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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
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
Idyllic West Indies
12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 08 April 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Grenada (+3 more), Barbados, Dominica, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,972
SUITE
$10,734
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
$12,554
SUITE
-
From 12,554
Cruise
Yachtsman's Caribbean
8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Mar 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+3 more), Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$6,233
SUITE
$11,366
From 6,233
Cruise
A Caribbean Holiday
11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 18 December 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,060
SUITE
$11,099
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
Caribbean Chorus
11 Days (10 Nights) Bridgetown to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 12 December 2024
Countries Visited: Barbados, Grenada, Saint Vincent, Saint Lucia (+6 more), Dominica, Antigua and Barbuda, Saint Barthelemy, Puerto Rico, Dominican Republic, USA
Cabin Upgrade Offer
INSIDE
$3,427
OCEANVIEW
$3,427
BALCONY
$4,189
SUITE
$6,872
From 3,427
Cruise
Gems Of The Caribbean
15 Days (14 Nights) Philipsburg to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Feb 2026
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Saint Lucia, Montserrat, Antigua and Barbuda
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,858
SUITE
$15,665
From 9,858
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
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, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+2 more), Antigua and Barbuda, Guadeloupe
Exclusive Savings
INSIDE
-
OCEANVIEW
$10,526
BALCONY
$14,162
SUITE
$15,200
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
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
Cruise
Bridgetown to Cartagena
10 Days (9 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 10 December 2025
Countries Visited: Barbados, Saint Lucia, Saint Vincent, Curacao (+3 more), Bonaire, Aruba, Colombia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,009
BALCONY
$9,504
SUITE
$14,058
From 9,009
Cruise
Fort Lauderdale to Bridgetown
13 Days (12 Nights) Fort Lauderdale to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 10 November 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Barthelemy (+6 more), Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Saint Lucia, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$10,494
BALCONY
$11,979
SUITE
$18,909
From 10,494
Cruise
Colorful Caribbean Shores
15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 05 March 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+6 more), Grenada, Saint Vincent, Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,132
SUITE
$15,310
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
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
$10,359
SUITE
$11,399
Cruise
Tropical Connoisseur
13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 05 December 2024
Countries Visited: USA, Mexico, Guatemala, Belize (+4 more), Honduras, Cayman Islands, Jamaica, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,996
SUITE
$9,550
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
Bridgetown to Bridgetown
9 Days (8 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 13 March 2025
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$5,049
BALCONY
$6,930
SUITE
$11,781
From 5,049
Cruise
Caribbean Gems In Depth
15 Days (14 Nights) Philipsburg to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Feb 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$11,879
SUITE
$20,462
From 11,879
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
Island Odyssey: Bahamas to the Grenadines
13 Days (12 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse I
Departure: 24 October 2024
Countries Visited: Bahamas, Puerto Rico, Virgin Islands, Saint Barthelemy (+5 more), Montserrat, Antigua and Barbuda, Guadeloupe, Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$11,232
SUITE
$30,725
Cruise
Willemstad to Bridgetown
10 Days (9 Nights) Willemstad to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 12 December 2024
Countries Visited: Curacao, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+5 more), Guadeloupe, Saint Lucia, Trinidad and Tobago, Saint Vincent, Barbados
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
$6,732
BALCONY
$8,712
SUITE
$13,860
From 6,732
New ReleaseCruise
Discover the Vibes of the Caribbean
14 Days (13 Nights) Miami to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands, Puerto Rico (+4 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,712
BALCONY
-
SUITE
$10,430
Cruise
Sand, Surf & Rum
11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 January 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
$11,396
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
Season Of Sunshine
8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 06 December 2024
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,483
BALCONY
$6,958
SUITE
$6,958
Cruise
Lush Islands, Lovely Shores
8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 03 January 2026
Countries Visited: USA, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,634
SUITE
$7,693
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