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Puerto Rico Cruises Starting In January 2027, 2028 and 2029

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60 Cruises (248 Departures)
60 Cruises (248 Departures)
Departures
Duration
5 Days
15 Days
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$500pp
$28,620pp
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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: 03 January 2027
Visits: USA, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,108
Oceanview
$1,209
Balcony
$1,311
Suite
$3,647
From (Per Person)
A$1,108
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: 31 January 2027
Visits: Puerto Rico, Curacao, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$1,472
Oceanview
$1,496
Balcony
$1,734
Suite
$2,416
From (Per Person)
A$1,472
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
$1,266
Oceanview
$1,287
Balcony
$1,548
Suite
$2,120
From (Per Person)
A$1,266
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
$950
Oceanview
$1,472
Balcony
$1,646
Suite
$4,615
From (Per Person)
A$950
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Dec 2027 to Feb 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,135
Oceanview
$1,263
Balcony
$1,994
Suite
$2,459
From (Per Person)
A$1,135
Save 727
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Celebrity Cruises
Ship: Celebrity Apex
Departure: 22 January 2028
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,678
Oceanview
$1,818
Balcony
$1,955
Suite
$4,414
From (Per Person)
A$2,828
Save 45
Per Person
View Trip
11 Day Caribbean Cruise From Philadelphia To Philadelphia with Norwegian Cruise Line
Cruise
 (1)

11 Days (10 Nights) Philadelphia to Philadelphia
Operator: Norwegian Cruise Line
Ship: Norwegian Pearl
Departures: Nov 2026 to Feb 2028
Visits: USA, Virgin Islands, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$1,377
Oceanview
$1,496
Balcony
$2,627
Suite
$2,583
From (Per Person)
A$1,377
Per Person
View Trip
10 Day A Journey from From Hidden Shores to Timeless Elegance with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Operator: Explora Journeys
Ship: Explora I
Departure: 11 January 2027
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Suite
$8,472
From (Per Person)
A$8,472
Save 173
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Star Princess, Sun Princess
Departures: Nov 2027 to Mar 2029
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$896
Oceanview
$1,094
Balcony
$1,133
Suite
$1,787
From (Per Person)
A$896
Per Person
View Trip
11 Day Caribbean Cruise From Jacksonville to Jacksonville with Norwegian Cruise Line
Cruise

11 Days (10 Nights) Jacksonville to Jacksonville
Operator: Norwegian Cruise Line
Ship: Norwegian Dawn
Departure: 28 January 2028
Visits: USA, Bahamas, Dominican Republic, Virgin Islands, Puerto Rico
Just Cruise Fare
Exclusive Savings
Inside
$1,897
Oceanview
$2,150
Balcony
$2,850
Suite
$3,282
From (Per Person)
A$1,897
Per Person
View Trip
9 Day Caribbean And Antilles with MSC Cruises
Cruise

9 Days (8 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Meraviglia
Departure: 30 January 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin, Virgin Islands
Exclusive Savings
Inside
$700
Oceanview
$927
Balcony
$1,125
Suite
$3,897
From (Per Person)
A$700
Per Person
View Trip
10 Day Paradise Beaches from the U.S. Virgin Islands to the Bahamas with Emerald Cruises
New ReleaseCruise

10 Days (9 Nights) San Juan to Miami
Operator: Emerald Cruises
Ships: Emerald Kaia
Departures: Feb 2028 to Feb 2029
Visits: Puerto Rico, Virgin Islands, Turks and Caicos Islands, Bahamas, USA
Exclusive Savings
Oceanview
$9,733
Balcony
$12,031
Suite
$19,260
From (Per Person)
A$9,733
Save 4,173
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 15 January 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,821
Oceanview
$1,956
Balcony
$2,079
Suite
$4,155
From (Per Person)
A$1,821
Save 977
Per Person
View Trip
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Independence of the Seas
Departures: Nov 2027 to Jan 2028
Visits: USA, Dominican Republic, Puerto Rico, Aruba, Curacao
Exclusive Savings
Inside
$1,514
Oceanview
$1,681
Balcony
$2,036
Suite
$3,404
From (Per Person)
A$1,514
Save 852
Per Person
View Trip
8 Day A Journey Of Sun-hazed Island Enchantment & Caribbean Treasures with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Operator: Explora Journeys
Ship: Explora III
Departure: 29 January 2027
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Turks and Caicos Islands, USA
Exclusive Savings
Suite
$9,673
From (Per Person)
A$9,673
Save 197
Per Person
View Trip
15 Day Festive Crossing with Oceania Cruises
Cruise

15 Days (14 Nights) Lisbon to Miami
Operator: Oceania
Ship: Oceania Aurelia
Departure: 04 January 2028
Visits: Portugal, Spain, Puerto Rico, USA
Your World Inclusions
Exclusive Savings
Inside
$4,334
Oceanview
$4,887
Balcony
$6,973
Suite
$7,671
From (Per Person)
A$4,334
Save 2,116
Per Person
View Trip
10 Day Seagrass & Sky with Regent Seven Seas
Cruise

10 Days (9 Nights) Miami to Miami
Operator: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 29 January 2029
Visits: USA, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,271
Suite
$9,736
From (Per Person)
A$9,271
Save 6,189
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Nov 2026 to Apr 2028
Visits: USA, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,141
Oceanview
$1,235
Balcony
$961
Suite
$3,209
From (Per Person)
A$961
Save 1,534
Per Person
View Trip
8 Day Perfect Day Cococay & Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ships: Allure of the Seas, Independence of the Seas
Departures: Nov 2026 to Apr 2027
Visits: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$587
Oceanview
$1,249
Balcony
$1,272
Suite
$3,222
From (Per Person)
A$587
Save 1,187
Per Person
View Trip
11 Day Caribbean Cruise From Jacksonville To Jacksonville with Norwegian Cruise Line
Cruise

11 Days (10 Nights) Jacksonville to Jacksonville
Operator: Norwegian Cruise Line
Ship: Norwegian Dawn
Departure: 18 January 2028
Visits: USA, Bahamas, Dominican Republic, Virgin Islands, Puerto Rico
Just Cruise Fare
Exclusive Savings
Inside
$1,911
Oceanview
$2,105
Balcony
$2,909
Suite
$3,296
From (Per Person)
A$1,911
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 03 January 2028
Visits: Puerto Rico, Bonaire, Curacao, Aruba
Exclusive Savings
Inside
$1,116
Oceanview
$1,189
Balcony
$2,071
Suite
$2,270
From (Per Person)
A$1,116
Save 695
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) Saint Thomas to San Juan
Operator: Emerald Cruises
Ship: Emerald Sakara
Departure: 03 January 2027
Visits: Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
Exclusive Savings
Oceanview
-
Balcony
$6,055
Suite
$8,377
From (Per Person)
A$6,055
Save 4,610
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ships: Star Princess, Sun Princess
Departures: Oct 2027 to Jan 2029
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$816
Oceanview
$994
Balcony
$1,133
Suite
$1,509
From (Per Person)
A$816
Per Person
View Trip
12 Day Eastern Caribbean From New York To New York with Norwegian Cruise Line
Cruise

12 Days (11 Nights) New York to New York
Operator: Norwegian Cruise Line
Ship: Norwegian Bliss
Departure: 15 January 2028
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,238
Oceanview
$2,520
Balcony
$2,862
Suite
$3,220
From (Per Person)
A$2,238
Per Person
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Independence of the Seas
Departure: 24 January 2027
Visits: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,152
Oceanview
$1,661
Balcony
$2,524
Suite
$7,393
From (Per Person)
A$1,152
Save 632
Per Person
View Trip
8 Day Eastern Caribbean: San Juan & St. Thomas with Holland America
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Holland America
Ships: Eurodam, Nieuw Statendam, Rotterdam
Departures: Nov 2026 to Mar 2028
Visits: USA, Turks and Caicos Islands, Puerto Rico, Virgin Islands, Bahamas
Exclusive Savings
Inside
$923
Oceanview
$1,081
Balcony
$1,536
Suite
$2,536
From (Per Person)
A$923
Save 18
Per Person
View Trip
6 Day Beaches of the Virgin Islands with Emerald Cruises
New ReleaseCruise

6 Days (5 Nights) San Juan to San Juan
Operator: Emerald Cruises
Ship: Emerald Kaia
Departures: Jan 2028 to Feb 2028
Visits: Puerto Rico, Virgin Islands
Exclusive Savings
Oceanview
$5,744
Balcony
$7,214
Suite
$11,012
From (Per Person)
A$5,744
Save 2,101
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 29 January 2028
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,782
Oceanview
$1,876
Balcony
$1,867
Suite
$4,047
From (Per Person)
A$1,782
Save 958
Per Person
View Trip
5 Day San Juan To Ft. Lauderdale with Celebrity Cruises
Cruise

5 Days (4 Nights) San Juan to Fort Lauderdale
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 02 January 2028
Visits: Puerto Rico, Saint Martin, USA
Exclusive Savings
Inside
$734
Oceanview
$765
Balcony
$778
Suite
$2,652
From (Per Person)
A$1,244
Save 33
Per Person
View Trip
7 Day Caribbean & Perfect Day with Royal Caribbean
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Legend Of The Seas
Departure: 03 January 2027
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$2,094
Oceanview
$2,616
Balcony
$2,476
Suite
$3,763
From (Per Person)
A$2,094
Save 1,115
Per Person
View Trip
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