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Departures
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$1,600pp
$37,350pp
Countries
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369 Cruises (529 Cruise Departures)
Cruise
(1)
Eastern Caribbean Voyage
19 Days (18 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Sint Maarten, USA
INSIDE
$4,478
OCEANVIEW
$5,888
BALCONY
$7,153
SUITE
$11,751
From 4,478
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
$7,048
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
New ReleaseCruise
(1)
Classic Caribbean
10 Days (9 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
$7,915
BALCONY
-
SUITE
$10,177
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
INSIDE
$3,075
OCEANVIEW
$4,164
BALCONY
$4,956
SUITE
$12,381
From 3,075
Cruise
(1)
Eastern Caribbean Voyage
9 Days (8 Nights) Miami to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 31 October 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Sint Maarten (+2 more), Saint Barthelemy, Puerto Rico
INSIDE
$2,161
OCEANVIEW
$2,881
BALCONY
$3,571
SUITE
$5,755
From 2,161
Cruise
(1)
Southern Caribbean Voyage
9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+3 more), Saint Vincent, Trinidad and Tobago, Barbados
INSIDE
$2,161
OCEANVIEW
$2,881
BALCONY
$3,571
SUITE
$5,755
From 2,161
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
$4,251
SUITE
$5,855
From 3,568
Cruise
(2)
Caribbean Celebration
13 Days (12 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 22 December 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Sint Maarten
INSIDE
$3,132
OCEANVIEW
$4,429
BALCONY
$4,617
SUITE
$9,705
From 3,132
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
(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
INSIDE
$4,758
OCEANVIEW
$5,748
BALCONY
$7,233
SUITE
$16,836
From 4,758
Cruise
(1)
Caribbean Quest Voyage
12 Days (11 Nights) Panama City to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 15 March 2026
INSIDE
$3,963
OCEANVIEW
$4,912
BALCONY
$5,832
SUITE
$6,752
From 3,963
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)
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
INSIDE
$2,973
OCEANVIEW
$3,864
BALCONY
$4,854
SUITE
$11,685
From 2,973
Cruise
(9)
Western Caribbean
10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Nov 2025 to Mar 2026
INSIDE
$1,636
OCEANVIEW
$1,982
BALCONY
$2,576
SUITE
$6,239
From 1,636
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
(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
INSIDE
$4,261
OCEANVIEW
$5,746
BALCONY
$5,944
SUITE
$11,884
From 4,261
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
-
OCEANVIEW
$6,105
BALCONY
$8,392
SUITE
$11,302
New ReleaseCruise
(1)
Caribbean Sojourn
7 Days (6 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 03 January 2027
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+3 more), Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Exclusive Deal
INSIDE
-
OCEANVIEW
$4,648
BALCONY
-
SUITE
$5,826
Cruise
(2)
Calypso Sands
13 Days (12 Nights) Cartagena to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 11 March 2025
Countries Visited: Colombia, Aruba, Curacao, Trinidad and Tobago (+5 more), Saint Vincent, Guadeloupe, Antigua and Barbuda, Puerto Rico, USA
Exclusive Deal
INSIDE
$6,082
OCEANVIEW
$6,765
BALCONY
$8,824
SUITE
$11,230
Cruise
(1)
Eastern Caribbean Voyage
15 Days (14 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 25 November 2024
Countries Visited: USA, Dominican Republic, Virgin Islands, Sint Maarten (+5 more), Saint Kitts and Nevis, Dominica, Barbados, Saint Lucia, Antigua and Barbuda
Circle Club Voyage
INSIDE
$3,932
OCEANVIEW
$3,723
BALCONY
$5,534
SUITE
$9,155
From 3,723
Cruise
(1)
Eastern Caribbean Voyage
13 Days (12 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 30 November 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Sint Maarten (+2 more), Antigua and Barbuda, Saint Kitts and Nevis
INSIDE
$3,150
OCEANVIEW
$4,216
BALCONY
$5,250
SUITE
$6,744
From 3,150
Cruise
(2)
Steel Drum Serenade
11 Days (10 Nights) Bridgetown to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 29 January 2025
Countries Visited: Barbados, Saint Vincent, Grenada, Curacao (+4 more), Aruba, Jamaica, Bahamas, USA
Exclusive Deal
INSIDE
$5,258
OCEANVIEW
$5,635
BALCONY
$7,090
SUITE
$8,862
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
INSIDE
$3,273
OCEANVIEW
$4,263
BALCONY
$5,352
SUITE
$12,381
From 3,273
Cruise
(2)
Caribbean Collage
23 Days (22 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 01 March 2025
Countries Visited: USA, Mexico, Belize, Honduras (+10 more), Costa Rica, Panama, Colombia, Aruba, Curacao, Trinidad and Tobago, Saint Vincent, Guadeloupe, Antigua and Barbuda, Puerto Rico
Exclusive Deal
INSIDE
$9,487
OCEANVIEW
$10,715
BALCONY
$14,220
SUITE
$18,091
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
$7,237
SUITE
$8,370
From 7,237
Cruise
Fort Lauderdale to Bridgetown
9 Days (8 Nights) Fort Lauderdale to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 05 March 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Martinique, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$4,851
BALCONY
$6,633
SUITE
$11,484
From 4,851
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
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 (+6 more), Virgin Islands, USA, Anguilla, Dominica, Martinique, Barbados
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$11,682
SUITE
$14,256
From 11,682
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