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Departures
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$1,300pp
$74,780pp
Countries
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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 Mar 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
$6,906
SUITE
$11,366
From 6,906
Cruise
Maya To Island Heritage
13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 04 January 2026
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,628
SUITE
$12,172
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 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
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
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
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
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
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
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
$9,936
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
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
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
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
$9,842
SUITE
$10,436
Cruise
Festive Caribbean
15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 22 December 2024
Countries Visited: USA, Jamaica, Aruba, Curacao (+6 more), Saint Vincent, Barbados, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Deal
INSIDE
$6,611
OCEANVIEW
$7,225
BALCONY
$9,670
SUITE
$13,917
Cruise
Iconic Islands To Empire City
17 Days (16 Nights) Miami to New York
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 24 June 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Saint Lucia, Saint Barthelemy, Puerto Rico, Bermuda
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,206
SUITE
$15,978
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
$14,713
SUITE
$21,188
Cruise
Exotic Caribbean In Depth
15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Mar 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
$12,468
SUITE
$20,462
From 12,468
Cruise
A Journey From Miami To Miami
8 Days (7 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 November 2025
Countries Visited: USA, Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,712
SUITE
$5,752
From 4,712
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
A Journey From San Juan To Miami
10 Days (9 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Dominican Republic, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$9,935
SUITE
$12,118
From 9,935
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
New York to Willemstad
10 Days (9 Nights) New York to Willemstad
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 28 October 2024
Countries Visited: USA, Bermuda, Saint Barthelemy, Curacao
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
$6,831
BALCONY
$8,613
SUITE
$19,305
From 6,831
New ReleaseCruise
Caribbean escapade
8 Days (7 Nights) Miami to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands, Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,440
BALCONY
-
SUITE
$6,979
Cruise
Island Inspiration
17 Days (16 Nights) Boston to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 27 October 2025
Countries Visited: USA, Bermuda, Saint Barthelemy, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Grenada, Bonaire, Aruba
Exclusive Deal
INSIDE
$5,406
OCEANVIEW
$5,941
BALCONY
$8,238
SUITE
$11,287
New ReleaseCruise
Caribbean Escapade
8 Days (7 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 21 November 2026
Countries Visited: Puerto Rico, Turks and Caicos Islands, Bahamas, USA
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,440
BALCONY
-
SUITE
$6,979
Cruise
(2)
Transatlantic Crossing And Caribbean Celebration
21 Days (20 Nights) New York to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 22 December 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+2 more), Sint Maarten, England
Exclusive Deal
INSIDE
$4,461
OCEANVIEW
$6,392
BALCONY
$6,540
SUITE
$17,430
From 4,461
Cruise
(2)
Transatlantic Crossing And Caribbean Celebration
23 Days (22 Nights) New York to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 20 December 2026
Countries Visited: USA, Dominican Republic, Virgin Islands, Dominica (+4 more), Barbados, Saint Lucia, Saint Kitts and Nevis, England
Exclusive Deal
INSIDE
$5,105
OCEANVIEW
$6,887
BALCONY
$7,085
SUITE
$16,441
From 5,105
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