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Explore 406 cruise vacations

Showing Loading cruise vacations: All Destinations, June 2025 - December 2025
6-8 & 9-12 nights
Departs Miami, Florida & San Juan, Puerto Rico
UP TO $300 IN ONBOARD CREDIT
On Caribbean sailings 7 nights or longer
|
On top of 70% off 2nd Sailor + balcony upgrades

70% off 2nd Sailor + Free balcony upgrade ends in…

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Showing 28 cruise vacations that match your search
Showing 28 cruise vacations that match your search
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DEAL

Grand Cayman, Costa Maya & More

  • Miami, Florida
  • George Town, Grand Cayman
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
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Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from (US$)
DEAL

Grand Turk, Puerto Plata & More

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sun, Jul 20 - Sun, Jul 27
from (US$)
DEAL

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$) Brilliant Lady's Inaugural Season
DEAL

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)
DEAL

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$) Brilliant Lady's Inaugural Season

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
Insider cabins from
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)
DEAL

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$) Brilliant Lady's Inaugural Season
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
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)
DEAL

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
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
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
DEAL

Sunny San Juan & Isles of Beach Miles

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season
DEAL

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)
2025
Sat, Dec 13 - Sat, Dec 20
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
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
DEAL

Antigua Waves & Grand Turk Caves

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Sea View cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$) Brilliant Lady's Inaugural Season

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
Sea View cabins from
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)
DEAL

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
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
Sea View cabins from
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
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
Insider cabins from
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season
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
+ free balcony upgrade
SWING INTO SUMMER: 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

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
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
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)
DEAL

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)
Average starting price per cabin (incl. taxes & fees)