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Explore 405 cruise vacations
Showing Loading cruise vacations: All Destinations, October 2025 - December 2025
Showing 44 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)
70% off second Sailor

Scarlet's Haunted Halloween Soirée
- Barcelona
- Palma de Mallorca, Spain
- Casablanca, Morocco
- Funchal, Madeira, Portugal
- Santa Cruz de Tenerife, Spain
- Miami, Florida
70% off second Sailor
RockStar Quarters suites from
$9,270
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$9,270Only suites remaining

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UP TO $700 OFF
Brilliant Lady Miami MerMaiden
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Sea Terrace cabins from
$2,704$3,928
per Cabin
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8 nights
Brilliant Lady
70% off second Sailor
Sea Terrace cabins from
$2,704$3,928
per Cabin
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Riviera Maya: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,390$1,858
per Cabin
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Dominican Daze: Halloween Edition
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,540$2,154
per Cabin
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Resilient's Haunted Halloween Soirée
- Barcelona
- Valencia, Spain
- Casablanca, Morocco
- Las Palmas de Gran Canaria, Spain
- Miami, Florida
70% off second Sailor
Sea Terrace cabins from
$3,070$4,566
per Cabin
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Valiant's Haunted Halloween Soirée
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,352$1,856
per Cabin
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UP TO $700 OFF
Scarlet's Haunted Halloween Soirée
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,386$1,798
per Cabin
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UP TO $700 OFF
Western Caribbean: From Miami to Bimini
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Sea View cabins from
$2,086$2,956
per Cabin
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7 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
$2,086$2,956
per Cabin
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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
70% off second Sailor
Insider cabins from
$1,188$1,648
per Cabin
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Dominican Daze
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,190$1,618
per Cabin
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UP TO $700 OFF
Colorful Curaçao to the Charming Caymans
- Miami, Florida
- Oranjestad, Aruba
- Willemstad, Curaçao
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
Sea View cabins from
$3,336$4,866
per Cabin
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12 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
$3,336$4,866
per Cabin
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Departing on:

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UP TO $700 OFF
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
70% off second Sailor
Insider cabins from
$1,806$2,618
per Cabin
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Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea Terrace cabins from
$1,548$2,076
per Cabin
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Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,272$1,734
per Cabin
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Departing on:

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UP TO $700 OFF
San Juan Sunrises & Dominican Dreams
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,386$1,888
per Cabin
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UP TO $700 OFF
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
70% off second Sailor
Sea View cabins from
$1,526$2,198
per Cabin
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Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,190$1,550
per Cabin
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UP TO $700 OFF
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
Sea View cabins from
$2,224$3,218
per Cabin
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8 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
$2,224$3,218
per Cabin
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Miami, Grand Turk (& back)
- Miami, Florida
- Grand Turk, Turks and Caicos
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$1,590$2,242
per Cabin
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UP TO $700 OFF
Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,386$1,880
per Cabin
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UP TO $700 OFF
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
70% off second Sailor
Insider cabins from
$1,476$2,108
per Cabin
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UP TO $700 OFF
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
70% off second Sailor
Insider cabins from
$2,142$3,076
per Cabin
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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
70% off second Sailor
Sea View cabins from
$1,308$1,882
per Cabin
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UP TO $700 OFF
San Juan, Samaná & Bimini
- Miami, Florida
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,386$1,900
per Cabin
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UP TO $700 OFF
Nicky Jam x Virgin Voyages
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- Roseau, Dominica
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$1,744$2,520
per Cabin
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UP TO $700 OFF
Aruban Sunsets & Calm Cayman Days
- Miami, Florida
- Oranjestad, Aruba
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
Insider cabins from
$2,618$3,784
per Cabin
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11 nights
Brilliant Lady
70% off second Sailor
Insider cabins from
$2,618$3,784
per Cabin
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Departing on:

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UP TO $700 OFF
Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea Terrace cabins from
$1,806$2,526
per Cabin
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Departing on:

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UP TO $700 OFF
St. Lucia, St. Maarten, Barbados & More
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Roseau, Dominica
- Bridgetown, Barbados
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$1,942$2,838
per Cabin
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UP TO $700 OFF
Brilliant Caribbean Holidays
- Miami, Florida
- Grand Turk, Turks and Caicos
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- Miami, Florida
Sea View cabins from
$2,544$3,714
per Cabin
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8 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
$2,544$3,714
per Cabin
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Departing on:

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UP TO $700 OFF
Resilient Caribbean Holidays
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$2,750$3,984
per Cabin
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UP TO $700 OFF
Valiant Caribbean Holidays
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,946$2,834
per Cabin
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Scarlet Caribbean Holidays
- Miami, Florida
- Nassau, Bahamas
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea Terrace cabins from
$1,912$2,734
per Cabin
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UP TO $700 OFF
Brilliant New Year's Ahoy!
- Miami, Florida
- Grand Turk, Turks and Caicos
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
- Miami, Florida
Insider cabins from
$4,462$6,678
per Cabin
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9 nights
Brilliant Lady
70% off second Sailor
Insider cabins from
$4,462$6,678
per Cabin
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Departing on:

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UP TO $700 OFF
Resilient New Year's Ahoy!
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$3,906$5,756
per Cabin
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Departing on:

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UP TO $700 OFF
Valiant New Year’s Ahoy!
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Bridgetown, Barbados
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$3,936$5,916
per Cabin
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Scarlet New Year's Ahoy!
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
$3,290$4,780
per Cabin
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