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Cruises from Puerto Rico to Barbados

Are you looking for a cruise from Puerto Rico to Barbados? December is the most popular month to cruise between Puerto Rico and Barbados and there are 17 departures available from four of the world's leading cruise lines.
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21 Days
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$9,299pp
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13 Cruises (17 Cruise Departures)
15 Day Yachtsman's Caribbean In Depth with Seabourn
Cruise

15 Days (14 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 05 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Guadeloupe, Dominica, Saint Lucia
Exclusive DealBonus Onboard Credit
INSIDE
-
OCEANVIEW
-
BALCONY
$8,399
SUITE
$13,999
From (per person) 8,399
View Trip
8 Day Yachtsman's Caribbean with Seabourn
Cruise

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 05 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+3 more), Saint Vincent, Grenada, Barbados
Exclusive DealBonus Onboard Credit
INSIDE
-
OCEANVIEW
-
BALCONY
$4,299
SUITE
$7,499
From (per person) 4,299
View Trip
8 Day Southern Caribbean Voyage with Azamara Cruises
Cruise
 (3)

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departures: Nov 2025 to Dec 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
INSIDE
$2,219
OCEANVIEW
$2,769
BALCONY
$3,829
SUITE
$4,449
From (per person) 2,219
View Trip
8 Day Southern Caribbean Cruise: Antigua, Grenada & Barbados with Azamara Cruises
Cruise
 (3)

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2025 to Dec 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
INSIDE
$1,339
OCEANVIEW
$1,719
BALCONY
$2,309
SUITE
$3,739
From (per person) 1,339
View Trip
11 Day Southern Caribbean Cruise: Antigua, St. Barts & Martinique with Azamara Cruises
Cruise
 (1)

11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+4 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados
INSIDE
$2,079
OCEANVIEW
$2,409
BALCONY
$3,249
SUITE
$5,359
From (per person) 2,079
View Trip
9 Day Southern Caribbean Voyage with Azamara Cruises
Cruise
 (3)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+3 more), Saint Vincent, Trinidad and Tobago, Barbados
INSIDE
$2,229
OCEANVIEW
$2,299
BALCONY
$2,829
SUITE
-
From (per person) 2,229
View Trip
11 Day San Juan to Bridgetown with Silversea
Cruise

11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 06 February 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+7 more), Montserrat, Guadeloupe, Dominica, Martinique, Saint Lucia, Grenada, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$6,100
BALCONY
$7,200
SUITE
$10,400
From (per person) 6,100
View Trip
8 Day San Juan to Bridgetown with Silversea
Cruise

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 29 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Bonaire (+2 more), Curacao, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$4,400
BALCONY
$5,100
SUITE
$4,600
From (per person) 4,400
View Trip
21 Day Holiday Caribbean Enchantment with Seabourn
Cruise

21 Days (20 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+9 more), Martinique, Saint Vincent, Grenada, Barbados, Saint Lucia, Montserrat, Curacao, Aruba, Bonaire
Exclusive DealBonus Onboard Credit
INSIDE
-
OCEANVIEW
-
BALCONY
$9,299
SUITE
-
From (per person) 9,299
View Trip
21 Day Southern Caribbean Discovery with Seabourn
Cruise

21 Days (20 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 02 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+10 more), Martinique, Dominica, Montserrat, Saint Kitts and Nevis, Antigua and Barbuda, Virgin Islands, Guadeloupe, Saint Vincent, Grenada, Barbados
Exclusive DealBonus Onboard Credit
INSIDE
-
OCEANVIEW
-
BALCONY
$8,899
SUITE
$20,699
From (per person) 8,899
View Trip
17 Day An Extended Journey Of Bewitching Caribbean Gems with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+7 more), Anguilla, USA, Dominican Republic, Saint Kitts and Nevis, Martinique, Saint Vincent, Barbados
Mutiple Deals Available
INSIDE
-
OCEANVIEW
-
BALCONY
$5,585
SUITE
$6,485
From (per person) 5,585
View Trip
11 Day San Juan to Bridgetown with Silversea
Cruise

11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 10 January 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda (+7 more), Montserrat, Guadeloupe, Saint Kitts and Nevis, Martinique, Saint Lucia, Grenada, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$6,300
BALCONY
$7,400
SUITE
$10,700
From (per person) 6,300
View Trip
9 Day Yachtsman's Caribbean with Seabourn
Cruise

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+4 more), Martinique, Saint Vincent, Grenada, Barbados
Exclusive DealBonus Onboard Credit
INSIDE
-
OCEANVIEW
-
BALCONY
$3,799
SUITE
$7,999
From (per person) 3,799
View Trip
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