Home > Cruises > Caribbean Cruises > Puerto Rico > May

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 15 unique cruise itineraries and 140 departures available, operated by four of the world's leading cruise lines departing in May.
Filter Results
Departures
Duration
8 Days
15 Days
Start & End Cities
Ship Size
Operators
Price
$400pp
$28,798pp
Countries
Show More...
Filter Results
15 Cruises (140 Cruise Departures)
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
$747
Oceanview
$1,074
Balcony
$1,222
Suite
$2,665
From
US$747
Save 759
Per Person
View Trip
8 Day Eastern Caribbean with St. Thomas From Fort Lauderdale with Princess
Cruise
 (8)

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
$564
Oceanview
-
Balcony
$739
Suite
$1,074
From
US$564
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
$729
Oceanview
$1,020
Balcony
$849
Suite
$1,224
From
US$729
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
$524
Oceanview
$524
Balcony
$749
Suite
$836
From
US$524
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: Mar 2026 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$682
Oceanview
$782
Balcony
$1,035
Suite
$1,509
From
US$682
Save 704
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: Mar 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$644
Oceanview
$894
Balcony
$894
Suite
$1,434
From
US$644
Save 52
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
$1,424
Oceanview
$1,532
Balcony
$1,612
Suite
$3,081
From
US$1,424
Save 766
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
Princess Standard
Inside
$1,030
Oceanview
$1,140
Balcony
$1,567
Suite
$2,129
From
US$1,030
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
$1,331
Oceanview
$1,451
Balcony
$1,561
Suite
$2,904
From
US$1,331
Save 999
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
$1,575
Oceanview
$1,463
Balcony
$1,903
Suite
$2,925
From
US$1,463
Save 985
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
Princess Standard
Inside
$1,032
Oceanview
$1,680
Balcony
$2,684
Suite
-
From
US$1,032
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
$1,473
From
US$689
Save 568
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
-
Oceanview
$988
Balcony
$1,273
Suite
$1,358
From
US$1,461
Save 50
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
$1,166
Oceanview
$1,245
Balcony
$2,058
Suite
-
From
US$1,166
Save 592
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
Princess Standard
Inside
$1,040
Oceanview
$1,106
Balcony
$1,616
Suite
$3,442
From
US$1,040
Per Person
View Trip
Results: 15 results

No trips found. Try adjusting the search filters.




Cruises found! Scroll up to view.

Caribbean & Bahamas Cruises

Aruba Cruises Bahamas Cruises Barbados Cruises Bermunda Cruises Caribbean Cruises Central America Cruises Jamaica Cruises Mexico Cruises Panama Cruises Puerto Rico Cruises Virgin Islands Cruises

Travel Styles

Luxury Cruises

Trip Lengths

10 Day 2 Week 7 Day

Departure Months

March April May June July August September October November December January February

Cities

San Juan

Routes

San Juan to San Juan

Country Routes

Puerto Rico to USA USA to Puerto Rico

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

© 2010-2026. Global Journeys. You're viewing our site in US dollars.

    

About Us | View Your Booking | Operators | Terms & Conditions | Site Map | We're hiring!

Global Journeys Travel Inc. is a Member of the American Society of Travel Advisors (ASTA No: 900374670), CLIA (No. 00046729) & is TICO Accredited (No. 50027921).

Travel Industry Associations