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Explore 419 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - October 2025
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Select Caribbean sailings from $109 pp/pn
Showing 21 cruise vacations that match your search
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Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
$3,766$5,468
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 a second Sailor
Sea View cabins from
$3,766$5,468
per Cabin
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Departing on:
2025Best Rate
Sun, Oct 12 - Sun, Oct 19
from (US$)$3,766
2025
Sun, Sep 14 - Sun, Sep 21
from (US$)$3,850

Fall Colors: Coastal Northeast & Canada

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • New York City, New York
Insider cabins from
$2,544$3,616
per Cabin
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8 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 a second Sailor
Insider cabins from
$2,544$3,616
per Cabin
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Departing on:
2025
Mon, Sep 15 - Tue, Sep 23
from (US$)$2,544Brilliant Lady's Inaugural Season
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70% off a 2nd Sailor + up to $500 off
Savings on new Brilliant Lady voyages, Europe, Caribbean and more through 2027.
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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
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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 a second Sailor
Insider cabins from
$1,032$1,368
per Cabin
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Departing on:
2025
Wed, Sep 17 - Sun, Sep 21
from (US$)$1,032

Istanbul, Santorini & More

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
RockStar Quarters suites from
$11,198
per Cabin
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11 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 a second Sailor
RockStar Quarters suites from
$11,198
per Cabin
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Departing on:
2025
Sun, Sep 21 - Thu, Oct 02
from (US$)$11,198
Only suites remaining
★
EXTRA SAVINGS

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,190$1,562
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 a second Sailor
Insider cabins from
$1,190$1,562
per Cabin
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Departing on:
2025
Sun, Sep 21 - Fri, Sep 26
from (US$)$1,190

Autumn Leaves: New York to Quebec

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • Quebec City, Quebec
Sea View cabins from
$2,580$3,658
per Cabin
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10 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 a second Sailor
Sea View cabins from
$2,580$3,658
per Cabin
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Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (US$)$2,580Brilliant Lady's Inaugural Season

Barcelona to Cannes, Rome & Tuscany

  • Barcelona
  • Ibiza, Spain
  • Palma de Mallorca, Spain
  • Cannes, France
  • Ajaccio, Corsica, France
  • Cagliari, Sardinia, Italy
  • Florence/Pisa (Livorno), Italy
  • Pompeii/Capri (Naples), Italy
  • Rome (Civitavecchia)
Sea Terrace cabins from
$4,776$7,114
per Cabin
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12 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 a second Sailor
Sea Terrace cabins from
$4,776$7,114
per Cabin
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Departing on:
2025
Thu, Sep 25 - Tue, Oct 07
from (US$)$4,776

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,600$3,790
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 a second Sailor
Sea Terrace cabins from
$2,600$3,790
per Cabin
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Departing on:
2025
Fri, Sep 26 - Wed, Oct 01
from (US$)$2,600

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
$4,300$6,242
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 a second Sailor
Sea View cabins from
$4,300$6,242
per Cabin
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Departing on:
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)$4,300

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
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 a second Sailor
Insider cabins from
$1,290$1,714
per Cabin
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Departing on:
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)$1,290

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
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 a 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
Sea View cabins from
$1,490$2,082
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 a second Sailor
Sea View cabins from
$1,490$2,082
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,490

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Sea Terrace cabins from
$3,570$5,328
per Cabin
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15 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 a second Sailor
Sea Terrace cabins from
$3,570$5,328
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$3,570

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.
Learn more
70% off a 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 Terrace cabins from
$3,920$5,766
per Cabin
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7 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 a second Sailor
Sea Terrace cabins from
$3,920$5,766
per Cabin
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Departing on:
2025
Sun, Oct 19 - Sun, Oct 26
from (US$)$3,920

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
BOOK NOW
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off a second Sailor
Insider cabins from
$1,290$1,704
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)$1,290

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,692$2,388
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 a second Sailor
Sea View cabins from
$1,692$2,388
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)$1,692

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
RockStar Quarters suites from
$11,900
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 a second Sailor
RockStar Quarters suites from
$11,900
per Cabin
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Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)$11,900
Only suites remaining

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,752$2,472
per Cabin
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4 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 a second Sailor
Sea View cabins from
$1,752$2,472
per Cabin
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)$1,752
★
EXTRA SAVINGS

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
$1,514
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.
Learn more
70% off a second Sailor
Insider cabins from
$1,514
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)$1,514
Average starting price per cabin (incl. taxes & fees)