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Explore 414 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - October 2025
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Extra savings on 7+ night Caribbean winter cruises.
Showing 15 cruise vacations that match your search
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Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
RockStar Quarters suites from
$6,250
per Cabin
5 nights
Valiant Lady
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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
$6,250
per Cabin
Departing on:
2025
Sun, Sep 21 - Fri, Sep 26
from (US$)$6,250
Only suites remaining

Autumn Leaves: New York to Quebec

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • Québec City, Québec
Mega RockStar Quarters suites from
$15,580
per Cabin
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Mega RockStar Quarters suites from
$15,580
per Cabin
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Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (US$)$15,580Brilliant Lady's Inaugural Season
Only suites remaining
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Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,790$2,546
per Cabin
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5 nights
Valiant Lady
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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
$1,790$2,546
per Cabin
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Departing on:
2025
Fri, Sep 26 - Wed, Oct 01
from (US$)$1,790

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Sea View cabins from
$4,900$7,164
per Cabin
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10 nights
Resilient Lady
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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
$4,900$7,164
per Cabin
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Departing on:
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)$4,900

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
$4,940$7,286
per Cabin
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13 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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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
$4,940$7,286
per Cabin
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Departing on:
2025
Fri, Oct 03 - Thu, Oct 16
from (US$)$4,940Brilliant Lady's Inaugural Season

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,190$1,560
per Cabin
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5 nights
Valiant Lady
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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
$1,190$1,560
per Cabin
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Departing on:
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)$1,190

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
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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
$3,510$5,200
per Cabin
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Departing on:
2025
Tue, Oct 07 - Thu, Oct 16
from (US$)$3,510

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
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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
$1,290$1,774
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,290

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
$3,488$5,038
per Cabin
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7 nights
Resilient Lady
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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
$3,488$5,038
per Cabin
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Departing on:
2025
Sun, Oct 12 - Sun, Oct 19
from (US$)$3,488

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Sea View cabins from
$3,450$5,144
per Cabin
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15 nights
Scarlet Lady
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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
$3,450$5,144
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$3,450
★
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
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
$2,384$3,436
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$)$2,384Brilliant Lady's Inaugural Season

Mykonos Moons to Spanish Sunrises

  • Athens (Piraeus)
  • Mykonos, Greece
  • Catania, Sicily, Italy
  • Palma de Mallorca, Spain
  • Valencia, Spain
  • Barcelona
Sea View cabins from
$3,710$5,442
per Cabin
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7 nights
Resilient Lady
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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
$3,710$5,442
per Cabin
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Departing on:
2025
Sun, Oct 19 - Sun, Oct 26
from (US$)$3,710

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,190$1,550
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
$1,190$1,550
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)$1,190

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,290$1,772
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.
Learn more
70% off second Sailor
Insider cabins from
$1,290$1,772
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)$1,290

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
RockStar Quarters suites from
$11,452
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
RockStar Quarters suites from
$11,452
per Cabin
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Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)$11,452
Only suites remaining
Average starting price per cabin (incl. taxes & fees)