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Puerto Rico Cruises Starting In November 2026 and 2027

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51 Cruises (193 Cruise Departures)
16 Day Canaries To The Caribbean with Oceania Cruises
Cruise
 (1)

16 Days (15 Nights) Lisbon to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 09 November 2026
Visit: Portugal, Spain, Puerto Rico, Bahamas, USA
Your World Inclusions
Exclusive Savings
Inside
$2,275
Oceanview
$2,600
Balcony
$3,597
Suite
$4,853
From
US$2,275
Save 4,723
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 29 November 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$666
Oceanview
-
Balcony
$826
Suite
$901
From
US$666
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 20 November 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Limited Time Offer
Inside
$953
Oceanview
$1,193
Balcony
$1,433
Suite
$3,920
From
US$953
Per Person
View Trip
8 Day Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departures: Nov 2027 to Dec 2027
Visit: Puerto Rico, Aruba, Barbados, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,419
Oceanview
$1,619
Balcony
$1,817
Suite
$2,690
From
US$1,419
Save 52
Per Person
View Trip
9 Day Eastern Caribbean with Tortola with Princess
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departure: 27 November 2027
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Princess Standard
Inside
$699
Oceanview
-
Balcony
$804
Suite
$1,549
From
US$699
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 28 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$833
Oceanview
$973
Balcony
$1,183
Suite
$3,983
From
US$833
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
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 08 November 2026
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Bahamas
Limited Time Offer
Inside
$1,192
Oceanview
$1,432
Balcony
$1,592
Suite
$3,912
From
US$1,192
Per Person
View Trip
8 Day Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departure: 28 November 2027
Visit: Puerto Rico, Aruba, Curacao, Saint Martin, Saint Kitts and Nevis
Inside
$1,119
Oceanview
$1,319
Balcony
$1,569
Suite
$2,399
From
US$1,119
Per Person
View Trip
23 Day Flamenco To Flamingos with Oceania Cruises
Cruise
 (1)

23 Days (22 Nights) Barcelona to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 02 November 2026
Visit: Spain, Portugal, Puerto Rico, Bahamas, USA
Your World Inclusions
Your World Included Credit
Exclusive Savings
Inside
$5,536
Oceanview
$5,973
Balcony
$8,398
Suite
$11,550
From
US$5,536
Save 5,762
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,209
Oceanview
$1,409
Balcony
$1,659
Suite
$2,487
From
US$1,209
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$619
Oceanview
-
Balcony
$924
Suite
$1,169
From
US$619
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 14 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia, Saint Kitts and Nevis
Limited Time Offer
Inside
$1,014
Oceanview
$1,134
Balcony
$1,314
Suite
$3,294
From
US$1,014
Per Person
View Trip
8 Day A Journey Across the Caribbean’s Colourful Heart with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 13 November 2027
Visit: Puerto Rico, Virgin Islands, Dominican Republic, USA, Bahamas
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
Per Person
View Trip
8 Day Southern Caribbean with Curacao with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 14 November 2027
Visit: USA, Jamaica, Aruba, Curacao, Puerto Rico
Princess Standard
Inside
$729
Oceanview
$849
Balcony
$1,124
Suite
$1,699
From
US$729
Per Person
View Trip
9 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departure: 07 November 2026
Visit: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Turks and Caicos Islands
Exclusive Savings
Inside
$1,264
Oceanview
$2,073
Balcony
$2,476
Suite
$3,601
From
US$1,264
Save 673
Per Person
View Trip
11 Day Miami to Miami with Silversea
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 30 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis
All-Inclusive Fare
Inside
-
Oceanview
$6,000
Balcony
$6,900
Suite
$10,300
From
US$6,000
Per Person
View Trip
15 Day Lisbon to San Juan with Silversea
Cruise

15 Days (14 Nights) Lisbon to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 27 November 2027
Visit: Portugal, Spain, Cape Verde, Saint Barthelemy, Puerto Rico
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,200
Balcony
$4,700
Suite
$9,900
From
US$4,200
Save 1,500
Per Person
View Trip
11 Day Caribbean Cruise From Jacksonville To Jacksonville with Norwegian Cruise Line
Cruise

11 Days (10 Nights) Jacksonville to Jacksonville
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Dawn
Departure: 29 November 2027
Visit: USA, Bahamas, Dominican Republic, Virgin Islands, Puerto Rico
Inside
$1,139
Oceanview
$1,369
Balcony
$1,937
Suite
$2,325
From
US$1,139
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Inside
$789
Oceanview
$949
Balcony
$1,024
Suite
$1,399
From
US$789
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departures: Nov 2026 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$673
Oceanview
$694
Balcony
$1,164
Suite
$1,276
From
US$673
Save 460
Per Person
View Trip
Results: 31-51 of 51

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