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Puerto Rico Luxury Cruises

Explore Puerto Rico on one of 53 luxury cruises, departing from Barcelona, Bridgetown, Lisbon, Malaga, Miami and more. December is the most popular month to cruise to Puerto Rico and we have over 56 departures available from six of the world's leading cruise lines specialising in luxury cruises.
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6 Days
23 Days
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$28,798pp
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53 Cruises (56 Cruise Departures)
10 Day A Journey Through Caribbean Delights & Wildlife Wonders with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 19 February 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Anguilla
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,960
Suite
$6,560
From
US$5,960
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
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$5,245
Oceanview
$5,973
Balcony
$8,252
Suite
$11,405
From
US$5,245
Save 5,453
Per Person
View Trip
8 Day A Journey of Intimate Island Bliss & Caribbean Breeze with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 February 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,180
Suite
$4,820
From
US$4,180
Per Person
View Trip
8 Day Eastern Caribbean Cruise: Barbados, Saint Kittsand Nevis & Puerto Rico with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 07 December 2027
Visit: Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico, USA
Azamara Always Included
Inside
$1,809
Oceanview
$2,178
Balcony
$2,750
Suite
$4,040
From
US$1,809
Per Person
View Trip
8 Day A Journey of Salsa Beats, Spectacular Fireworks & Dominican Charm with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 30 December 2027
Visit: Puerto Rico, Virgin Islands, Dominican Republic, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,690
Suite
$6,620
From
US$5,690
Per Person
View Trip
8 Day Caribbean Yachting Discovery with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Saint John's to San Juan
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia
Departures: Feb 2026 to Mar 2028
Visit: Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Virgin Islands, Puerto Rico
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$4,787
Balcony
-
Suite
$4,816
From
US$4,816
Save 7,412
Per Person
View Trip
16 Day Fall Caribbean Passage with Oceania Cruises
Cruise
 (3)

16 Days (15 Nights) Barcelona to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 25 November 2026
Visit: Spain, Portugal, Puerto Rico, Dominican Republic, USA
Your World Inclusions
Upgrade Your Experience
Exclusive Savings
Inside
$3,622
Oceanview
$4,398
Balcony
$4,239
Suite
$5,394
From
US$3,622
Save 3,776
Per Person
View Trip
8 Day A Journey Across Oceanic Gems & The Unresistible Caribbean Charm with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 March 2028
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,415
From
US$3,915
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
8 Day A Journey Through Balmy Shores & Stirring Scenery with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 April 2027
Visit: Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,920
Suite
$4,520
From
US$3,920
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 Fare
Exclusive Savings
Inside
-
Oceanview
$4,080
Balcony
$4,640
Suite
$8,880
From
US$4,080
Save 1,020
Per Person
View Trip
17 Day A Grand Journey From Atlantic Exploration To Mediterranean Delights with Explora Journeys
Cruise

17 Days (16 Nights) Miami to Barcelona
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 08 March 2027
Visit: USA, Puerto Rico, Saint Martin, Portugal, Spain
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,990
Suite
$9,040
From
US$7,990
Per Person
View Trip
8 Day A Journey into Tropical Utopia & Art Deco Flair with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 02 March 2026
Visit: Puerto Rico, Antigua and Barbuda, Anguilla, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,825
Suite
$4,310
From
US$3,825
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 27 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,303
Balcony
-
Suite
$7,073
From
US$5,303
Save 7,687
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 07 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$3,563
Balcony
-
Suite
$4,921
From
US$3,563
Save 5,827
Per Person
View Trip
8 Day A Journey Through The Caribbean's Rich History & Palm-shaded Paradise with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Dominican Republic, USA, Bahamas
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
8 Day A Journey Through Art Deco Wonders & Caribbean Adventures with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 23 December 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,745
Suite
$5,545
From
US$4,745
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Saint Vincent
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,920
Balcony
$4,620
Suite
$9,660
From
US$3,920
Save 1,680
Per Person
View Trip
15 Day San Juan to Lisbon with Silversea
Cruise

15 Days (14 Nights) San Juan to Lisbon
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 09 March 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Spain, Portugal
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,300
Balcony
$3,900
Suite
$9,880
From
US$3,300
Save 2,200
Per Person
View Trip
8 Day A Journey From Glorious Shorelines To Nature's Allure with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 March 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,920
Suite
$4,520
From
US$3,920
Per Person
View Trip
8 Day A Journey From Glorious Shorelines To Nature's Allure with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 February 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,720
Suite
$5,440
From
US$4,720
Per Person
View Trip
11 Day Caribbean Splendor with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 02 February 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,977
Suite
$7,014
From
US$4,977
Save 5,221
Per Person
View Trip
15 Day Discover Island Rhythms & Coastal Dreams with Emerald Cruises
Cruise

15 Days (14 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Turks and Caicos Islands, Bahamas, USA
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$12,492
Balcony
-
Suite
$16,033
From
US$12,492
Save 13,188
Per Person
View Trip
Results: 31-53 of 53

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Travel Styles

Luxury Cruises

Trip Lengths

10 Day 2 Week 7 Day

Departure Months

February March October November December January April

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

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