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Explore 419 cruise vacations

Showing Loading cruise vacations: Caribbean, August 2025 - November 2027
Showing 20 cruise vacations that match your search
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★DEAL

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$) Brilliant Lady's Inaugural Season

Nicky Jam x Virgin Voyages

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Roseau, Dominica
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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8 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)
★DEAL

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sun, Mar 01 - Thu, Mar 12
from (US$) Brilliant Lady's Inaugural Season
2025
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Sat, Feb 06 - Sat, Feb 13
from (US$)
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$) Brilliant Lady's Inaugural Season

Magnetic Miami to Gorgeous George Town

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$) Brilliant Lady's Inaugural Season

Valiant Valentine's Voyage

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)

Sunsets in the Lesser Antilles

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Dec 05 - Sat, Dec 12
from (US$)
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)
2027
Sat, Jan 09 - Sat, Jan 16
from (US$)

Valiant's Haunted Halloween Soirée

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)

Thanksgiving: St. Isles, Aruba & Curaçao

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Basseterre, St. Kitts and Nevis
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (US$)

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Fort-de-France, Martinique
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Dec 19 - Sat, Dec 26
from (US$)

Puerto Rico to Aruba, Bonaire & More

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Kralendijk, Bonaire
  • Fort-de-France, Martinique
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2027
Fri, Jan 29 - Sat, Feb 06
from (US$)

Lesser Antilles: Valentine's Day

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2027
Sat, Feb 13 - Sat, Feb 20
from (US$)

Colorful Curaçao, Aruba & Antigua

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2027
Sat, Mar 27 - Sat, Apr 03
from (US$)
Average starting price per cabin (incl. taxes & fees)