Home > Cruises > Caribbean Cruises > Cruises Starting and Ending in San Juan

Cruises Starting and Ending in 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 229 departures available from ten of the world's leading cruise lines.
Filter Results
Departures
Show More...
Duration
8 Days
15 Days
Ship Size
Ship Features
Operators
Show More...
Price
$1,000pp
$15,995pp
Countries
Show More...
Filter Results
71 Cruises (229 Cruise Departures)
Cruise

13 Days (12 Nights) San Juan to San Juan
Cruise Line: Seabourn
Ship: Ovation
Departure: 02 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Martinique, Dominica, Montserrat, Saint Kitts and Nevis, Antigua and Barbuda, Virgin Islands
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$7,585
SUITE
$15,243
From 7,585
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 27 December 2025
Countries Visited: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Saint Lucia (+2 more), Barbados, Virgin Islands
INSIDE
$3,111
OCEANVIEW
$3,468
BALCONY
$3,801
SUITE
$9,050
From 3,111
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Sint Maarten, Barbados, Saint Lucia (+2 more), Martinique, Saint Kitts and Nevis
INSIDE
$2,093
OCEANVIEW
$2,322
BALCONY
$2,552
SUITE
$5,950
From 2,093
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departures: Nov 2025 to Apr 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+1 more), Barbados
Exclusive Deal
INSIDE
$1,363
OCEANVIEW
$1,535
BALCONY
$2,011
SUITE
$2,972
Save 787
From 1,189
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Vincent (+1 more), Saint Kitts and Nevis
INSIDE
$2,127
OCEANVIEW
$2,382
BALCONY
$2,612
SUITE
$6,116
From 2,127
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Departure: 03 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive DealExclusive Solo Offer
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$10,059
SUITE
$11,544
Save 4,316
From 7,554
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departure: 17 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Martinique (+1 more), Barbados
Exclusive Deal
INSIDE
$1,643
OCEANVIEW
$1,931
BALCONY
$2,249
SUITE
$3,478
Save 660
From 1,436
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Departures: Oct 2024 to Dec 2024
Countries Visited: Puerto Rico, Sint Maarten, Antigua and Barbuda, Saint Lucia (+2 more), Barbados, Dominica
Exclusive Offer
INSIDE
$1,385
OCEANVIEW
$1,435
BALCONY
$1,834
SUITE
$3,782
Save 4,084
From 1,385
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 07 March 2026
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Martinique (+2 more), Antigua and Barbuda, Virgin Islands
INSIDE
$2,231
OCEANVIEW
$2,487
BALCONY
$2,716
SUITE
$6,354
From 2,231
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 02 December 2025
Countries Visited: Puerto Rico, Colombia, Curacao, Aruba (+3 more), Martinique, Antigua and Barbuda, Sint Maarten
INSIDE
$3,346
OCEANVIEW
$3,729
BALCONY
$4,087
SUITE
$9,604
From 3,346
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 January 2026
Countries Visited: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Antigua and Barbuda (+4 more), Martinique, Saint Lucia, Saint Vincent, Barbados
INSIDE
$3,068
OCEANVIEW
$3,451
BALCONY
$3,758
SUITE
$8,834
From 3,068
Results: 61-71 of 71

No Results found. Try changing your search filters.

Caribbean & Bahamas Cruises