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Explore 416 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - October 2025
1 Sailor , 1 Cabin
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Showing 16 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 Terrace cabins from
$2,769$6,372
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
$2,769$6,372
per Cabin
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Departing on:
2025Best Rate
Sun, Oct 12 - Sun, Oct 19
from (US$)$2,769
2025
Sun, Sep 14 - Sun, Sep 21
from (US$)$3,044

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
$2,268$3,341
per Cabin
8 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
Insider cabins from
$2,268$3,341
per Cabin
Departing on:
2025
Mon, Sep 15 - Tue, Sep 23
from (US$)$2,268Brilliant 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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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
$10,801
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 second Sailor
RockStar Quarters suites from
$10,801
per Cabin
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Departing on:
2025
Sun, Sep 21 - Thu, Oct 02
from (US$)$10,801
Only suites remaining

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$941$1,313
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
$941$1,313
per Cabin
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Departing on:
2025
Sun, Sep 21 - Fri, Sep 26
from (US$)$941

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
Insider cabins from
$1,700
per Cabin
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10 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
Insider cabins from
$1,700
per Cabin
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Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (US$)$1,700Brilliant Lady's Inaugural Season

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,307$3,444
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
Sea Terrace cabins from
$2,307$3,444
per Cabin
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Departing on:
2025
Fri, Sep 26 - Wed, Oct 01
from (US$)$2,307

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
$3,954$5,896
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
$3,954$5,896
per Cabin
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Departing on:
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)$3,954

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,039$1,463
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
$1,039$1,463
per Cabin
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Departing on:
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)$1,039

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
$3,044$6,540
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
Sea Terrace cabins from
$3,044$6,540
per Cabin
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Departing on:
2025
Tue, Oct 07 - Thu, Oct 16
from (US$)$3,044

True Crime Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,201$2,670
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
$1,201$2,670
per Cabin
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Departing on:
2025
Fri, Oct 10 - Wed, Oct 15
from (US$)$1,201

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
$10,649
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
RockStar Quarters suites from
$10,649
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$10,649
Only suites remaining
★
EXTRA SAVINGS

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,489$3,713
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 second Sailor
Sea View cabins from
$2,489$3,713
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$)$2,489Brilliant 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
$3,675$5,521
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.
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70% off second Sailor
Sea Terrace cabins from
$3,675$5,521
per Cabin
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Departing on:
2025
Sun, Oct 19 - Sun, Oct 26
from (US$)$3,675

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,030$1,444
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
$1,030$1,444
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)$1,030

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,420$3,206
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
Sea Terrace cabins from
$1,420$3,206
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)$1,420
Average starting price per cabin (incl. taxes & fees)