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Departures
Duration
7 Days
86 Days
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Ship Size
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Price
$1,600pp
$37,350pp
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362 Cruises (519 Cruise Departures)
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
A Blissful Escape
15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 28 February 2026
Countries Visited: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Guadeloupe, Martinique, Saint Kitts and Nevis, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$13,608
SUITE
$14,865
Cruise
Panama City to Fort Lauderdale
8 Days (7 Nights) Panama City to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 20 May 2025
Countries Visited: Panama, Colombia, USA
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
$4,158
BALCONY
$5,049
SUITE
-
From 4,158
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
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
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
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
An Extended Journey Of Caribbean Melodies And ABC Islands
15 Days (14 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2025
Countries Visited: USA, Virgin Islands, Dominica, Guadeloupe (+7 more), Saint Martin, Puerto Rico, Aruba, Curacao, Bonaire, Trinidad and Tobago, Barbados
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$9,702
SUITE
$11,880
From 9,702
Cruise
Yucatan & Leeward Seafarer
25 Days (24 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 04 January 2026
Countries Visited: USA, Mexico, Belize, Guatemala (+8 more), Honduras, Jamaica, Cayman Islands, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,463
SUITE
$23,235
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
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
Elegant Tropical Enclaves
24 Days (23 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 08 April 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Grenada (+5 more), Barbados, Dominica, Saint Barthelemy, Bahamas, Bermuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$13,040
SUITE
$21,188
Cruise
Bridgetown to Philipsburg
8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 28 December 2025
Countries Visited: Barbados, Saint Vincent, Grenada, Martinique (+3 more), Virgin Islands, Antigua and Barbuda, Saint Martin
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,603
BALCONY
$10,395
SUITE
$12,771
From 9,603
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
An Extended Journey Of Caribbean Rhythms
15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 22 November 2024
Countries Visited: USA, Dominica, Guadeloupe, Saint Martin (+5 more), Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$11,682
SUITE
$14,256
From 11,682
Cruise
A Journey From Miami To Miami
11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 25 January 2026
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,168
SUITE
$8,752
From 7,168
Cruise
A Grand Journey From The Mississippi Delta To Mayan Kingdoms
32 Days (31 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 January 2025
Countries Visited: USA, Mexico, Bahamas, Saint Barthelemy (+9 more), Guadeloupe, Saint Vincent, Martinique, Antigua and Barbuda, Virgin Islands, Cayman Islands, Costa Rica, Panama, Colombia
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$21,829
SUITE
$26,730
From 21,829
Cruise
A Journey From Miami To Miami
11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 January 2026
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,168
SUITE
$8,752
From 7,168
Cruise
Caribbean Twilight
20 Days (19 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 20 March 2025
Countries Visited: USA, Mexico, Belize, Honduras (+8 more), Aruba, Curacao, Bonaire, Grenada, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$11,975
SUITE
$16,886
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
$4,110
SUITE
$5,714
From 3,427
Cruise
Southern Caribbean Holiday & Aruba, Bonaire & Curacao
13 Days (12 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 22 December 2025
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Saint Kitts and Nevis (+6 more), Montserrat, Curacao, Aruba, Bonaire, Grenada, Saint Vincent
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$8,846
SUITE
$17,009
From 8,846
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
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
Western Caribbean Escape
8 Days (7 Nights) Tampa to Tampa
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 18 March 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
$3,644
OCEANVIEW
$4,020
BALCONY
$5,169
SUITE
$6,604
Cruise
Fort Lauderdale to Fort Lauderdale
15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Ray
Departure: 23 December 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Bonaire (+3 more), Curacao, Saint Kitts and Nevis, Turks and Caicos Islands
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$15,048
From 15,048
Cruise
Exotic Caribbean Isles
15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Feb 2026
Countries Visited: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Virgin Islands, Sint Maarten, Martinique, Saint Vincent, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,858
SUITE
$15,665
From 9,858
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
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
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
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
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