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Puerto Rico Cruises Starting In May 2027

If you're looking at joining a cruise to Puerto Rico in May 2027, we have 7 unique cruise itineraries and 97 departures available, operated by four of the world's leading cruise lines departing in May.
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7 Cruises (97 Cruise Departures)
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, Bahamas
Exclusive Savings
Inside
$1,382
Oceanview
$1,521
Balcony
$1,637
Suite
$3,434
From
US$1,382
Save 740
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
$559
Oceanview
$609
Balcony
$874
Suite
$1,069
From
US$559
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
$710
Oceanview
$920
Balcony
$1,273
Suite
$2,238
From
US$710
Save 669
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean 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
$1,396
Oceanview
$1,534
Balcony
$1,746
Suite
$2,729
From
US$1,396
Save 905
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: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$594
Oceanview
$798
Balcony
$857
Suite
$1,404
From
US$594
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
$766
Balcony
$1,248
Suite
$1,448
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
$1,218
Oceanview
$1,832
Balcony
$2,045
Suite
$3,539
From
US$1,782
Save 893
Per Person
View Trip
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