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Explore 418 cruise vacations

Showing Loading cruise vacations: All Destinations, September 2025 - November 2025
Showing 40 cruise vacations that match your search
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Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,190$1,622
per Cabin
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5 nights
Valiant Lady & Scarlet Lady
+ 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

Portsmouth to Lisbon, Casablanca & Spain

  • Portsmouth
  • La Coruña, Spain
  • Lisbon, Portugal
  • Casablanca, Morocco
  • Málaga, Spain
  • Ibiza, Spain
  • Barcelona
Sea Terrace cabins from
$6,890$10,330
per Cabin
13 nights
Scarlet Lady
+ 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
$6,890$10,330
per Cabin
Departing on:
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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.

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,346$4,822
per Cabin
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7 nights
Resilient Lady
+ 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

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
+ 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
$2,544$3,616
per Cabin
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Departing on:

Istanbul, Santorini & More

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
Sea View cabins from
$5,500$8,034
per Cabin
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11 nights
Resilient Lady
+ 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
$5,500$8,034
per Cabin
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Departing on:
EXTRA SAVINGS

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,090
per Cabin
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5 nights
Valiant Lady & Scarlet Lady
+ 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

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
Sea View cabins from
$2,580$3,658
per Cabin
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ 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
$2,580$3,658
per Cabin
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Departing on:

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
+ 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
$4,300$6,242
per Cabin
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Departing on:

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
+ 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$1,714
per Cabin
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Departing on:

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 View cabins from
$3,582$5,312
per Cabin
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9 nights
Scarlet Lady
+ 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
$3,582$5,312
per Cabin
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Departing on:

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
+ 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
$1,490$2,082
per Cabin
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Departing on:

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
$10,800
per Cabin
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15 nights
Scarlet Lady
+ 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
RockStar Quarters suites from
$10,800
per Cabin
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Departing on:

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
$2,704$3,928
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ 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
$2,704$3,928
per Cabin
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Departing on:

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
+ 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:

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
Loading
5 nights
Valiant Lady
+ 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:

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
Loading
5 nights
Valiant Lady
+ 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
$1,692$2,388
per Cabin
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Departing on:

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
+ 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
RockStar Quarters suites from
$11,452
per Cabin
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Departing on:

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,592$2,226
per Cabin
Loading
4 nights
Valiant Lady
+ 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
$1,592$2,226
per Cabin
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Departing on:
EXTRA SAVINGS

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,654
per Cabin
Loading
7 nights
Scarlet Lady
+ 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
$1,654
per Cabin
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Departing on:

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
$1,806$2,526
per Cabin
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ 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
$1,806$2,526
per Cabin
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Departing on:
EXTRA SAVINGS

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
Insider cabins from
$1,304
per Cabin
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6 nights
Valiant Lady
+ 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
$1,304
per Cabin
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Departing on:

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
$2,856$4,128
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ 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
$2,856$4,128
per Cabin
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Departing on:

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
$3,068$4,558
per Cabin
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7 nights
Valiant Lady
+ 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
$3,068$4,558
per Cabin
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Departing on:
EXTRA SAVINGS

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,640$3,754
per Cabin
Loading
6 nights
Resilient Lady
+ 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
$2,640$3,754
per Cabin
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Departing on:

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,592$2,226
per Cabin
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4 nights
Scarlet Lady
+ 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
EXTRA SAVINGS

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,516
per Cabin
Loading
7 nights
Resilient Lady
+ 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
$1,516
per Cabin
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Departing on:
EXTRA SAVINGS

Sunny Miles of Tropical Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$1,522
per Cabin
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7 nights
Valiant Lady
+ 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
$1,522
per Cabin
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Departing on:
EXTRA SAVINGS

Sunny San Juan & Isles of Beach Miles

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
$1,736
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ 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
$1,736
per Cabin
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Departing on:

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,090$3,016
per Cabin
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5 nights
Scarlet Lady
+ 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

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,806$2,526
per Cabin
Loading
7 nights
Resilient Lady
+ 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
$1,806$2,526
per Cabin
Loading
Departing on:
EXTRA SAVINGS

Thanksgiving in the Lesser Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Insider cabins from
$1,518
per Cabin
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7 nights
Valiant Lady
+ 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
$1,518
per Cabin
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Departing on:

Antigua Waves & Grand Turk Caves

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
$2,142$3,076
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ 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
$2,142$3,076
per Cabin
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Departing on:
EXTRA SAVINGS

San Juan to Barbados & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Roseau, Dominica
  • Bridgetown, Barbados
  • San Juan, Puerto Rico
Insider cabins from
$1,298
per Cabin
Loading
6 nights
Valiant Lady
+ 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
$1,298
per Cabin
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Departing on:
EXTRA SAVINGS

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,522
per Cabin
Loading
7 nights
Resilient Lady
+ 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
$1,522
per Cabin
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Departing on: