Home > Cruises > Caribbean Cruises > Round-trip Cruises from San Juan

Round-trip Cruises from San Juan

Are you looking for a cruise starting and ending in San Juan? January is the most popular month to join a roundtrip cruise from San Juan and we have 315 departures available from ten of the world's leading cruise lines.
Filter Results
Departures
Show More...
Duration
6 Days
25 Days
Ship Size
Ship Features
Operators
Show More...
Price
$300pp
$24,980pp
Countries
Show More...
Filter Results
154 Cruises (315 Cruise Departures)
11 Day West Indies Explorer with Viking Cruises
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ships: Viking Sea, Viking Sky
Departures: Mar 2026 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Viking $799 Air Deal
Viking $699 Air Deal
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
Per Person
View Trip
15 Day Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia with Azamara Cruises
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 21 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Exclusive Savings
Inside
$3,507
Oceanview
$4,486
Balcony
$5,505
Suite
$8,085
From
US$3,507
Save 82
Per Person
View Trip
25 Day An Extended Journey into Island Elegance & Mysteries of the Amazon with Explora Journeys
Cruise

25 Days (24 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 February 2027
Visit: Puerto Rico, Saint Barthelemy, Martinique, Barbados (+6 more), Trinidad and Tobago, Brazil, French Guiana, Saint Vincent, Saint Lucia, Saint Kitts and Nevis
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$17,590
Suite
$18,360
From
US$17,590
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 February 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Dominica, Barbados
Princess Standard
Inside
$499
Oceanview
$599
Balcony
$1,135
Suite
$1,099
From
US$499
Per Person
View Trip
7 Day Caribbean East: Virgin & Saint Isles with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
With Love From the World
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,540
From
US$834
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (6)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 17 January 2027
Visit: Puerto Rico, Barbados, Grenada, Saint Lucia, Antigua and Barbuda, Saint Martin
Princess Standard
Inside
$927
Oceanview
$1,022
Balcony
$1,287
Suite
$1,777
From
US$927
Per Person
View Trip
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 20 February 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Grenada, Curacao, Aruba
Exclusive Savings
Inside
$770
Oceanview
-
Balcony
-
Suite
-
From
US$770
Save 512
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 22 March 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Barbados
Exclusive Savings
Inside
$719
Oceanview
$759
Balcony
$917
Suite
$1,830
From
US$719
Save 443
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola with Princess
Cruise
 (6)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$1,037
Oceanview
$1,112
Balcony
$1,227
Suite
$1,727
From
US$1,037
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 16 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Barbados, Saint Lucia, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,659
Oceanview
$1,909
Balcony
$2,559
Suite
$3,009
From
US$1,659
Per Person
View Trip
11 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 01 February 2026
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao, Bonaire, Barbados, Saint Vincent
Exclusive Savings
Inside
$999
Oceanview
-
Balcony
-
Suite
-
From
US$999
Save 533
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: Jewel of the Seas
Departures: Feb 2026 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Dominica, Barbados
Exclusive Savings
Inside
$589
Oceanview
$639
Balcony
$899
Suite
$1,520
From
US$589
Save 525
Per Person
View Trip
11 Day San Juan to San Juan with Silversea
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 11 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy (+5 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Inside
-
Oceanview
$4,700
Balcony
$5,400
Suite
$9,000
From
US$4,700
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (6)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 10 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados, Grenada
Princess Standard
Inside
$1,946
Oceanview
$2,135
Balcony
$2,606
Suite
$3,343
From
US$1,946
Per Person
View Trip
8 Day Southern Caribbean Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 14 November 2027
Visit: Puerto Rico, Saint Vincent, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$594
Oceanview
$644
Balcony
$919
Suite
$2,619
From
US$700
Save 287
Per Person
View Trip
8 Day Saint (Isles) & Seas of the Caribbean with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 06 March 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
With Love From the World
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
Per Person
View Trip
16 Day An Extended Journey Of Caribbean Inspiration And Island Beauty with Explora Journeys
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 January 2026
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Antigua and Barbuda (+6 more), Anguilla, USA, Guadeloupe, Barbados, Martinique, Saint Kitts and Nevis
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$10,305
Suite
$14,630
From
US$10,305
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Mar 2026 to Mar 2026
Visit: Puerto Rico, Virgin Islands, Curacao, Aruba, Bonaire
Exclusive Savings
Inside
$697
Oceanview
$778
Balcony
$1,050
Suite
$1,924
From
US$697
Save 510
Per Person
View Trip
8 Day Barbados, Antigua, BVI & More with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 24 January 2026
Visit: Puerto Rico, Virgin Islands, Barbados, Martinique, Antigua and Barbuda, Sint Maarten
With Love From the World
Inside
$1,970
Oceanview
$1,272
Balcony
-
Suite
$2,793
From
US$1,272
Per Person
View Trip
15 Day Southern Caribbean Adventurer Holiday with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,919
Oceanview
$2,219
Balcony
$2,919
Suite
$3,317
From
US$1,919
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 09 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,669
Oceanview
$1,919
Balcony
$2,569
Suite
$3,019
From
US$1,669
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: 27 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$710
Oceanview
$770
Balcony
$1,320
Suite
$1,430
From
US$1,060
Save 50
Per Person
View Trip
8 Day Valiant's Haunted Halloween Soiree with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
With Love From the World
Inside
$973
Oceanview
$1,183
Balcony
$1,393
Suite
$4,200
From
US$973
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 20 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+5 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Princess Standard
Inside
$1,759
Oceanview
$2,029
Balcony
$2,619
Suite
$3,009
From
US$1,759
Per Person
View Trip
8 Day Sunny Miles of Tropical Isles with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Feb 2026 to Jan 2027
Visit: Puerto Rico, Sint Maarten, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
With Love From the World
Inside
$903
Oceanview
$1,043
Balcony
$1,253
Suite
$3,493
From
US$903
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, St. Lucia & St. Kitts with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Dec 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin
Azamara Always Included
Exclusive Savings
Inside
$3,413
Oceanview
$3,938
Balcony
$5,170
Suite
$7,924
From
US$3,413
Save 78
Per Person
View Trip
8 Day Southern Caribbean Cruise San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 14 February 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Kitts and Nevis, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$3,263
From
US$3,263
Save 96
Per Person
View Trip
8 Day Saint Isles & The Greater Antilles with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 20 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Lucia, Barbados, Dominica, Saint Martin
With Love From the World
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
Per Person
View Trip
8 Day Sunsets in the Lesser Antilles with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Mar 2026 to Apr 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Martinique, Curacao, Aruba
With Love From the World
Inside
$833
Oceanview
$903
Balcony
$1,113
Suite
$3,493
From
US$833
Per Person
View Trip
8 Day Southern Caribbean with Barbados and Tortola with Princess
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Princess Standard
Inside
$750
Oceanview
$859
Balcony
$1,150
Suite
$1,500
From
US$750
Per Person
View Trip
Results: 1-30 of 154

No results found. Try amending 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

Festivals & Events Luxury Cruises Short Cruise Breaks Wildlife Cruises

Countries

Aruba Bahamas Barbados Belize Canada Cayman Islands China Colombia Curacao Dominican Republic Haiti Honduras Jamaica Mexico Panama Puerto Rico Saint Barthelemy Saint Lucia Saint Martin Singapore Turks and Caicos Islands USA Vietnam Virgin Islands

Cities

Cruises from San Juan Cruises from San Juan Cruises from San Juan

Routes

Cruises from La Romana to La Romana Cruises from Miami to San Juan Cruises from San Juan to Miami Cruises from San Juan to San Juan

Country Routes

Cruises from Puerto Rico to USA Cruises from Dominican Republic to USA Cruises from USA to Puerto Rico Cruises from USA to Dominican Republic

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