Sicily Sailing Cruises

from $8,910

No SS

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Epicurean Delights: The Food & Wine of Sicily

Valletta Roundtrip - 9 Day Itinerary aboard Le Dumont-d'Urville

• Visit Valley of Temples
• Walk Palermo’s historic streets
• Visit Taormina’s Greco-Roman theatr
• Wander Syracuse’s old town

Starts / Ends

Valletta / Valletta

Activities

Local Market Visits

Activity Level

Variable

Sail roundtrip from Valletta on a 9-day cruise through Sicily aboard Le Dumont-d’Urville. Discover Palermo, Syracuse, Taormina, and more as you explore UNESCO-listed ruins, charming island villages, and volcanic landscapes rich in history and culture.

Cruise Details

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from $14,158

Save 20%

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The Ancient Shores of Sicily and Malta

Roundtrip Malta - 10 Day Itinerary aboard Sea Cloud II

• Explore stunning UNESCO-listed site
• Step into the history of Sicily
• Discover the charm of ancient Erice
• Savor the authentic Sicily flavors
• Explore historic Taormina and Sirac

Starts / Ends

Valletta / Valletta

Activities

Wine Tasting

Activity Level

Variable

Embark on a 10-day Ancient Shores of Sicily and Malta cruise, aboard Sea Cloud II. Explore ancient cities, UNESCO-listed temples, and landscapes shaped by the Romans, Greeks, and Carthaginians. Visit Agrigento’s Valley of the Temples, the Ggantija Temples, and Valletta, stroll medieval Erice, and tour The Godfather’s Castello degli Schiavi.

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from $3,218

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The Best of the Mediterranean

Roundtrip Valletta - 8 Day Itinerary aboard MV La Belle de L'Adriatique

• Explore Saint John's Baroque
• Taste chocolate in Modica
• Ascend mighty Mount Etna
• Stroll Mdina’s medieval streets

Starts / Ends

Valletta / Valletta

Activity Level

Variable

Discover the best of the Mediterranean as you explore the magic of Malta and Sicily on an 8-day cruise aboard La Belle de l’Adriatique, featuring UNESCO sites, historic towns, and local flavors. From Valletta to Syracuse, enjoy every excursions, cultural treasures, and vibrant onboard festivities.

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from $12,795

EBD

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The Amalfi, Sicily and Malta: The Godfather

Rome - Valletta - 12 Day Itinerary aboard Douglas Mawson

• Discover Rome’s imperial relics
• Explore Gaeta’s medieval fortress
• Wander Naples’ ancient streets
• Marvel at Pompeii’s ruins

Starts / Ends

Rome / Valletta

Activity Level

Variable

Join this 12-day cruise on the Douglas Mawson, exploring Southern Italy, Sicily, and Malta's stunning history and culture. Experience the Amalfi Coast, ancient cities, and Malta's heritage while savoring local cuisine and vibrant Mediterranean life.

Cruise Details

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from $2,080

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Amalfi & Sicily

Civitavecchia Roundtrip - 7 Day Itinerary aboard Star Clipper

• Explore Civitavecchia wonders
• Discover Lipari lively streets
• Witness Stromboli’s volcano
• Experience Amalfi seaside views

Starts / Ends

Civitavecchia / Civitavecchia

Activity Level

Variable

Embark on a 7-day cruise aboard the Star Clipper, starting from Civitavecchia and visiting Italy's beautiful coastal spots like the Aeolian Islands and Amalfi. Conclude your journey with easy access to explore Rome.

Cruise Details

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from $7,150

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Ancient Cities of the Mediterranean

Valletta - Athens - 9 Day Itinerary aboard Le Bougainville

• Explore ancient Syracuse ruins
• Tour Sparta’s ancient port
• Wander Monemvasia’s medieval alleys
• Climb Nafplion’s hill fortress

Starts / Ends

Valletta / Athens

Activity Level

Variable

Embark on a 9-day Ancient Cities of the Mediterranean cruise from Valletta to Athens, exploring Syracuse, Reggio di Calabria, Gallipoli, Parga, Gythio, Monemvasia, and Nafplion. Discover a mix of ancient ruins, medieval towns, and coastal views aboard Le Bougainville. Each stop offers insight into centuries of Mediterranean culture and heritage.

Cruise Details

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from $1,710

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Sicily & Greece

Valletta - Piraeus - 6 Day Itinerary aboard Star Flyer

• Explore Valletta’s peninsula
• Discover Syracuse’s vast ruins
• Visit Pilos’ ancient palace
• Enjoy cafes in Monemvasia

Starts / Ends

Valletta / Piraeus

Activity Level

Variable

Embark on a 6-day cruise from Valletta to Athens aboard the Star Flyer, exploring Sicily's archaeological wonders and Greece's historic sites. Experience relaxation at sea and visit ancient locales like Pilos and Monemvasia before concluding your journey in Piraeus.

Cruise Details

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from $11,425

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Early Summer Mediterranean Style

Valletta - Nice - 11 Day Itinerary aboard Sea Cloud Spirit

• Discover Valletta's architecture
• Experience Ortigia’s Old Town
• Explore Corsica, Sardinia and Calvi
• Discover Amalfi and Amalfi Coast

Starts / Ends

Valletta / Nice

Activity Level

Variable

Sail from Malta to France on an 11-day Early Summer Mediterranean cruise aboard the Sea Cloud Spirit. Visit Valletta’s historic streets, Syracuse’s ancient ruins, and Taormina’s views of Mount Etna. Cruise past the Amalfi Coast, visit Capri’s grottos, Corsica’s cliffs, Sardinia’s Catalan past, and Calvi’s beaches. End in St. Tropez and scenic Nice.

Cruise Details

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from $3,610

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Rome to Athens

Civitavecchia - Piraeus - 12 Day Itinerary aboard Star Clipper

• Explore Ponza’s harbor town
• Discover Sorrento’s ancient cliffs
• View Lipari’s bustling marina
• Wander Syracuse’s baroque piazzas

Starts / Ends

Civitavecchia / Piraeus

Activity Level

Variable

Join a 12-day cruise on the Star Clipper, starting from Civitavecchia and exploring Italy's Pontine Islands, the Aeolian Islands, and Sicily. Discover Greece's historic sites, including Olympia and picturesque Hydra, before concluding in Athens.

Cruise Details

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from $2,320

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Amalfi & Sicily

Civitavecchia Roundtrip - 8 Day Itinerary aboard Star Clipper

• Sail across Mediterranean waters
• Visit Lipari for coastal views
• Explore Messina cathedral clock
• See seaside cliffs near Sorrento

Starts / Ends

Civitavecchia / Civitavecchia

Activities

Urban Exploration

Activity Level

Variable

Experience an 8-day Mediterranean sailing adventure from Civitavecchia, exploring Sicily, the Amalfi Coast, and the Aeolian and Pontine Islands aboard Star Clipper. Sail past Stromboli’s active volcano, wander historic Messina, and admire the coastal beauty of Amalfi and Sorrento. Explore Ponza’s unspoiled charm before returning to Rome’s port.

Cruise Details

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from $3,870

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Italy, Montenegro & Croatia

Venice - Civitavecchia - 12 Day Itinerary aboard Royal Clipper

• Admire Venice’s domes
• Wander Rovinj’s medieval streets
• Discover Sibenik’s coastal lanes
• Explore Kotor’s medieval town

Starts / Ends

Venice / Civitavecchia

Activities

Snorkeling

Activity Level

Variable

Set sail on a 12-day Royal Clipper cruise through the Mediterranean, visiting stunning destinations like Venice, Dubrovnik, and Syracuse. Experience rich history and culture while enjoying scenic views and a relaxing day at sea before concluding in Civitavecchia, near Rome.

Cruise Details

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from $5,920

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Ancient Cities of the Mediterranean

Athens - Valletta - 8 Day Itinerary aboard Le Dumont-d'Urville

• Explore ancient Athens landmarks
• Walk Nafplion’s fortress paths
• Discover Corfu’s old town
• Tour Valletta’s historic streets

Starts / Ends

Athens / Valletta

Activity Level

Variable

Sail from Athens to Valletta on an 8-day cruise aboard Le Dumont-d’Urville. Visit Nafplion, Monemvasia, Gythio, Corfu, Gallipoli, and Syracuse. From ancient fortresses and neoclassical towns to volcanic coasts and baroque streets, explore the deep cultural heritage of Greece, Italy, and Malta along the Ionian and Aegean seas.

Cruise Details

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from $11,795

EBD

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Valletta to Venice: An Adriatic Renaissance

Valletta - Venice - 12 Day Itinerary aboard Douglas Mawson

• Unveil Valletta’s history
• Wander Reggio Calabria's sea views
• Uncover Gallipoli’s coastal charm
• Visit Bari’s unique Trulli Houses

Starts / Ends

Malta / Venice

Activity Level

Variable

Join a 12-day cruise on the Douglas Mawson, exploring historic routes from Valletta to Venice. Discover the rich legacies of knights and explorers in cities like Split, Dubrovnik, and Ravenna while experiencing the Adriatic's history and culture.

Cruise Details

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from $8,470

Save 10%

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Isle of Beauty, Italian shores & Malta

Nice - Valletta - 11 Day Itinerary aboard Le Dumont-d'Urville

• Stroll Promenade des Anglais
• Explore Napoleon’s exile home
• Visit Lipari’s obsidian quarries
• See Valletta’s Grandmasters Palace

Starts / Ends

Nice / Valletta

Activities

Spa Relaxation

Activity Level

Variable

Embark on this 11-day cruise across the Mediterranean from Nice to Valletta aboard Le Dumont-d'Urville. Explore Corsica’s charming ports, Sicily’s historical treasures, and the natural beauty of the Aeolian Islands. Visit iconic landmarks like the Calvi Citadel, Portofino’s harbor, and Lipari’s obsidian quarries.

Cruise Details

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from $2,990

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Malta, Balearics & Spain

Valletta - Malaga - 10 Day Itinerary aboard Star Clipper

• Explore Valletta with its heritage
• Discover Porto Empedocle
• Visit Cagliari and its Castello
• Experience Ibiza with its beaches

Starts / Ends

Valletta / Malaga

Activities

Small Ship Sailing, Archaeological Site Visits, Village Visits

Activity Level

Variable

Embark on a 10-day sailing cruise from Valletta to Malaga, visiting Sicily, Sardinia, Menorca, Ibiza, and Cartagena. Explore historic landmarks and enjoy relaxing days at sea on Star Clippers’ tall ships.

Cruise Details

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from $3,610

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Italy, Montenegro and Croatia

Venice - Civitavecchia - 12 Day Itinerary aboard Star Clipper

• Explore Venice’s Grand Canal
• Discover Mali Losinj’s Cikat Bay
• Visit Sibenik’s St. James Cathedral
• Walk Dubrovnik’s ancient city walls

Starts / Ends

Venice / Civitavecchia

Activity Level

Variable

Set sail on a 12-day Star Clipper cruise from Venice, exploring Croatia's coastal gems and Montenegro's Kotor. Discover Italy's Apulia region, Sicily's Taormina, and end your journey in Civitavecchia, just outside Rome.

Cruise Details

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from $4,480

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Grand Voyage: Venice to Rome

Venice - Civitavecchia - 15 Day Itinerary aboard Royal Clipper

• Admire Venice’s Renaissance palaces
• Explore Rovinj’s harbor
• Discover Sibenik’s cathedral
• Walk Dubrovnik’s historic walls

Starts / Ends

Venice / Civitavecchia

Activity Level

Variable

Embark on a 15-day cruise from Venice to Civitavecchia aboard the Royal Clipper, exploring stunning Adriatic and Mediterranean destinations. Discover historical sites in Rovinj, Dubrovnik, and Syracuse while enjoying the natural beauty of islands like Ponza and Corsica.

Cruise Details

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from $7,599

Save 30%

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Adriatic Sunsets

Venice to Rome - 12 Day Itinerary aboard World Traveller

• Explore Venice's Grand Canals
• Taste Otranto’s Regional Wine
• Visit Lipari’s Thermal Springs
• Discover Rome’s Ancient Ruins

Starts / Ends

Venice / Civitavecchia

Activity Level

Variable

Sail the Adriatic and Mediterranean on this 12-day cruise from Venice to Rome aboard World Traveller. Explore the historic beauty of Slovenia’s Piran and Croatia’s charming ports, including Rovinj, Hvar, and Dubrovnik. Cross into Italy and uncover hidden gems like Otranto and Lipari before experiencing the iconic Amalfi Coast, Capri, and Ponza.

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