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Explore 415 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - November 2025
2 Sailors , 1 Cabin
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Showing 22 cruise vacations that match your search
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Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,032$1,368
per Cabin
4 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,032$1,368
per Cabin
Departing on:

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,714
per Cabin
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5 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,290$1,714
per Cabin
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Departing on:
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $600* off

Italy to France & Spain

  • Rome (Civitavecchia)
  • Cagliari, Sardinia, Italy
  • Tuscany/Cinque Terre (Marina di Carrara), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Valencia, Spain
  • Barcelona
Insider cabins from
$3,510$5,200
per Cabin
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9 nights
Scarlet Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$3,510$5,200
per Cabin
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Departing on:

True Crime Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,774
per Cabin
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5 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,290$1,774
per Cabin
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Departing on:

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,766$5,468
per Cabin
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7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$3,766$5,468
per Cabin
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Departing on:
UP TO $600 OFF

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,384$3,436
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,384$3,436
per Cabin
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Departing on:

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,704
per Cabin
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5 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,290$1,704
per Cabin
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Departing on:

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,390$1,926
per Cabin
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5 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,390$1,926
per Cabin
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Departing on:

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,672$2,348
per Cabin
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4 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,672$2,348
per Cabin
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Departing on:
UP TO $600 OFF

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,526$2,014
per Cabin
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7 nights
Scarlet Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,526$2,014
per Cabin
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Departing on:
UP TO $600 OFF

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,806$2,526
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,806$2,526
per Cabin
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Departing on:

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
$1,308$1,832
per Cabin
Loading
6 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,308$1,832
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
Insider cabins from
$2,800$4,146
per Cabin
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,800$4,146
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
$1,666$2,318
per Cabin
Loading
7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,666$2,318
per Cabin
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Departing on:
UP TO $600 OFF

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
Insider cabins from
$1,666$2,414
per Cabin
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,666$2,414
per Cabin
Loading
Departing on:

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,390$1,858
per Cabin
Loading
5 nights
Scarlet Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,390$1,858
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
$2,560$3,736
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,560$3,736
per Cabin
Loading
Departing on:
UP TO $600 OFF

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,310$3,300
per Cabin
Loading
7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,310$3,300
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
$1,666$2,400
per Cabin
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,666$2,400
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
Insider cabins from
$2,700$3,936
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,700$3,936
per Cabin
Loading
Departing on:

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
Insider cabins from
$1,860$2,730
per Cabin
Loading
6 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,860$2,730
per Cabin
Loading
Departing on:
UP TO $600 OFF

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,666$2,330
per Cabin
Loading
7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,666$2,330
per Cabin
Loading
Departing on: