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Departures
Duration
7 Days
86 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$1,300pp
$37,350pp
Countries
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358 Cruises (516 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
Philipsburg to Philipsburg
8 Days (7 Nights) Philipsburg to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departures: Jan 2026 to Feb 2026
Countries Visited: Saint Martin, Antigua and Barbuda, Virgin Islands, Montserrat (+3 more), Saint Lucia, Saint Vincent, Guadeloupe
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$7,573
BALCONY
$8,266
SUITE
$11,632
Cruise
Discover Eastern Caribbean & Grenadines
15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Departures: Dec 2024 to Nov 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+5 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,801
BALCONY
-
SUITE
$11,563
Cruise
Champagne, Confetti & The Caribbean
11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 28 December 2024
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,357
SUITE
$11,396
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
$5,395
BALCONY
$7,078
SUITE
-
Cruise
Cartagena to Philipsburg
17 Days (16 Nights) Cartagena to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 19 December 2025
Countries Visited: Colombia, Aruba, Curacao, Bonaire (+7 more), Saint Vincent, Barbados, Grenada, Martinique, Virgin Islands, Antigua and Barbuda, Saint Martin
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$11,484
BALCONY
$13,959
SUITE
$22,374
From 11,484
New ReleaseCruise
Discover the Hidden Treasures of the Caribbean
22 Days (21 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara
Departures: Dec 2024 to Jan 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+7 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Virgin Islands, Bonaire
Exclusive Deal
INSIDE
-
OCEANVIEW
$14,786
BALCONY
-
SUITE
$17,320
Cruise
Maya & Isle Mementos
11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 29 December 2025
Exclusive Deal
INSIDE
$4,964
OCEANVIEW
$5,499
BALCONY
$7,558
SUITE
$10,548
Cruise
Tropical Retreats
8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 19 February 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$4,407
SUITE
$7,070
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
$10,356
SUITE
$11,396
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
Hidden Caribbean Coves
11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 17 December 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Guadeloupe, Saint Lucia, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,467
SUITE
$11,140
Cruise
A Journey From Miami To Miami
11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2026
Countries Visited: USA, Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,613
SUITE
$9,296
From 7,613
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
$22,619
Cruise
A Journey From Miami To San Juan
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 20 December 2024
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$7,217
SUITE
$8,776
From 7,217
Cruise
Antillean Delights
16 Days (15 Nights) Oranjestad to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 27 November 2024
Countries Visited: Aruba, Curacao, Jamaica, Dominican Republic (+10 more), Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Guadeloupe, Martinique, Saint Lucia, Grenada, Barbados
Cabin Upgrade Offer
INSIDE
$4,828
OCEANVIEW
$4,828
BALCONY
$5,897
SUITE
$8,332
From 4,828
Cruise
Yachtsman's Island Jewels
15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 07 March 2026
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Guadeloupe, Dominica, Saint Lucia
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,942
SUITE
$15,665
From 9,942
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
Hidden Caribbean Coves
11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 27 November 2024
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Guadeloupe (+3 more), Saint Barthelemy, Puerto Rico, Dominican Republic
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,398
SUITE
-
Cruise
Gems Of The Lesser Antilles
11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 30 November 2024
Countries Visited: Barbados, Saint Vincent, Dominica, Saint Kitts and Nevis (+4 more), Aruba, Curacao, Bonaire, Trinidad and Tobago
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$7,077
SUITE
$12,294
From 7,077
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
Mutiple Deals Available
INSIDE
-
OCEANVIEW
-
BALCONY
$5,158
SUITE
$6,272
From 5,158
Cruise
Fort Lauderdale to New York
16 Days (15 Nights) Fort Lauderdale to New York
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 May 2025
Countries Visited: USA, Dominican Republic, Aruba, Saint Barthelemy (+2 more), Virgin Islands, Bermuda
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$11,434
BALCONY
$12,424
SUITE
$20,542
New ReleaseCruise
Discover the Pearls of the Caribbean
15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Departures: Dec 2024 to Dec 2026
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Bonaire, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,999
BALCONY
-
SUITE
$11,563
New ReleaseCruise
Quintessential Caribbean
8 Days (7 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Jan 2027 to Mar 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+2 more), Antigua and Barbuda, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,836
BALCONY
-
SUITE
$7,375
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
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
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
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
-
BALCONY
$8,613
SUITE
$20,097
From 8,613
Cruise
(2)
Transatlantic Crossing And Eastern Caribbean
29 Days (28 Nights) Hamburg to London
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 17 November 2025
Countries Visited: Germany, England, USA, Sint Maarten (+4 more), Dominica, Barbados, Saint Lucia, Saint Kitts and Nevis
Exclusive Deal
INSIDE
$4,810
OCEANVIEW
$6,790
BALCONY
$7,087
SUITE
$16,443
From 4,810
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