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Puerto Rico Cruises Starting In May 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in May 2026 or 2027, we have 14 unique cruise itineraries and 126 departures available, operated by three of the world's leading cruise lines departing in May.
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8 Days
15 Days
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$31,640pp
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14 Cruises (126 Cruise Departures)
8 Day Eastern Caribbean with St. Thomas From Fort Lauderdale with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Majestic Princess, Regal Princess, Sun Princess
Departures: Nov 2025 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Multiple Deals Available
Inside
$279
Oceanview
$349
Balcony
$599
Suite
$799
From
US$279
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Independence of the Seas, Wonder of the Seas
Departures: Nov 2025 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$407
Oceanview
$899
Balcony
$929
Suite
$1,578
From
US$407
Save 665
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,320
Oceanview
$1,391
Balcony
$1,534
Suite
$3,058
From
US$1,320
Save 962
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Nov 2025 to Oct 2027
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$394
Oceanview
$504
Balcony
$714
Suite
$1,424
From
US$394
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2026 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$905
Oceanview
$1,185
Balcony
$1,238
Suite
$1,903
From
US$905
Save 626
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Black Friday Sale
Inside
$534
Oceanview
$676
Balcony
$734
Suite
$1,099
From
US$534
Per Person
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departure: 02 May 2026
Visit: USA, Sint Maarten, Puerto Rico, Haiti
Exclusive Savings
Inside
$1,312
Oceanview
$1,412
Balcony
$1,801
Suite
$2,682
From
US$1,312
Save 744
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Aug 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Black Friday Sale
Inside
$1,130
Oceanview
$1,340
Balcony
$1,590
Suite
$2,305
From
US$1,130
Per Person
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departure: 03 May 2026
Visit: USA, Virgin Islands, Puerto Rico, Haiti
Exclusive Savings
Inside
$1,630
Oceanview
$1,729
Balcony
$1,830
Suite
$3,424
From
US$1,630
Save 805
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Aug 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Bahamas
Black Friday Sale
Inside
$1,188
Oceanview
$1,308
Balcony
$1,568
Suite
$2,293
From
US$1,188
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
Ship: Rhapsody of the Seas
Departure: 02 May 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Dominica
Exclusive Savings
Inside
$530
Oceanview
$600
Balcony
$1,881
Suite
$1,941
From
US$530
Save 411
Per Person
View Trip
9 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departure: 01 May 2026
Visit: USA, Virgin Islands, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$795
Oceanview
$1,145
Balcony
$1,387
Suite
$4,695
From
US$795
Save 433
Per Person
View Trip
10 Day Eastern Caribbean & Bermuda with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departures: May 2026 to Aug 2027
Visit: USA, Bermuda, Sint Maarten, Puerto Rico, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$977
Oceanview
$1,208
Balcony
$1,547
Suite
$2,112
From
US$977
Save 725
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Aug 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Black Friday Sale
Inside
$1,110
Oceanview
$1,340
Balcony
$1,500
Suite
$2,276
From
US$1,110
Per Person
View Trip
Results: 14 results

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