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Departures
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$1,300pp
$74,780pp
Countries
Filter Results
359 Cruises (518 Cruise Departures)
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
A Journey From Miami To San Juan
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 14 January 2025
Countries Visited: USA, Virgin Islands, Saint Barthelemy, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,401
SUITE
$5,371
From 4,401
Cruise
Bridgetown to Cartagena
10 Days (9 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 05 March 2026
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,603
BALCONY
$10,296
SUITE
$15,048
From 9,603
Cruise
Discover Eastern Caribbean & Grenadines
15 Days (14 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Departures: Mar 2025 to Mar 2027
Countries Visited: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
$9,049
BALCONY
-
SUITE
$11,563
Cruise
A Journey From Miami To Miami
10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 January 2025
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,856
SUITE
$8,370
From 6,856
Cruise
Fort Lauderdale to Bridgetown
12 Days (11 Nights) Fort Lauderdale to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 16 January 2025
Countries Visited: USA, Puerto Rico, Saint Barthelemy, Saint Kitts and Nevis (+6 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Grenada, Saint Vincent, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,702
BALCONY
$11,187
SUITE
$17,127
From 9,702
Cruise
Antillean Delights
16 Days (15 Nights) Oranjestad to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 27 November 2024
Countries Visited: Aruba, Curacao, Jamaica, Dominican Republic (+10 more), Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Guadeloupe, Martinique, Saint Lucia, Grenada, Barbados
Cabin Upgrade Offer
INSIDE
$4,828
OCEANVIEW
$4,828
BALCONY
$5,897
SUITE
$8,332
From 4,828
Cruise
Grenadines & Windwards yachting
8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Departures: Mar 2025 to Mar 2027
Countries Visited: Barbados, Grenada, Saint Vincent
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,341
BALCONY
-
SUITE
$6,747
Cruise
Yachtsman's Caribbean
8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Mar 2026
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+3 more), Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,476
SUITE
$8,673
From 5,476
Cruise
Tropical Harmony
10 Days (9 Nights) Bridgetown to Tampa
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 22 February 2026
Exclusive Deal
INSIDE
$4,189
OCEANVIEW
$4,882
BALCONY
$6,485
SUITE
$8,396
Cruise
Bridgetown to Bridgetown
12 Days (11 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 27 January 2025
Countries Visited: Barbados, Saint Vincent, Curacao, Aruba (+5 more), Bonaire, Trinidad and Tobago, Grenada, Martinique, Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$10,989
BALCONY
$12,375
SUITE
$18,612
From 10,989
Cruise
Auburn Sunsets, Turquoise Seas
16 Days (15 Nights) New York to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 02 November 2025
Countries Visited: USA, Bermuda, Saint Barthelemy, Saint Lucia (+5 more), Barbados, Grenada, Curacao, Bonaire, Aruba
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$16,124
SUITE
$18,045
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
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
Bridgetown to Fort Lauderdale
12 Days (11 Nights) Bridgetown to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Moon
Departure: 21 March 2025
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Martinique (+6 more), Antigua and Barbuda, Saint Barthelemy, Sint Maarten, Puerto Rico, Turks and Caicos Islands, USA
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,702
BALCONY
$10,989
SUITE
$16,731
From 9,702
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
Cruise
A Journey From Miami To Miami
11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2026
Countries Visited: USA, Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,613
SUITE
$9,296
From 7,613
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
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
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
$7,690
Cruise
Fort Lauderdale to New York
16 Days (15 Nights) Fort Lauderdale to New York
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 May 2025
Countries Visited: USA, Dominican Republic, Aruba, Saint Barthelemy (+2 more), Virgin Islands, Bermuda
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$12,672
BALCONY
$13,167
SUITE
$20,493
From 12,672
Cruise
Lesser Antilles In Depth
22 Days (21 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 30 November 2024
Countries Visited: Barbados, Saint Vincent, Dominica, Saint Kitts and Nevis (+11 more), Aruba, Bonaire, Curacao, Trinidad and Tobago, Saint Lucia, Antigua and Barbuda, Saint Martin, Virgin Islands, Guadeloupe, Martinique, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$12,726
SUITE
$23,160
From 12,726
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
$6,233
SUITE
$11,282
From 6,233
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
Sunlit Seascapes
11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 09 February 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis (+3 more), Guadeloupe, Saint Lucia, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,784
SUITE
-
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
$5,504
SUITE
$6,692
From 5,504
Cruise
Philipsburg to Philipsburg
8 Days (7 Nights) Philipsburg to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departures: Jan 2026 to Feb 2026
Countries Visited: Saint Martin, Antigua and Barbuda, Virgin Islands, Montserrat (+3 more), Saint Lucia, Saint Vincent, Guadeloupe
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,910
BALCONY
$9,504
SUITE
$12,078
From 8,910
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 Jan 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+7 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Virgin Islands, Bonaire
Exclusive Deal
INSIDE
-
OCEANVIEW
$13,548
BALCONY
-
SUITE
$17,320
Cruise
Discover Eastern Caribbean & Grenadines
15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Departures: Dec 2024 to Nov 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+5 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,801
BALCONY
-
SUITE
$11,563
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
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