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Round-trip Cruises from San Juan

Are you looking for a cruise starting and ending in San Juan? December is the most popular month to join a roundtrip cruise from San Juan and we have 300 departures available from ten of the world's leading cruise lines.
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148 Cruises (300 Cruise Departures)
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: 13 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Martinique, Grenada
Princess Standard
Inside
$1,759
Oceanview
$2,029
Balcony
$2,619
Suite
$3,109
From
US$1,759
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
-
Oceanview
$1,183
Balcony
$1,393
Suite
$4,053
From
US$1,183
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
Departure: 20 December 2026
Visit: Puerto Rico, Aruba, Curacao, Virgin Islands
Exclusive Savings
Inside
$1,808
Oceanview
$2,002
Balcony
$2,099
Suite
$2,982
From
US$1,808
Save 51
Per Person
View Trip
17 Day An Extended Journey of Island Energy & Ocean Tranquillity with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visit: Puerto Rico, Saint Martin, Guadeloupe, Grenada (+7 more), Saint Lucia, Dominican Republic, USA, Virgin Islands, Anguilla, Martinique, Saint Kitts and Nevis
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,700
Suite
$8,960
From
US$7,700
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
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$485
Oceanview
$515
Balcony
$1,268
Suite
$1,292
From
US$485
Save 387
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights 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, Aruba, Curacao, Martinique, Saint Kitts and Nevis
With Love From the World
Inside
$833
Oceanview
$973
Balcony
$1,183
Suite
$3,493
From
US$833
Per Person
View Trip
9 Day Barbados, Dominica & St. Isle Spring with Virgin Voyages
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 March 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Dominica, Saint Martin
With Love From the World
Inside
$1,192
Oceanview
$1,432
Balcony
$1,672
Suite
$4,552
From
US$1,192
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
$769
Balcony
$1,248
Suite
$1,398
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: 14 November 2026
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
$643
Oceanview
$673
Balcony
$1,366
Suite
$1,551
From
US$643
Save 420
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: 26 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Montserrat
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,000
Balcony
$4,640
Suite
$9,700
From
US$4,000
Save 1,000
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
Exclusive Savings
Inside
-
Oceanview
$3,760
Balcony
$4,320
Suite
$8,980
From
US$3,760
Save 940
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
Departures: Jan 2028 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,240
Balcony
$4,880
Suite
$10,020
From
US$4,240
Save 1,060
Per Person
View Trip
12 Day Southern Caribbean Intensive with Celebrity Cruises
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Constellation
Departure: 17 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia (+5 more), Grenada, Barbados, Saint Vincent, Martinique, Dominica
Exclusive Savings
Inside
$1,097
Oceanview
$1,264
Balcony
$2,214
Suite
$7,380
From
US$1,097
Save 771
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
$604
Oceanview
$654
Balcony
$1,203
Suite
$1,181
From
US$604
Save 461
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
$657
Oceanview
$812
Balcony
$989
Suite
-
From
US$657
Save 548
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 Constellation
Departure: 09 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Grenada
Exclusive Savings
Inside
$849
Oceanview
$896
Balcony
$1,091
Suite
$3,497
From
US$849
Save 625
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 25 April 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$874
Oceanview
$874
Balcony
$1,054
Suite
-
From
US$874
Save 530
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 Dawn
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,520
Balcony
$4,320
Suite
$8,500
From
US$3,520
Save 880
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 Constellation
Departure: 06 February 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Lucia, Grenada
Exclusive Savings
Inside
$818
Oceanview
$863
Balcony
$1,006
Suite
$3,090
From
US$818
Save 615
Per Person
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Nov 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy, Montserrat, Antigua and Barbuda, Guadeloupe
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,667
Balcony
-
Suite
$15,208
From
US$11,667
Save 12,828
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: 28 November 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Grenada
Exclusive Savings
Inside
$482
Oceanview
$532
Balcony
$807
Suite
$2,507
From
US$482
Save 406
Per Person
View Trip
15 Day An Extended Journey Through Golden Shores & Island Grace with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy (+4 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Guadeloupe
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,545
Suite
$7,525
From
US$6,545
Per Person
View Trip
16 Day An Extended Journey into Island Bliss & Lively Celebrations with Explora Journeys
Cruise

16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Saint Barthelemy, Anguilla, USA, Dominican Republic
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$10,050
Suite
$10,835
From
US$10,050
Per Person
View Trip
11 Day A Journey Into Historic Charm & Tropical Bliss with Explora Journeys
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 February 2026
Visit: Puerto Rico, Aruba, Curacao, Bonaire (+4 more), Barbados, Guadeloupe, Saint Martin, Virgin Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,495
Suite
$6,195
From
US$5,495
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: 12 December 2027
Visit: Puerto Rico, Saint Vincent, Barbados, Martinique, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$482
Oceanview
$532
Balcony
$807
Suite
$2,507
From
US$482
Save 407
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
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,351
Balcony
-
Suite
$7,121
From
US$5,351
Save 7,639
Per Person
View Trip
8 Day Southern Caribbean Holiday with Celebrity Cruises
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departures: Nov 2027 to Dec 2027
Visit: Puerto Rico, Dominica, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
$484
Oceanview
$534
Balcony
$809
Suite
$2,509
From
US$484
Save 574
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 Dawn
Departure: 21 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,680
Balcony
$4,240
Suite
$8,560
From
US$3,680
Save 920
Per Person
View Trip
Results: 121-148 of 148

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