Explore 414 cruise vacations

Showing 0 cruise vacations: Caribbean, June 2025 - April 2027
UP TO $300 IN ONBOARD CREDIT
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On top of 70% off 2nd Sailor + balcony upgrades
Showing 269 cruise vacations that match your search
Showing 269 cruise vacations that match your search

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady, Resilient Lady & Scarlet Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027Best Rate
Mon, Jan 04 - Sat, Jan 09
from (US$)
2025
Sun, Jun 15 - Fri, Jun 20
from (US$)
2025
Sun, Sep 07 - Fri, Sep 12
from (US$)

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026Best Rate
Mon, Aug 31 - Sat, Sep 05
from (US$)
2025
Fri, Jun 20 - Wed, Jun 25
from (US$)
2025
Fri, Jul 04 - Wed, Jul 09
from (US$)

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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4 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026Best Rate
Thu, Sep 24 - Mon, Sep 28
from (US$)
2025
Wed, Jun 25 - Sun, Jun 29
from (US$)
2025
Wed, Jul 09 - Sun, Jul 13
from (US$)
* Port changes in place on select sailings — see full cruise details

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2026Best Rate
Sun, Jan 25 - Fri, Jan 30
from (US$)
2025
Sun, Jun 29 - Fri, Jul 04
from (US$)
2025
Sun, Jul 27 - Fri, Aug 01
from (US$)

Grand Cayman, Costa Maya & More

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

Grand Turk, Puerto Plata & More

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

Virgin Voyages Comedy Fest from Miami

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2025
Sun, Aug 10 - Fri, Aug 15
from (US$)

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
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15 nights
Scarlet Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)
RED HOT

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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
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per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$) Brilliant Lady's Inaugural Season

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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4 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 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$)

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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
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per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 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$)

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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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

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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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:
2027Best Rate
Sat, Jan 02 - Sat, Jan 09
from (US$)
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)
2026
Sat, Mar 21 - Sat, Mar 28
from (US$)

Western Caribbean Charm

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

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Sat, Jan 16 - Sat, Jan 23
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)

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
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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:
2025Best Rate
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season
2026
Thu, Feb 12 - Fri, Feb 20
from (US$) Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2026Best Rate
Sat, Sep 19 - Thu, Sep 24
from (US$)
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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:
2026Best Rate
Sat, Jan 24 - Sat, Jan 31
from (US$)
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)

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
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 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$)

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
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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
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Departing on:
2026Best Rate
Fri, Feb 20 - Sun, Mar 01
from (US$) Brilliant Lady's Inaugural Season
2025
Fri, Nov 28 - Sun, Dec 07
from (US$) 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
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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$)

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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:
2026Best Rate
Sat, Jan 17 - Sat, Jan 24
from (US$)
2025
Sat, Nov 29 - Sat, Dec 06
from (US$)

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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per Cabin
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8 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
Fri, Dec 05 - Sat, Dec 13
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season
2026
Sun, Mar 01 - Thu, Mar 12
from (US$) Brilliant Lady's Inaugural Season

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$)

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
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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, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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, Dec 20 - Sat, Dec 27
from (US$)
2026
Sun, Dec 20 - Sun, Dec 27
from (US$)

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
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$)

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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4 nights
Scarlet 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
Wed, Dec 24 - Sun, Dec 28
from (US$)
2026
Mon, Dec 21 - Sat, Dec 26
from (US$)
* Port changes in place on select sailings — see full cruise details

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
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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
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Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$) Brilliant Lady's Inaugural Season

Resilient New Year's Ahoy!

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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:
2026Best Rate
Sun, Dec 27 - Sun, Jan 03
from (US$)
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

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
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 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$)

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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per Cabin
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Departing on:
2025Best Rate
Sun, Dec 28 - Fri, Jan 02
from (US$)
2026
Wed, Dec 30 - Mon, Jan 04
from (US$)
* Port changes in place on select sailings — see full cruise details

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 03 - Sat, Jan 10
from (US$)
2027
Sat, Feb 06 - Sat, Feb 13
from (US$)

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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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:
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
+ free balcony upgrade
SWING INTO SUMMER: 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

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Resilient Lady & 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:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)
2026
Sun, Nov 01 - Sun, Nov 08
from (US$)

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
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)

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
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per Cabin
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7 nights
Valiant Lady
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Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
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6 nights
Brilliant Lady
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)

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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7 nights
Valiant Lady
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Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)

Magnetic Miami to Gorgeous George Town

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$) Brilliant Lady's Inaugural Season

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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7 nights
Valiant Lady
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)

Aruba, Curaçao and the St. Isles

  • 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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7 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)

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
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7 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)

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
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7 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)

Red Hot Sailing Club Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$) Brilliant Lady's Inaugural Season

Costa Mayan Caves & Honduran Waves

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
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6 nights
Resilient Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
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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7 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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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$)
RED HOT

Puerto Rican Nights & St. Croix Delights

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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8 nights
Resilient Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)

Puerto Plata, San Juan & Tortola

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Miami, Florida
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7 nights
Scarlet Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from (US$)

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Resilient Lady & Scarlet Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026Best Rate
Mon, Nov 09 - Sat, Nov 14
from (US$)
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)

Miami to Grand Turk: Halloween Edition

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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6 nights
Scarlet Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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6 nights
Resilient Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (US$)

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Scarlet Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
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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7 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)

November Nights in the Eastern Caribbean

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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8 nights
Resilient Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (US$)

Caribbean East: Virgin & Saint Isles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • San Juan, Puerto Rico
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6 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027Best Rate
Sat, Jan 23 - Fri, Jan 29
from (US$)
2026
Sat, Nov 14 - Fri, Nov 20
from (US$)
2027
Sat, Mar 13 - Fri, Mar 19
from (US$)

St. Isles & Sun-soaked Seas

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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10 nights
Brilliant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026Best Rate
Sun, Nov 15 - Wed, Nov 25
from (US$)
2027
Mon, Jan 25 - Thu, Feb 04
from (US$)
2027
Mon, Feb 22 - Thu, Mar 04
from (US$)

Captivating Costa Maya & Cozumel Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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6 nights
Resilient Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Mon, Nov 16 - Sun, Nov 22
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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8 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (US$)

Jamaican Waves & Bimini Breeze

  • Miami, Florida
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Scarlet Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027Best Rate
Mon, Feb 15 - Sat, Feb 20
from (US$)
2026
Mon, Nov 23 - Sat, Nov 28
from (US$)

Antiguan Elegance & Sunny St. Isles

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Nov 28 - Sat, Dec 05
from (US$)

St. Maarten, Tortola, San Juan & more

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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10 nights
Brilliant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (US$)
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)
2027
Mon, Mar 08 - Thu, Mar 18
from (US$)

Pre-Holiday Caribbean Getaway

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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9 nights
Brilliant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Mon, Dec 14 - Wed, Dec 23
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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7 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Dec 19 - Sat, Dec 26
from (US$)

Brilliant Caribbean Holidays

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Miami, Florida
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5 nights
Brilliant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Wed, Dec 23 - Mon, Dec 28
from (US$)

Valiant New Year's Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Fort-de-France, Martinique
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Sat, Dec 26 - Sat, Jan 02
from (US$)

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Tortola, British Virgin Islands
  • St. John's, Antigua
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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10 nights
Brilliant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2026
Mon, Dec 28 - Thu, Jan 07
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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8 nights
Valiant Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Fri, Jan 29 - Sat, Feb 06
from (US$)

San Juan & St. Isles: Valentine’s Voyage

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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10 nights
Brilliant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Mon, Feb 08 - Thu, Feb 18
from (US$)

Key West & Bimini: Valentine’s Voyage

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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4 nights
Scarlet Lady
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SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
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
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7 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Sat, Feb 13 - Sat, Feb 20
from (US$)

PR, DR & Bimini: Valentine’s Voyage

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Sun, Feb 14 - Sun, Feb 21
from (US$)

Saint Isles & The Greater Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Sat, Feb 20 - Sat, Feb 27
from (US$)

Barbados, Dominica & St. Isle Spring

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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8 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Fri, Mar 19 - Sat, Mar 27
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
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7 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Sat, Mar 27 - Sat, Apr 03
from (US$)

San Juan to Miami: Dominican Daze

  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady
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+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
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Departing on:
2027
Sat, Apr 10 - Thu, Apr 15
from (US$)
Average starting price per cabin (incl. taxes & fees)