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Departures
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$1,600pp
$37,350pp
Countries
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363 Cruises (520 Cruise Departures)
Cruise
Bridgetown to Cartagena
10 Days (9 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 05 March 2026
Countries Visited: Aruba, Barbados, Colombia, Netherlands Antilles (+2 more), Saint Vincent, Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,603
BALCONY
$10,296
SUITE
$15,048
From 9,603
Cruise
Caribbean Illumination
11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departures: Feb 2026 to Apr 2026
Countries Visited: USA, Puerto Rico, Saint Kitts and Nevis, Saint Lucia (+2 more), Dominica, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,190
SUITE
$9,942
Cruise
History and Culture Visiting Caribbean Jewels
8 Days (7 Nights) Marigot to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departures: Mar 2025 to Apr 2025
Countries Visited: Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Guadeloupe
Exclusive Savings
INSIDE
-
OCEANVIEW
$10,526
BALCONY
$14,162
SUITE
$15,200
Cruise
Caribbean Sea Harbors
22 Days (21 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departure: 01 February 2025
Countries Visited: Barbados, Curacao, Bonaire, Aruba (+9 more), Colombia, Dominican Republic, Antigua and Barbuda, Martinique, Saint Lucia, Guadeloupe, Virgin Islands, Saint Kitts and Nevis, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$17,438
SUITE
$32,837
From 17,438
Cruise
Cartagena to New York
11 Days (10 Nights) Cartagena to New York
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 08 June 2024
Countries Visited: Aruba, Colombia, USA, Virgin Islands
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
$5,494
BALCONY
$7,276
SUITE
-
From 5,494
Cruise
Bridgetown to Bridgetown
8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 19 January 2026
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,811
BALCONY
$10,494
SUITE
$9,306
From 8,811
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
Maya To Island Heritage
13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 04 January 2026
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,628
SUITE
$12,172
Cruise
Merriment & Joy In The Tropics
13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 22 December 2025
Countries Visited: USA, Saint Kitts and Nevis, Antigua and Barbuda, Martinique (+4 more), Barbados, Grenada, Saint Lucia, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,765
SUITE
$11,399
Cruise
A Journey To Sainted Shores And Volcanic Islands
8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 13 December 2024
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,192
SUITE
$7,529
From 6,192
Cruise
A Journey From Miami To San Juan
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 22 December 2025
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,816
SUITE
$8,286
From 6,816
Cruise
Festive Caribbean
15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 22 December 2024
Countries Visited: USA, Jamaica, Aruba, Curacao (+6 more), Saint Vincent, Barbados, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Deal
INSIDE
$6,611
OCEANVIEW
$7,225
BALCONY
$9,670
SUITE
$13,462
Cruise
A Journey Of Wild Isles And Charmed Creole Harbours
8 Days (7 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 06 December 2024
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,192
SUITE
$7,529
From 6,192
Cruise
Dutch Isles Delights
13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 09 March 2026
Countries Visited: USA, Aruba, Curacao, Grenada (+3 more), Saint Vincent, Martinique, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,479
SUITE
$12,013
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
Cartagena to Bridgetown
10 Days (9 Nights) Cartagena to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 01 December 2025
Countries Visited: Colombia, Aruba, Bonaire, Curacao (+3 more), Saint Lucia, Saint Vincent, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,009
BALCONY
$9,504
SUITE
$14,058
From 9,009
Cruise
Philipsburg to Bridgetown
8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departures: Jan 2026 to Feb 2026
Countries Visited: Saint Martin, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Grenada, Martinique, Saint Vincent, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,910
BALCONY
$9,504
SUITE
$12,078
From 8,910
Cruise
Paradise Awaits
11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 14 November 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,475
SUITE
$10,436
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
Cruise
Island Rhythm & Coastal Charm
22 Days (21 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 20 December 2025
Countries Visited: USA, Aruba, Bonaire, Curacao (+8 more), Grenada, Saint Lucia, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$17,322
SUITE
$20,570
Cruise
A Journey To Barefoot Beaches And Colonial Plantations
8 Days (7 Nights) Bridgetown to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 February 2025
Countries Visited: Barbados, Saint Lucia, Martinique, Saint Vincent (+3 more), Trinidad and Tobago, Grenada, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,782
SUITE
$6,692
From 5,782
Cruise
An Extended Journey Of Caribbean Indulgence And Island Adventures
15 Days (14 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 February 2025
Countries Visited: Barbados, Saint Lucia, Martinique, Saint Vincent (+8 more), Trinidad and Tobago, Grenada, Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$10,593
SUITE
$12,276
From 10,593
Cruise
Turquoise Shores, Hidden Isles
11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
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
New ReleaseCruise
Vibes of the Virgin Islands
8 Days (7 Nights) Saint Thomas to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Dec 2026 to Mar 2027
Countries Visited: Virgin Islands, Saint Martin, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,440
BALCONY
-
SUITE
$6,979
Cruise
Holiday Havens
15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 21 December 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+6 more), Grenada, Barbados, Saint Vincent, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,460
SUITE
$16,083
Cruise
Champagne, Confetti & The Caribbean
11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 28 December 2024
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,357
SUITE
$11,396
Cruise
Bridgetown to Bridgetown
8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departures: Jan 2026 to Feb 2026
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,613
BALCONY
$9,999
SUITE
$9,108
From 8,613
New ReleaseCruise
Discover the Hidden Treasures of the Caribbean
22 Days (21 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara
Departures: Dec 2024 to Feb 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+6 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin, Virgin Islands, Bonaire
Exclusive Deal
INSIDE
-
OCEANVIEW
$13,548
BALCONY
-
SUITE
$16,974
Cruise
Sun-splashed Shores
8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 07 November 2024
Countries Visited: USA, Honduras, Belize, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$7,324
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