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Explore 399 cruise vacations
Showing Loading cruise vacations: Europe, North America & Caribbean, July 2025 - December 2025
2 Sailors , 1 Cabin
Showing 67 cruise vacations that match your search
Showing 67 cruise vacations that match your search

Grand Cayman, Costa Maya & More
- Miami, Florida
- George Town, Grand Cayman
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Grand Turk, Puerto Plata & More
- Miami, Florida
- Puerto Plata, Dominican Republic
- Grand Turk, Turks and Caicos
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Greek Island Glow
- Athens (Piraeus)
- Santorini, Greece
- Rhodes, Greece
- Bodrum, Turkey
- Mykonos, Greece
- Athens (Piraeus)
70% off 2nd Sailor
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Departing on:

Corfu, Dubrovnik & More
- Athens (Piraeus)
- Kotor, Montenegro
- Dubrovnik, Croatia
- Corfu, Greece
- Mykonos, Greece
- Athens (Piraeus)
70% off 2nd Sailor
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Departing on:
Sun, Jul 27 - Sun, Aug 03
from (US$) Only suites remaining

Fire & Sunset Soirées
- Miami, Florida
- Key West, Florida
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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Departing on:

Reykjavik to Amsterdam & Portsmouth
- Reykjavik
- Reykjavik, Iceland
- Ísafjörður, Iceland
- Akureyri, Iceland
- Lerwick/Shetland, Scotland
- Amsterdam, Netherlands
- Portsmouth
70% off 2nd Sailor

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 2nd Sailor
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Departing on:

Dominican Daze
- Miami, Florida
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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Departing on:

Portsmouth to Ireland, Scotland & More
- Portsmouth
- Amsterdam, Netherlands
- Bruges/Zeebruge (Brussels), Belgium
- Kirkwall, Scotland
- Stornoway, Isle of Lewis, Scotland
- Glasgow (Greenock), Scotland
- Belfast, Northern Ireland
- Dublin, Ireland
- Portsmouth
70% off 2nd Sailor

Riviera Maya
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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Portsmouth to Amsterdam & Bordeaux
- Portsmouth
- Amsterdam, Netherlands
- Bruges/Zeebruge (Brussels), Belgium
- Bordeaux (Le Verdon), France
- Portsmouth
70% off 2nd Sailor

Mayan Sol
- Miami, Florida
- Costa Maya, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor
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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 2nd Sailor

Barcelona to Cannes, Rome & Tuscany
- Barcelona
- Ibiza, Spain
- Palma de Mallorca, Spain
- Cannes, France
- Ajaccio, Corsica, France
- Cagliari, Sardinia, Italy
- Florence/Pisa (Livorno), Italy
- Pompeii/Capri (Naples), Italy
- Rome (Civitavecchia)
70% off 2nd Sailor

Starry Nights in Greece & Croatia
- Athens (Piraeus)
- Santorini, Greece
- Bodrum, Turkey
- Mykonos, Greece
- Dubrovnik, Croatia
- Kotor, Montenegro
- Corfu, Greece
- Athens (Piraeus)
70% off 2nd Sailor

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 2nd Sailor

Brilliant Lady Miami MerMaiden
- Miami, Florida
- Philipsburg, St. Maarten
- Tortola, British Virgin Islands
- The Beach Club at Bimini, Bahamas
- Miami, Florida
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70% off 2nd Sailor
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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 2nd Sailor

Honduras, Mexico & Bahamas
- Miami, Florida
- Roatán, Honduras
- Costa Maya, Mexico
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Western Caribbean: From Miami to Bimini
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
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70% off 2nd Sailor
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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 2nd Sailor

Colorful Curaçao to the Charming Caymans
- Miami, Florida
- Oranjestad, Aruba
- Willemstad, Curaçao
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
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70% off 2nd Sailor
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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 2nd Sailor

Western Caribbean Charm
- Miami, Florida
- Costa Maya, Mexico
- Roatán, Honduras
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

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 2nd Sailor

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 2nd Sailor

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
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70% off 2nd Sailor
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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 2nd Sailor
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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 2nd Sailor
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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
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70% off 2nd Sailor
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Departing on:

San Juan, Samaná & Bimini
- Miami, Florida
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Aruban Sunsets & Calm Cayman Days
- Miami, Florida
- Oranjestad, Aruba
- Cartagena, Colombia
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- Miami, Florida
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70% off 2nd Sailor
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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 2nd Sailor

Brilliant Caribbean Holidays
- Miami, Florida
- Grand Turk, Turks and Caicos
- Puerto Plata, Dominican Republic
- San Juan, Puerto Rico
- Samaná, Dominican Republic
- Miami, Florida
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70% off 2nd Sailor
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Resilient Caribbean Holidays
- Miami, Florida
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

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 2nd Sailor

Scarlet Caribbean Holidays
- Miami, Florida
- Nassau, Bahamas
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

Brilliant New Year's Ahoy!
- Miami, Florida
- Grand Turk, Turks and Caicos
- St. John's, Antigua
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
- Miami, Florida
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70% off 2nd Sailor
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Resilient New Year's Ahoy!
- Miami, Florida
- Ocho Rios, Jamaica
- George Town, Grand Cayman
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor

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 2nd Sailor

Scarlet New Year's Ahoy!
- Miami, Florida
- Cozumel, Mexico
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off 2nd Sailor