Filter Results
Departures
Duration
7 Days
22 Days
End City
Ship Features
Operators
Price
$1,000pp
$12,760pp
Countries
Filter Results
92 Cruises (255 Cruise Departures)
Cruise
A Journey From San Juan To Miami
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 29 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Dominican Republic, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$7,276
SUITE
$8,875
From 7,276
Cruise
Valiant Caribbean Holidays
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 20 December 2025
Countries Visited: Puerto Rico, Sint Maarten, Saint Kitts and Nevis, Antigua and Barbuda (+2 more), Saint Lucia, Virgin Islands
INSIDE
$2,501
OCEANVIEW
$2,807
BALCONY
$3,062
SUITE
$7,192
From 2,501
Cruise
Sunny Miles of Tropical Isles
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
Quaint Castries to Elegant Antigua
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
New ReleaseCruise
Quintessential Caribbean
8 Days (7 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Jan 2027 to Mar 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+2 more), Antigua and Barbuda, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,836
BALCONY
-
SUITE
$7,375
Cruise
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 17 January 2026
Exclusive Deal
INSIDE
$1,650
OCEANVIEW
$1,937
BALCONY
$2,243
SUITE
$3,518
Cruise
A Journey to Yacht-filled Harbours and Scenic Sail-ins
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Departures: Nov 2024 to Mar 2025
Countries Visited: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,420
SUITE
$6,272
From 5,420
Cruise
Cartagena, Aruba, Antigua & More
12 Days (11 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 February 2026
INSIDE
$3,497
OCEANVIEW
$3,930
BALCONY
$4,288
SUITE
$10,111
From 3,497
Cruise
A Journey From San Juan To Miami
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+1 more), USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,401
SUITE
$5,371
From 4,401
Cruise
Aruban Sights & Antiguan Nights
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 03 January 2026
INSIDE
$2,131
OCEANVIEW
$2,386
BALCONY
$2,616
SUITE
$6,120
From 2,131
Cruise
Southern Caribbean - San Juan
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Epic
Departure: 14 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+2 more), Saint Lucia, Saint Kitts and Nevis
INSIDE
$2,293
OCEANVIEW
-
BALCONY
$2,721
SUITE
$2,905
From 2,293
Cruise
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 30 November 2024
Countries Visited: Puerto Rico, Sint Maarten, Saint Lucia, Barbados (+2 more), Dominica, Antigua and Barbuda
Exclusive Offer
INSIDE
$1,393
OCEANVIEW
$1,502
BALCONY
$1,785
SUITE
$3,806
Cruise
Yachtsman's Caribbean
9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+4 more), Martinique, Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,056
SUITE
$9,853
From 5,056
Cruise
Antigua, Martinique, & Barbados & More
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 21 February 2026
Countries Visited: Puerto Rico, Sint Maarten, Barbados, Martinique (+2 more), Antigua and Barbuda, Virgin Islands
INSIDE
$2,240
OCEANVIEW
$2,496
BALCONY
$2,725
SUITE
$6,363
From 2,240
Cruise
Quintessential Caribbean Highlights
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
Cruise
Eternal Sunshine
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 30 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+2 more), Antigua and Barbuda, Saint Barthelemy
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
$5,334
BALCONY
$7,254
SUITE
$8,581
Cruise
Southern Caribbean Discovery
21 Days (20 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: 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
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$11,380
SUITE
$22,656
From 11,380
Cruise
Sunsets in the Lesser Antilles
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Departures: Jan 2025 to Mar 2026
INSIDE
$1,945
OCEANVIEW
$2,174
BALCONY
$2,393
SUITE
$5,265
From 1,945
Cruise
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departures: Oct 2024 to Dec 2024
Countries Visited: Puerto Rico, Sint Maarten, Antigua and Barbuda, Saint Lucia (+2 more), Barbados, Dominica
Exclusive Offer
INSIDE
$1,218
OCEANVIEW
$1,339
BALCONY
$1,793
SUITE
$3,782
Cruise
St. Lucia, St. Maarten, Barbados & More
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 13 December 2025
Countries Visited: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Dominica (+2 more), Barbados, Sint Maarten
INSIDE
$2,091
OCEANVIEW
$2,320
BALCONY
$2,550
SUITE
$5,948
From 2,091
Cruise
Virgin Island Views & Saint Isle Blues
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
Holiday Caribbean Enchantment
21 Days (20 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: 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
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$12,557
SUITE
$24,254
From 12,557
Cruise
A Journey From San Juan To Miami
10 Days (9 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Dominican Republic, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$9,935
SUITE
$12,118
From 9,935
New ReleaseCruise
Splendours of the Caribbean
7 Days (6 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 07 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$4,252
BALCONY
-
SUITE
$5,430
Cruise
Sun-Soaked Seas & Saint Isles
11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 22 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+4 more), Martinique, Barbados, Saint Lucia, Sint Maarten
INSIDE
$3,194
OCEANVIEW
$3,552
BALCONY
$3,908
SUITE
$9,186
From 3,194
Cruise
An Extended Journey of Caribbean Culture and Tropical Trails
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 21 February 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Trinidad and Tobago, Barbados, Saint Lucia, Martinique, Saint Vincent, Grenada
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$10,593
SUITE
$8,365
From 8,365
Cruise
An Extended Journey To Tropical Splendor
15 Days (14 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 29 November 2024
Countries Visited: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis (+5 more), Virgin Islands, USA, Dominica, Martinique, Barbados
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$11,682
SUITE
$14,256
From 11,682
Cruise
Treasures Of Aruba, Bonaire & Curacao
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
New ReleaseCruise
Caribbean Escapade
8 Days (7 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 21 November 2026
Countries Visited: Puerto Rico, Turks and Caicos Islands, Bahamas, USA
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,440
BALCONY
-
SUITE
$6,979
Cruise
Barefoot Reverie
11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 20 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$9,910
SUITE
$11,682
No Results found. Try changing your search filters.
