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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 12 unique cruise itineraries and 132 departures available, operated by four of the world's leading cruise lines departing in May.
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12 Cruises (132 Cruise Departures)
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
$1,261
Oceanview
$1,451
Balcony
$1,561
Suite
$3,312
From
US$1,261
Save 939
Per Person
View Trip
8 Day San Juan, St Kitts & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 29 May 2027
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,258
Oceanview
$1,338
Balcony
$1,481
Suite
$3,102
From
US$1,258
Save 666
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (4)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Coral Princess, Regal Princess
Departures: May 2026 to Dec 2026
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Princess Standard
Inside
$749
Oceanview
$1,040
Balcony
$909
Suite
$1,149
From
US$749
Per Person
View Trip
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
Departures: Mar 2026 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Princess Standard
Inside
$534
Oceanview
-
Balcony
$699
Suite
$939
From
US$534
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: Feb 2026 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$682
Oceanview
$802
Balcony
$1,024
Suite
$1,479
From
US$682
Save 647
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: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$574
Oceanview
$774
Balcony
$914
Suite
$1,434
From
US$574
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
Princess Standard
Inside
$494
Oceanview
$534
Balcony
$699
Suite
$859
From
US$494
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
Exclusive Savings
Inside
$835
Oceanview
$1,085
Balcony
$1,298
Suite
$2,483
From
US$835
Save 781
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
$720
Oceanview
$818
Balcony
$1,273
Suite
$1,369
From
US$783
Save 435
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
$689
Oceanview
$769
Balcony
$1,248
Suite
$1,423
From
US$689
Save 568
Per Person
View Trip
10 Day Bermuda & Eastern Caribbean 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 Jul 2026
Visit: USA, Bermuda, Sint Maarten, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,418
Oceanview
$1,838
Balcony
$2,151
Suite
$2,925
From
US$1,656
Save 823
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
$1,095
Oceanview
$1,495
Balcony
$2,350
Suite
$2,682
From
US$1,095
Save 562
Per Person
View Trip
Results: 12 results

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