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Sicily Sailing Cruises

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Experience the wonders of Italy, Montenegro, and Croatia on a small ship sailing adventure with Adventure Life this year. Explore the heavenly scent of lavender in the fields of Hvar, witness the awe-inspiring beauty of Dubrovnik, and sail through the narrow Strait of Otranto. From archaeological site visits to snorkeling excursions and optional tours to Pompeii, this cruise offers a relaxed pace suitable for all travelers. Delight in the charming cobbled villages, grand cathedrals, and breathtaking landscapes of the Eastern Mediterranean. Don't miss this opportunity to immerse yourself in the cultural and natural treasures of this enchanting region. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Sicily
Relax in beautiful Sicily
from $8,490
EXPLORE

Longing for La Dolce Vita

Sicily - Italy - 8 Day Itinerary aboard Sea Cloud Spirit
  • Visit Taormina
  • Discover Palermo
  • Explore Lipari
  • Explore Amalfi
Starts / Ends
Catania / Naples
Activity Level
Variable
Embark on an 8-day "Longing for La Dolce Vita" cruise aboard the Sea Cloud Spirit. Begin in Taormina, a town known for its blend of cultures and varied cuisine. Explore Palermo and discover its historic palazzi and gold mosaics, then head to Lipari, an island with volcanic landscapes and a lively harbor town. The trip concludes in Amalfi.
Cruise Details
0
Cruise into charming Sicily
from $2,460
EXPLORE

Amalfi & Sicily

Roundtrip Civitavecchia - 8 Day Itinerary aboard Royal Clipper
  • Explore Civitavecchia seaport hub
  • Wander Sorrento’s cliffside lanes
  • Visit Pompeii’s preserved ruins
  • Admire Amalfi’s medieval Duomo
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Set sail on an 8-day cruise aboard the Royal Clipper, exploring Italy and Sicily with stops in Civitavecchia, Sorrento, Amalfi, Taormina, and Syracuse. Enjoy volcanic views at the Aeolian Islands and optional excursions to Pompeii while experiencing Mediterranean beauty and history.
Cruise Details
0
Sicilian landscape in the early evening
from $2,080
EXPLORE

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
0
Coast of Ortigia island at city of Syracuse
from $2,590
EXPLORE

Sicily & Greece

Piraeus - Valletta - 9 Day Itinerary aboard Star Clipper
  • Explore Piraeus port city
  • Wander Nafplio charming town
  • Discover Monemvasia fortress
  • Visit Syracuse ruins
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Set sail on a 9-day cruise with Star Clipper, exploring Greece, Sicily, and Malta. Discover ancient sites, stunning landscapes, and cultural gems from Athens to Valletta while enjoying the charm of your ship.
Cruise Details
0
Visit Rome's famed Colosseum
from $12,795
EBD
EXPLORE

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
0
Beautiful Taormina, Italy, with Mt. Etna in the background
from $9,920
EXPLORE

Epicurean Delights of Sicily and the Adriatic Coast of Italy

Valletta to Venice - 9 Day Itinerary aboard Le Bougainville
  • Visit Valletta's UNESCO sites
  • Explore ancient Syracuse ruins
  • Visit Taormina's Greek Theater
  • Savor Apulian wine and food
  • Discover Venice’s hidden gardens
  • Enjoy Ravenna's stunning mosaics
  • Mount Etna wine tasting
Starts / Ends
Valletta / Venice
Activities
Wine Tasting
Activity Level
Variable
Embark on a 9-day Le Bougainville trip through Sicily and Italy’s Adriatic coast, visiting UNESCO sites like Valletta, Syracuse, and Venice. Explore ancient ruins, Baroque cities, and medieval towns, while enjoying local wines, cheeses, and dishes prepared by chef Denny Imbroisi.
Cruise Details
0
View of Valletta
from $1,710
EXPLORE

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
Activities
Archaeological Site Visits, Small Ship Sailing
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
0
Relax in beautiful Sicily
from $3,610
EXPLORE

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
Activities
Village Visits
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
0
Beautiful Amalfi Coast
from $2,120
EXPLORE

Amalfi & Sicily

Roundtrip Civitavecchia - 7 Day Itinerary aboard Royal Clipper
  • Explore Civitavecchia seaport hub
  • Discover Sorrento coastal vistas
  • Experience Amalfi medieval port
  • Wander Ponza harbor town
Starts / Ends
Civitavecchia / Civitavecchia
Activity Level
Variable
Set sail on a 7-day cruise from Civitavecchia aboard the Royal Clipper, discovering Italy's stunning coastal towns and historic sites. Explore Sorrento, Amalfi, Taormina, and the Aeolian Islands, all while enjoying breathtaking landscapes and local charm.
Cruise Details
0
View from mount Solaro of Capri island at summer day, Italy
from $10,280
EXPLORE

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
0
Explore Sibenik on the Dalmatian Coast
from $3,870
EXPLORE

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
0
Stop in Piraeus, the port of Athens
from $11,590
2for1
EXPLORE

Pearls of Italy and Greece with the Corinth Canal

Athens - Civitavecchia - 8 Day Itinerary aboard Emerald Sakara
  • Navigate Corinth Canal’s waterway
  • Explore Itea’s coastal charm
  • Discover Fiskardo’s Venetian style
  • Wander Gallipoli’s Old Town
Starts / Ends
Athens / Civitavecchia
Activity Level
Variable
Set sail on an 8-day cruise from Athens to Civitavecchia aboard the Emerald Sakara, discovering Greece and Italy's stunning coasts. Enjoy scenic views, traditional cuisine, and charming ports, culminating in Civitavecchia, your gateway to Rome.
Cruise Details
0
Civitavecchia, the historic port city that opens the gateway to Rome.
from $3,610
EXPLORE

Italy, Montenegro and Croatia

Civitavecchia - Venice - 12 Day Itinerary aboard Star Clipper
  • Explore Ponza’s colorful harbor
  • Discover Amalfi’s grand Duomo
  • Admire Lipari’s volcanic beauty
  • Wander Taormina’s ancient lanes
Starts / Ends
Civitavecchia / Venice
Activity Level
Variable
Set sail on a 12-day cruise from Civitavecchia to Venice on the Star Clipper, exploring Italy and Croatia's hidden gems like Ponza and Otranto. Experience historic towns and local cuisine, and enjoy onboard relaxation and adventure across beautiful coastal seas.
Cruise Details
0
View from gondola during the ride through the canals, Venice
from $3,610
EXPLORE

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
Activities
Local Market Visits
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
0
Relax by the sea in sunny Nice
from $7,990
EXPLORE

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
0
Wander the cobbled streets of Rovinj
from $11,795
EBD
EXPLORE

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
0
Wander through Rome
from $4,600
EXPLORE

Grand Voyage: Venice to Rome

Venice - Civitavecchia - 16 Day Itinerary aboard Royal Clipper
  • Glide in a gondola in Grand Canal
  • Explore ruins and architecture
  • Swim in Dubrovnik's waters
  • Join an optional tour to Pompeii
Starts / Ends
Venice / Civitavecchia
Activity Level
Variable
On this 16-day Grand Voyage cruise from Venice to Rome, explore the waters across Hvar, Dubrovnik, Civitavecchia, East Corsica, and more. Discover the culture and the beauty of the Mediterranean!
Cruise Details
0
Cruise into charming Sicily
from $4,500
EXPLORE

Grand Voyage: Venice to Rome

17 Day Itinerary aboard Star Flyer
  • Explore Venice's canals
  • Explore ruins and architecture
  • Swim in Dubrovnik's waters
  • Join an optional tour to Pompeii
Starts / Ends
Venice / Civitavecchia
Activity Level
Variable
Embark on a 17-day Grand Voyage from Venice to Rome aboard the Star Flyer. Experience the romantic charm of Venice, the historic allure of Dubrovnik, and the stunning beauty of Sicily. Discover unspoiled beaches, medieval towns, and cultural treasures across Croatia, Montenegro, and Italy.
Cruise Details
0
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