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Explore 415 cruise vacations

Showing Loading cruise vacations: All Destinations, May 2026 - May 2026
LIMITED-TIME ONLY:
70% off 2nd Sailor + up to $600* instant savings
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Extra savings on 7+ night Caribbean winter cruises.
Showing 21 cruise vacations that match your search
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★
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
$2,520$3,630
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
Insider cabins from
$2,520$3,630
per Cabin
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Departing on:
2026
Sat, Apr 25 - Sat, May 02
from (US$)$2,520

New York Transatlantic to Spain

  • New York City, New York
  • Ponta Delgada, Azores
  • Funchal, Madeira, Portugal
  • Tangier, Morocco
  • Málaga, Spain
  • Palma de Mallorca, Spain
  • Barcelona
Sea Terrace cabins from
$3,780$5,498
per Cabin
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14 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
$3,780$5,498
per Cabin
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Departing on:
2026
Sat, Apr 25 - Sat, May 09
from (US$)$3,780
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $600* off
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Hollywood Sunsets & Mexican Horizons

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlàn, Mexico
  • Puerto Vallarta, Mexico
  • Los Angeles, California
Sea View cabins from
$3,066$4,460
per Cabin
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7 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 View cabins from
$3,066$4,460
per Cabin
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Departing on:
2026
Sun, Apr 26 - Sun, May 03
from (US$)$3,066Brilliant Lady's Inaugural Season

Transatlantic to Spain & Morocco

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Alicante, Spain
  • Barcelona
Insider cabins from
$3,500$5,218
per Cabin
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14 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
Insider cabins from
$3,500$5,218
per Cabin
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Departing on:
2026
Sun, Apr 26 - Sun, May 10
from (US$)$3,500

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,000$2,872
per Cabin
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5 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
$2,000$2,872
per Cabin
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Departing on:
2026Best Rate
Sat, May 02 - Thu, May 07
from (US$)$2,000
2026
Sat, May 16 - Thu, May 21
from (US$)$2,150
2026
Sat, May 30 - Thu, Jun 04
from (US$)$2,200

LA Lights & Vancouver Vistas

  • Los Angeles, California
  • Catalina Island, California
  • San Francisco, California
  • Astoria, Oregon
  • Victoria, British Columbia
  • Vancouver, British Columbia
Insider cabins from
$2,224$3,128
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
$2,224$3,128
per Cabin
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Departing on:
2026
Sun, May 03 - Mon, May 11
from (US$)$2,224Brilliant Lady's Inaugural Season

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,592$2,242
per Cabin
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4 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
$1,592$2,242
per Cabin
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Departing on:
2026Best Rate
Thu, May 21 - Mon, May 25
from (US$)$1,592
2026
Thu, May 07 - Mon, May 11
from (US$)$1,640

Rome, Mykonos & the Amalfi Coast

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,500$5,136
per Cabin
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7 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
Insider cabins from
$3,500$5,136
per Cabin
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Departing on:
2026
Sun, May 10 - Sun, May 17
from (US$)$3,500

Alaska Awe from Vancouver to Seattle

  • Vancouver, British Columbia
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Skagway, Alaska
  • Juneau, Alaska
  • Icy Strait Point, Alaska
  • Seattle, Washington
Sea View cabins from
$3,980$5,816
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 second Sailor
Sea View cabins from
$3,980$5,816
per Cabin
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Departing on:
2026
Mon, May 11 - Thu, May 21
from (US$)$3,980Brilliant Lady's Inaugural Season

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,790$2,484
per Cabin
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5 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
$1,790$2,484
per Cabin
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Departing on:
2026
Mon, May 11 - Sat, May 16
from (US$)$1,790

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,136$4,546
per Cabin
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7 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
Insider cabins from
$3,136$4,546
per Cabin
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Departing on:
2026Best Rate
Sun, May 17 - Sun, May 24
from (US$)$3,136
2026
Sun, May 31 - Sun, Jun 07
from (US$)$3,136

Brilliant Lady Seattle MerMaiden

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
$2,508$3,544
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
$2,508$3,544
per Cabin
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Departing on:
2026
Thu, May 21 - Thu, May 28
from (US$)$2,508Brilliant Lady's Inaugural Season

Corfu, Dubrovnik & More

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,360$4,924
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
$3,360$4,924
per Cabin
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Departing on:
2026
Sun, May 24 - Sun, May 31
from (US$)$3,360

Amalfi Coast, Cannes & Ibiza

  • Rome (Civitavecchia)
  • Amalfi Coast (Salerno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,300$4,900
per Cabin
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6 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
$3,300$4,900
per Cabin
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Departing on:
2026
Mon, May 25 - Sun, May 31
from (US$)$3,300

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,790$2,548
per Cabin
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5 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
$1,790$2,548
per Cabin
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Departing on:
2026
Mon, May 25 - Sat, May 30
from (US$)$1,790

Seattle, Juneau & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Juneau, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
$3,346$4,822
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
$3,346$4,822
per Cabin
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Departing on:
2026
Thu, May 28 - Thu, Jun 04
from (US$)$3,346Brilliant Lady's Inaugural Season

Spanish Isles, Rome & Cannes

  • Barcelona
  • Palma de Mallorca, Spain
  • Rome (Civitavecchia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,150$4,628
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
Insider cabins from
$3,150$4,628
per Cabin
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Departing on:
2026
Sun, May 31 - Sun, Jun 07
from (US$)$3,150
Average starting price per cabin (incl. taxes & fees)