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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
(1)
Eastern Caribbean Voyage
8 Days (7 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departures: Nov 2025 to Nov 2025
Countries Visited: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+3 more), Sint Maarten, Virgin Islands, Puerto Rico
INSIDE
$1,909
OCEANVIEW
$2,514
BALCONY
$3,088
SUITE
$5,042
From 1,909
Cruise
(2)
Island Voyager
16 Days (15 Nights) New York to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 19 November 2024
Countries Visited: USA, Bermuda, Saint Barthelemy, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Grenada, Bonaire, Aruba
Cabin Upgrade Offer
INSIDE
$5,139
OCEANVIEW
$5,139
BALCONY
$6,208
SUITE
$8,722
From 5,139
Cruise
(9)
Caribbean
22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Oct 2025 to Jan 2026
Countries Visited: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+7 more), Barbados, Sint Maarten, Virgin Islands, Dominican Republic, Jamaica, Belize, Mexico
Exclusive Deal
INSIDE
$2,729
OCEANVIEW
$3,570
BALCONY
$4,511
SUITE
$12,381
From 2,729
Cruise
(2)
Remarkable Caribbean
18 Days (17 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 04 December 2024
Countries Visited: USA, Mexico, Belize, Honduras (+6 more), Antigua and Barbuda, Saint Lucia, Saint Barthelemy, Puerto Rico, Dominican Republic, Bahamas
Exclusive Deal
INSIDE
$5,491
OCEANVIEW
$6,105
BALCONY
$8,698
SUITE
$11,302
Cruise
(9)
Eastern Caribbean Celebration
13 Days (12 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 18 December 2025
Countries Visited: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+3 more), Barbados, Sint Maarten, Virgin Islands
Exclusive Deal
INSIDE
$2,528
OCEANVIEW
$3,320
BALCONY
$4,211
SUITE
$11,685
From 2,528
Cruise
(2)
Shimmering Strands
11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 11 December 2024
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Saint Barthelemy (+3 more), Puerto Rico, Dominican Republic, Bahamas
Cabin Upgrade Offer
INSIDE
$3,568
OCEANVIEW
$3,568
BALCONY
$5,251
SUITE
$5,855
From 3,568
Cruise
(2)
Caribbean Celebration
15 Days (14 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 20 December 2026
Countries Visited: USA, Dominican Republic, Virgin Islands, Dominica (+3 more), Barbados, Saint Lucia, Saint Kitts and Nevis
Exclusive Deal
INSIDE
$3,667
OCEANVIEW
$5,003
BALCONY
$5,152
SUITE
$11,884
From 3,667
Cruise
(1)
Southern Caribbean Voyage
8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departures: Nov 2025 to Dec 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
INSIDE
$1,909
OCEANVIEW
$2,514
BALCONY
$3,088
SUITE
$5,042
From 1,909
Cruise
(9)
Caribbean
22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Nov 2025 to Feb 2026
Countries Visited: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+7 more), Barbados, Sint Maarten, Virgin Islands, Turks and Caicos Islands, Jamaica, Belize, Mexico
Exclusive Deal
INSIDE
$2,729
OCEANVIEW
$3,521
BALCONY
$4,412
SUITE
$12,381
From 2,729
Cruise
(2)
Eastern Caribbean
13 Days (12 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 26 November 2025
Countries Visited: USA, Sint Maarten, Dominica, Barbados (+2 more), Saint Lucia, Saint Kitts and Nevis
Exclusive Deal
INSIDE
$2,181
OCEANVIEW
$3,221
BALCONY
$3,419
SUITE
$7,923
From 2,181
Cruise
(1)
Eastern Caribbean Voyage
14 Days (13 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Sint Maarten
INSIDE
$3,225
OCEANVIEW
$4,175
BALCONY
$5,095
SUITE
$8,428
From 3,225
Cruise
(1)
Eastern Caribbean Voyage
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Departures: Nov 2025 to Dec 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Sint Maarten
INSIDE
$3,474
OCEANVIEW
$4,539
BALCONY
$5,574
SUITE
$7,885
From 3,474
Cruise
(2)
Windward Island Escape
8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 22 January 2025
Countries Visited: Barbados, Martinique, Saint Barthelemy, Dominica (+3 more), Saint Lucia, Saint Vincent, Grenada
Exclusive Deal
INSIDE
$4,236
OCEANVIEW
$4,533
BALCONY
$5,454
SUITE
$7,127
New ReleaseCruise
(1)
Discover the Grenadines & Windwards islands
14 Days (13 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 27 December 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+4 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,405
BALCONY
-
SUITE
$11,123
Cruise
(9)
Western Caribbean
10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Oct 2025 to Jan 2026
Exclusive Deal
INSIDE
$1,388
OCEANVIEW
$1,834
BALCONY
$2,279
SUITE
$6,635
From 1,388
New ReleaseCruise
(1)
Discover the Best of the Caribbean
17 Days (16 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 20 November 2026
Countries Visited: Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda (+5 more), Guadeloupe, Martinique, Saint Lucia, Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
$11,276
BALCONY
-
SUITE
$15,078
Cruise
(9)
Caribbean
22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Dec 2025 to Mar 2026
Countries Visited: USA, Turks and Caicos Islands, Jamaica, Belize (+7 more), Mexico, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Exclusive Deal
INSIDE
$2,976
OCEANVIEW
$3,768
BALCONY
$4,610
SUITE
$13,173
From 2,976
Cruise
(9)
Caribbean
22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Oct 2025 to Jan 2026
Countries Visited: USA, Dominican Republic, Jamaica, Belize (+7 more), Mexico, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Exclusive Deal
INSIDE
$2,828
OCEANVIEW
$3,570
BALCONY
$4,412
SUITE
$12,381
From 2,828
Cruise
(1)
Eastern Caribbean Voyage
16 Days (15 Nights) Miami to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 31 October 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Sint Maarten (+8 more), Saint Barthelemy, Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
INSIDE
$3,726
OCEANVIEW
$4,791
BALCONY
$5,940
SUITE
$9,734
From 3,726
Cruise
(1)
Eastern Caribbean Voyage
15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 13 December 2025
Countries Visited: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+7 more), Sint Maarten, Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Vincent, Trinidad and Tobago
INSIDE
$3,477
OCEANVIEW
$4,542
BALCONY
$5,576
SUITE
$9,024
From 3,477
Cruise
(1)
Eastern Caribbean with St. Barths
8 Days (7 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara
Departures: Dec 2024 to Mar 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Martinique (+6 more), Guadeloupe, Antigua and Barbuda, Saint Barthelemy, Saint Martin, Anguilla, Saint Kitts and Nevis
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,539
BALCONY
-
SUITE
$6,450
Cruise
(1)
Eastern Caribbean Voyage
12 Days (11 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departures: Dec 2024 to Dec 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Sint Maarten (+2 more), Antigua and Barbuda, Saint Kitts and Nevis
Circle Club Voyage
INSIDE
$2,980
OCEANVIEW
$3,778
BALCONY
$4,568
SUITE
$5,990
From 2,980
Cruise
(9)
Caribbean
22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Nov 2025 to Mar 2026
Countries Visited: USA, Cayman Islands, Jamaica, Honduras (+7 more), Mexico, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Exclusive Deal
INSIDE
$2,531
OCEANVIEW
$3,521
BALCONY
$4,164
SUITE
$12,381
From 2,531
Cruise
(9)
Caribbean Celebration
22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 18 December 2025
Countries Visited: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+7 more), Barbados, Sint Maarten, Virgin Islands, Cayman Islands, Jamaica, Honduras, Mexico
Exclusive Deal
INSIDE
$4,065
OCEANVIEW
$4,907
BALCONY
$6,194
SUITE
$16,836
From 4,065
Cruise
Vibrant Hues Of Blue
15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 21 March 2025
Countries Visited: USA, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
$10,955
BALCONY
$13,757
SUITE
$15,242
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
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
Bridgetown to Bridgetown
8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departures: Dec 2025 to Mar 2026
Countries Visited: Barbados, Saint Vincent, Martinique, Saint Barthelemy (+3 more), Dominica, Grenada, Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$7,722
BALCONY
$8,910
SUITE
$8,118
From 7,722
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
$11,290
SUITE
$20,630
From 11,290
Cruise
Yachtsman's Caribbean
9 Days (8 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 (+4 more), Martinique, Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,056
SUITE
$9,853
From 5,056
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