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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
70% off a second Sailor
Insider cabins from
$1,190$1,622
per Cabin
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Departing on:

Portsmouth to Lisbon, Casablanca & Spain
- Portsmouth
- La Coruña, Spain
- Lisbon, Portugal
- Casablanca, Morocco
- Málaga, Spain
- Ibiza, Spain
- Barcelona
70% off a second Sailor
Sea Terrace cabins from
$6,890$10,330
per Cabin
Departing on:

Greek Island Glow
- Athens (Piraeus)
- Santorini, Greece
- Rhodes, Greece
- Bodrum, Turkey
- Mykonos, Greece
- Athens (Piraeus)
70% off a second Sailor
Insider cabins from
$3,346$4,822
per Cabin
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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
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)
70% off a second Sailor
Sea View cabins from
$5,500$8,034
per Cabin
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EXTRA SAVINGS
Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Insider cabins from
$1,090
per Cabin
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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
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)
70% off a second Sailor
Sea View cabins from
$4,300$6,242
per Cabin
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Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Insider cabins from
$1,290$1,714
per Cabin
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Italy to France & Spain
- Rome (Civitavecchia)
- Cagliari, Sardinia, Italy
- Tuscany/Cinque Terre (Marina di Carrara), Italy
- Ajaccio, Corsica, France
- Cannes, France
- Valencia, Spain
- Barcelona
70% off a second Sailor
Sea View cabins from
$3,582$5,312
per Cabin
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True Crime Voyage
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Sea View cabins from
$1,490$2,082
per Cabin
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Scarlet's Haunted Halloween Soirée
- Barcelona
- Palma de Mallorca, Spain
- Casablanca, Morocco
- Funchal, Madeira, Portugal
- Santa Cruz de Tenerife, Spain
- Miami, Florida
70% off a second Sailor
RockStar Quarters suites from
$10,800
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)$10,800Only suites remaining

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
70% off a second Sailor
Sea View cabins from
$2,704$3,928
per Cabin
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Mykonos Moons to Spanish Sunrises
- Athens (Piraeus)
- Mykonos, Greece
- Catania, Sicily, Italy
- Palma de Mallorca, Spain
- Valencia, Spain
- Barcelona
70% off a second Sailor
Sea Terrace cabins from
$3,920$5,766
per Cabin
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Riviera Maya: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Insider cabins from
$1,290$1,704
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 a second Sailor
Sea View cabins from
$1,692$2,388
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 a second Sailor
RockStar Quarters suites from
$11,452
per Cabin
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Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)$11,452Only suites remaining

Valiant's Haunted Halloween Soirée
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Sea View cabins from
$1,592$2,226
per Cabin
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Departing on:

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EXTRA SAVINGS
Scarlet's Haunted Halloween Soirée
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Sea View cabins from
$1,654
per Cabin
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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
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7 nights
Brilliant Lady
70% off a second Sailor
Insider cabins from
$1,806$2,526
per Cabin
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Departing on:

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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
70% off a second Sailor
Insider cabins from
$1,304
per Cabin
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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
70% off a second Sailor
Insider cabins from
$2,856$4,128
per Cabin
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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 a second Sailor
Sea Terrace cabins from
$3,068$4,558
per Cabin
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EXTRA SAVINGS
Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Sea View cabins from
$2,640$3,754
per Cabin
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Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Sea View cabins from
$1,592$2,226
per Cabin
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Departing on:

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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
70% off a second Sailor
Insider cabins from
$1,516
per Cabin
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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
70% off a second Sailor
Insider cabins from
$1,522
per Cabin
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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
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
70% off a second Sailor
Sea Terrace cabins from
$2,090$3,016
per Cabin
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Cayman Coves & Jamaican Waterfalls
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Sea View cabins from
$1,806$2,526
per Cabin
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Departing on:

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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
70% off a second Sailor
Insider cabins from
$1,518
per Cabin
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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 a second Sailor
Insider cabins from
$2,142$3,076
per Cabin
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Departing on:

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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
70% off a second Sailor
Insider cabins from
$1,298
per Cabin
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EXTRA SAVINGS
San Juan, Samaná & Bimini
- Miami, Florida
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off a second Sailor
Insider cabins from
$1,522
per Cabin
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