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Explore 414 cruise vacations
Showing Loading cruise vacations: All Destinations, September 2025 - November 2025
Showing 37 cruise vacations that match your search
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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
CA$3,570CA$5,074
per Cabin
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8 nights
Brilliant Lady
70% off second Sailor
Insider cabins from
CA$3,570CA$5,074
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 second Sailor
Sea Terrace cabins from
CA$7,377CA$10,749
per Cabin
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Departing on:

Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
CA$1,952CA$2,608
per Cabin
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Departing on:

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
Mega RockStar Quarters suites from
CA$21,863
per Cabin
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10 nights
Brilliant Lady
70% off second Sailor
Mega RockStar Quarters suites from
CA$21,863
per Cabin
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Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (CA$)$21,863Brilliant Lady's Inaugural SeasonOnly suites remaining

Dominican Daze
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
CA$2,512CA$3,564
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 second Sailor
Sea View cabins from
CA$6,875CA$10,053
per Cabin
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Departing on:

Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
CA$1,813CA$2,407
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
70% off second Sailor
Sea Terrace cabins from
CA$8,465CA$12,741
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
70% off second Sailor
Sea View cabins from
CA$2,092CA$2,922
per Cabin
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Departing on:

Greek Island Glow
- Athens (Piraeus)
- Santorini, Greece
- Rhodes, Greece
- Bodrum, Turkey
- Mykonos, Greece
- Athens (Piraeus)
70% off second Sailor
Insider cabins from
CA$5,601CA$8,157
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
70% off second Sailor
RockStar Quarters suites from
CA$13,007
per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (CA$)$13,007Only suites remaining

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UP TO $600 OFF
Brilliant Lady Miami MerMaiden
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- The Beach Club at Bimini, Bahamas
- Miami, Florida
Insider cabins from
CA$3,347CA$4,823
per Cabin
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8 nights
Brilliant Lady
70% off second Sailor
Insider cabins from
CA$3,347CA$4,823
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
70% off second Sailor
Sea Terrace cabins from
CA$5,500CA$8,090
per Cabin
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Departing on:

Riviera Maya: Halloween Edition
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
CA$1,812CA$2,392
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
70% off second Sailor
Sea View cabins from
CA$2,372CA$3,350
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
70% off second Sailor
Sea Terrace cabins from
CA$6,679CA$10,059
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
CA$2,236CA$3,124
per Cabin
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Departing on:

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UP TO $600 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
CA$2,142CA$2,826
per Cabin
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Departing on:

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UP TO $600 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
CA$2,929CA$4,151
per Cabin
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7 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
CA$2,929CA$4,151
per Cabin
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Departing on:

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
CA$1,835CA$2,571
per Cabin
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Departing on:

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UP TO $600 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
CA$4,683CA$6,831
per Cabin
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12 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
CA$4,683CA$6,831
per Cabin
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Departing on:

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UP TO $600 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
Sea Terrace cabins from
CA$4,305CA$6,397
per Cabin
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Departing on:

Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
CA$2,174CA$2,914
per Cabin
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Departing on:

Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Sea View cabins from
CA$2,236CA$3,124
per Cabin
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Departing on:

★
UP TO $600 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
CA$2,337CA$3,253
per Cabin
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Departing on:

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UP TO $600 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
CA$2,535CA$3,689
per Cabin
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Departing on:

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UP TO $600 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
CA$2,897CA$4,171
per Cabin
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8 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
CA$2,897CA$4,171
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 second Sailor
Sea View cabins from
CA$2,512CA$3,584
per Cabin
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Departing on:

★
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
70% off second Sailor
Sea View cabins from
CA$2,535CA$3,545
per Cabin
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Departing on:

★
UP TO $600 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
CA$2,338CA$3,368
per Cabin
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Departing on:

★
UP TO $600 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
Sea View cabins from
CA$3,512CA$5,096
per Cabin
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9 nights
Brilliant Lady
70% off second Sailor
Sea View cabins from
CA$3,512CA$5,096
per Cabin
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Departing on:

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
CA$2,172CA$3,158
per Cabin
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Departing on:

★
UP TO $600 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
CA$2,339CA$3,271
per Cabin
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Departing on:
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