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Explore 399 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - October 2026
Departs San Juan, Puerto Rico
Showing 21 cruise vacations that match your search
Showing 21 cruise vacations that match your search
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DEAL

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026Best Rate
Sat, Mar 21 - Sat, Mar 28
from (US$)
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)
DEAL

Sunny Miles of Tropical Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026Best Rate
Sat, Feb 28 - Sat, Mar 07
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
DEAL

Thanksgiving in the Lesser Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)

San Juan to Barbados & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Roseau, Dominica
  • Bridgetown, Barbados
  • San Juan, Puerto Rico
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6 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)
DEAL

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

St. Lucia, St. Maarten, Barbados & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Roseau, Dominica
  • Bridgetown, Barbados
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)
DEAL

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)
DEAL

Valiant New Year’s Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)
DEAL

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
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)
DEAL

Virgin Island Views & Saint Isle Blues

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Basseterre, St. Kitts and Nevis
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)
DEAL

St. Kitts, Barbados, Martinique & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • 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
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
DEAL

Barbados, Antigua, BVI & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)
DEAL

Antigua & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)
DEAL

St. Lucia, Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)

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
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)
DEAL

Antigua, Martinique, & Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • 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:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)
DEAL

Quaint Castries to Elegant Antigua

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • 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:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)
DEAL

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
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:
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)
DEAL

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
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:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)
Average starting price per cabin (incl. taxes & fees)