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Departures
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$1,600pp
$37,350pp
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363 Cruises (523 Cruise Departures)
Cruise
Radiant Island Dawns
13 Days (12 Nights) Miami to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 15 January 2026
Countries Visited: USA, Aruba, Curacao, Trinidad and Tobago (+6 more), Grenada, Saint Lucia, Saint Vincent, Dominica, Martinique, Barbados
Exclusive Deal
INSIDE
$5,826
OCEANVIEW
$6,361
BALCONY
$8,262
SUITE
$10,667
Cruise
Antillean Adventure
13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 27 March 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,609
SUITE
$11,846
Cruise
Iridescent Isles & Inlets
19 Days (18 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 19 February 2025
Countries Visited: USA, Saint Barthelemy, Saint Lucia, Grenada (+6 more), Barbados, Dominica, Antigua and Barbuda, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$12,092
SUITE
$16,379
Cruise
Enchantment Of The Lesser Antilles
18 Days (17 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 23 November 2024
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+8 more), Saint Kitts and Nevis, Grenada, Saint Vincent, Dominica, Aruba, Curacao, Bonaire, Trinidad and Tobago
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$12,975
SUITE
$19,959
From 12,975
Cruise
A Journey of Caribbean Islands from Clouds to Emeralds
9 Days (8 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 December 2025
Countries Visited: Barbados, Saint Vincent, Trinidad and Tobago, Martinique (+3 more), Montserrat, Virgin Islands, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$5,381
SUITE
$6,569
From 5,381
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
Willemstad to Bridgetown
10 Days (9 Nights) Willemstad to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 12 December 2024
Countries Visited: Antigua and Barbuda, Barbados, Netherlands Antilles, Saint Kitts and Nevis (+4 more), Saint Vincent, Trinidad and Tobago, Virgin Islands, Saint Lucia
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$13,860
From 13,860
Cruise
Cruising the Caribbean's Windward Islands - with Smithsonian Journeys
9 Days (8 Nights) Vieux Fort to Vieux Fort
Cruise Line: Ponant
Ship: Le Champlain
Departure: 30 January 2025
Exclusive Savings
INSIDE
$14,682
OCEANVIEW
$7,813
BALCONY
$9,812
SUITE
-
Cruise
A Journey from Miami to San Juan
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Nov 2024 to Feb 2025
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,158
SUITE
$6,272
From 5,158
Cruise
A Journey Meandering Amongst Lush Leewards Islands
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 03 March 2026
Countries Visited: Puerto Rico, Saint Martin, Guadeloupe, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$5,658
SUITE
$6,905
From 5,658
Cruise
Elegant Caribbean
13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 16 January 2026
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Guadeloupe, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,627
SUITE
$12,172
Cruise
Rhythm Of Paradise
12 Days (11 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 11 December 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+3 more), Martinique, Antigua and Barbuda, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,883
SUITE
$10,358
Cruise
A Journey from San Juan to Bridgetown
8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 21 February 2025
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,158
SUITE
$6,272
From 5,158
Cruise
Exotic Caribbean In Depth
15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Feb 2025
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Virgin Islands, Saint Kitts and Nevis, Sint Maarten, Martinique, Saint Vincent, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$11,121
SUITE
$20,630
From 11,121
Cruise
Champagne Colored Sands
11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 13 February 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,653
SUITE
$11,247
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
A Journey From Miami To Miami
10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 February 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Antigua and Barbuda (+1 more), Virgin Islands
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,049
SUITE
$7,385
From 6,049
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
A Journey of Infinite Enchantment in the Lesser Antillies
10 Days (9 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 December 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Dominica (+4 more), Saint Lucia, Grenada, Saint Vincent, Barbados
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,049
SUITE
$7,385
From 6,049
Cruise
Yachtsman's Caribbean Sea Jewels
22 Days (21 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 25 January 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+9 more), Saint Vincent, Grenada, Barbados, Curacao, Bonaire, Aruba, Colombia, Dominican Republic, Antigua and Barbuda
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$17,438
SUITE
$31,659
From 17,438
Cruise
A Journey From Miami To Miami
8 Days (7 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 14 February 2025
Countries Visited: USA, Mexico, Belize
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$5,029
SUITE
$6,138
From 5,029
Cruise
Bridgetown to Bridgetown
15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 22 December 2025
Countries Visited: Barbados, Saint Lucia, Grenada, Saint Martin (+5 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Dominica, Saint Vincent
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$14,553
BALCONY
$16,533
SUITE
$15,543
From 14,553
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
A Journey To Rum-soaked Isles And Castaway Bliss
8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 15 November 2024
Countries Visited: Barbados, Martinique, Saint Lucia, Antigua and Barbuda (+2 more), Puerto Rico, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,192
SUITE
$7,529
From 6,192
Cruise
Passage To Paradise
8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 13 December 2025
Countries Visited: USA, Belize, Honduras, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,488
SUITE
$7,557
Cruise
A Journey From Miami To Miami
10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 24 March 2025
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,168
SUITE
$7,519
From 6,168
Cruise
Classic Caribbean Yacht Harbors
8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Feb 2025
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+3 more), Virgin Islands, Saint Kitts and Nevis, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$6,149
SUITE
$11,282
From 6,149
Cruise
Idyllic West Indies
12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 09 March 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Barbados (+3 more), Grenada, Dominica, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,953
SUITE
$10,725
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