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Explore 410 cruise vacations

Showing Loading cruise vacations: All Destinations, October 2025 - November 2025
1 Sailor , 1 Cabin
Ends Sep 30:
Rates from $109* pp/pn |
|
Caribbean Cruises
Showing 19 cruise vacations that match your search
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Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Insider cabins from
$2,550
per Cabin
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10 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$2,550
per Cabin
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Departing on:
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)$2,550

Fall Leaves to Miami Scenes

  • Québec City, Québec
  • Halifax, Nova Scotia
  • Saint John, New Brunswick
  • Eastport, Maine
  • Boston, Massachusetts
  • Charleston, South Carolina
  • Miami, Florida
Sea Terrace cabins from
$2,203$4,995
per Cabin
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13 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea Terrace cabins from
$2,203$4,995
per Cabin
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Departing on:
2025
Fri, Oct 03 - Thu, Oct 16
from (US$)$2,203Brilliant Lady's Inaugural Season
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $600* off
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Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$939$1,309
per Cabin
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5 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$939$1,309
per Cabin
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Departing on:
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)$939

Italy to France & Spain

  • Rome (Civitavecchia)
  • Cagliari, Sardinia, Italy
  • Tuscany/Cinque Terre (Marina di Carrara), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Valencia, Spain
  • Barcelona
Sea Terrace cabins from
$2,767$6,540
per Cabin
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9 nights
Scarlet Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea Terrace cabins from
$2,767$6,540
per Cabin
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Departing on:
2025
Tue, Oct 07 - Thu, Oct 16
from (US$)$2,767

True Crime Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,095$1,579
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$1,095$1,579
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,095

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Sea Terrace cabins from
$2,856$6,588
per Cabin
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7 nights
Resilient Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea Terrace cabins from
$2,856$6,588
per Cabin
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Departing on:
2025
Sun, Oct 12 - Sun, Oct 19
from (US$)$2,856

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
RockStar Quarters suites from
$9,719
per Cabin
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15 nights
Scarlet Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
RockStar Quarters suites from
$9,719
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$9,719
Only suites remaining
★
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
$2,169$3,221
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$2,169$3,221
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$)$2,169Brilliant Lady's Inaugural Season

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$930$1,290
per Cabin
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5 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$930$1,290
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)$930

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,093$1,575
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$1,093$1,575
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)$1,093

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
Sea Terrace cabins from
$3,469$5,259
per Cabin
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14 nights
Resilient Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea Terrace cabins from
$3,469$5,259
per Cabin
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Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)$3,469

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,306$1,897
per Cabin
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4 nights
Valiant Lady
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+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea View cabins from
$1,306$1,897
per Cabin
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)$1,306
★
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
$1,205
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$1,205
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)$1,205
★
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
$1,505
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ 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
$1,505
per Cabin
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Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$)$1,505Brilliant 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
Sea Terrace cabins from
$1,010$2,240
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea Terrace cabins from
$1,010$2,240
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)$1,010

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,492$2,189
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ 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
$1,492$2,189
per Cabin
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Departing on:
2025
Fri, Nov 07 - Wed, Nov 12
from (US$)$1,492
★
UP TO $600 OFF

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
$2,358
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ 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
$2,358
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$2,358Brilliant Lady's Inaugural Season
★
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
Sea Terrace cabins from
$2,195$5,184
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Sea Terrace cabins from
$2,195$5,184
per Cabin
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Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)$2,195

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,145$1,609
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ 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
$1,145$1,609
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)$1,145
Average starting price per cabin (incl. taxes & fees)