
Departure: 24 January 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin
Inside
$1,290
Oceanview
$1,491
Balcony
$1,790
Suite
$4,950
From
US$1,290
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
$1,288
Oceanview
$1,864
Balcony
$1,782
Suite
$2,768
From
US$1,288
Per Person
View Trip
6 Day Grand Cayman & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2026 to Apr 2028
Visit: USA, Cayman Islands, Bahamas
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,645
From
US$595
Per Person
View Trip
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise
 (3)

15 Days (14 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra
Departures: Jan 2027 to Mar 2027
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$12,690
Balcony
-
Suite
$12,950
From
US$12,950
Save 2,820
Per Person
View Trip
6 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visit: USA, Mexico, Bahamas
Inside
$439
Oceanview
$599
Balcony
$799
Suite
$869
From
US$439
Per Person
View Trip
8 Day A Journey into Dominican Charm & Caribbean Splendour with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 30 January 2028
Visit: USA, Dominican Republic, Virgin Islands, Anguilla, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$3,755
From
US$3,755
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departures: Dec 2026 to Mar 2027
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$4,288
Balcony
-
Suite
$5,687
From
US$4,288
Save 1,857
Per Person
View Trip
8 Day Key West, Cayman & Jamaica with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departure: 29 January 2028
Visit: USA, Jamaica, Cayman Islands
Exclusive Savings
Inside
$854
Oceanview
$954
Balcony
$1,079
Suite
$2,984
From
US$854
Save 542
Per Person
View Trip
71 Day Grand South America & Antarctica Voyage with Holland America
Cruise
 (3)

71 Days (70 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Zaandam
Departure: 03 January 2027
Visit: 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
Advantage Fare
Inside
$15,614
Oceanview
$17,414
Balcony
$31,014
Suite
$62,014
From
US$15,614
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
8 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 03 January 2027
Visit: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Princess Standard
Sanctuary Collection
Inside
$679
Oceanview
$759
Balcony
$934
Suite
$1,199
From
US$679
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 (+3 more), Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$729
Oceanview
$789
Balcony
$889
Suite
$1,049
From
US$729
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (2)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Dec 2027 to Jan 2028
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Inside
$554
Oceanview
$729
Balcony
$741
Suite
$1,119
From
US$554
Per Person
View Trip
13 Day Panama Canal Discovery: Costa Rica & Greater Antilles with Holland America
Cruise
 (3)

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Nieuw Amsterdam, Oosterdam
Departures: Oct 2026 to Mar 2028
Visit: USA, Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Book Early & Have It All Fare Option
Inside
$1,249
Oceanview
$1,299
Balcony
$1,899
Suite
$3,799
From
US$1,249
Per Person
View Trip
35 Day South America Cruise: Miami, Rio De Janeiro & Buenos Aires with Azamara Cruises
Cruise
 (3)

35 Days (34 Nights) Miami to Buenos Aires
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 14 January 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Kitts and Nevis (+10 more), Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Barbados, Trinidad and Tobago, French Guiana, Brazil, Uruguay, Argentina
Azamara Always Included
Inside
$12,329
Oceanview
$12,429
Balcony
$14,739
Suite
$23,149
From
US$12,329
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departures: Jan 2027 to Jan 2027
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$634
Oceanview
$1,039
Balcony
$824
Suite
$1,199
From
US$634
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Jan 2027 to Apr 2028
Visit: Panama, Colombia, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$888
Oceanview
$997
Balcony
$1,400
Suite
$1,400
From
US$888
Save 828
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (7)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departures: Nov 2027 to Jan 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico (+4 more), Turks and Caicos Islands, Belize, Honduras, Mexico
Princess Standard
Sanctuary Collection
Inside
$1,528
Oceanview
$1,828
Balcony
$2,128
Suite
$3,068
From
US$1,528
Per Person
View Trip
8 Day Eastern Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Luna
Departures: Dec 2027 to Jan 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$1,209
Oceanview
$1,329
Balcony
$1,499
Suite
$2,119
From
US$1,209
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: Nov 2026 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Inside
$1,259
Oceanview
$1,459
Balcony
$1,699
Suite
$1,949
From
US$1,259
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,414
From
US$834
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
$1,169
Oceanview
$1,328
Balcony
$1,774
Suite
$2,195
From
US$1,169
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
$1,698
Oceanview
$1,838
Balcony
$2,268
Suite
$3,058
From
US$1,698
Per Person
View Trip
Results: 91-120 of 486

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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 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 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 Seattle Cruises from Singapore Cruises from Tampa Cruises from Valparaiso Cruises from Vancouver Cruises from Vancouver

Routes

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 Barcelona Cruises from London to Fort Lauderdale Cruises from London to Reykjavik 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 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 France to Iceland Cruises from Brazil to Spain Cruises from USA to Puerto Rico Cruises from Canada to England 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 Italy 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 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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