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Explore 400 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - May 2026
2 Sailors , 1 Cabin
Showing 13 cruise vacations that match your search
Showing 13 cruise vacations that match your search
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DEAL

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Scarlet Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)

One-way to SJ: DR, St. Maarten & BVI

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
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per Cabin
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6 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
Sun, Nov 02 - Sat, Nov 08
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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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, Feb 28 - Sat, Mar 07
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
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
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
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
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:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
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
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
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
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, 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
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, 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
BOOK NOW
+ 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, 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$)
Average starting price per cabin (incl. taxes & fees)