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Sailing Trips in Sicily

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Balate Dorin
Visit charming Sicily
Civitavecchia
Aleksander Nalbantjan
Visit the Forum Romanum, the center of ancient Rome
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Choose from one of these 13 Sicily sailing cruises in 2022. Sailing with the sails full and the sun shining is an unforgettable experience that Adventure Life's Sicily sailing cruise experts can help you plan to perfection. Contact one of our Sicily sailing cruise experts for help planning your next trip.
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    • Sicily
Cape Drastis at Corfu island in Greece
$3,070
EXPLORE

Italy, Montenegro & Croatia

Venice to Rome - 12 Day Itinerary aboard Royal Clipper
  • Ride in a gondola in Venice
  • Visit the town of Rovinj
  • Call in at Kotor, Montenegro
  • Join an optional tour to Pompeii
Starts / Ends:
Venice / Civitavecchia
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Enjoy one of the most stunning destinations in Europe, the Eastern Mediterranean, aboard the luxury tall ship the Royal Clipper. Sail to Italy, Croatia, and Montenegro from Venice. Discover the heavenly scent of lavender in the fields and valleys around the island of Hvar. In Dubrovnik, the sense …
Cruise Details
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St.Blaise Church, Dubrovnik
$3,070
EXPLORE

Italy, Montenegro & Croatia

Rome to Venice - 12 Day Itinerary aboard Royal Clipper
  • Explore the Sistine Chapel
  • Snorkel at Palmarola
  • Visit the medieval city of Kotor
  • Cruise through Venice's canals
Starts / Ends:
Civitavecchia / Venice
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Sail aboard the tall ship Royal Clipper from Rome to Venice on this 12-day expedition. Fall asleep to the gentle rhythms of the ship and sea, and awake refreshed and ready to explore a new destination. Experience friendly and gracious service and a delightful menu of international foods from the …
Cruise Details
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Colosseum in Rome, Italy
$7,115
EXPLORE

Mediterranean: Civitavecchia to Valletta

9 Day Itinerary aboard Sea Cloud II
  • Admire beautiful Bonifacio
  • Walk around wonderful Naxos
  • Explore the Vatican State
  • Explore Capri and observe its charm
Starts / Ends:
Civitavecchia / Valletta
Activities:
Small Ship Sailing
Activity Level:
Relaxed
Explore the historical wonders of the Mediterranean on this 8-day small ship cruise sailing from Rome. Enjoy thepicturesque Amalfi Coast with its violet bougainvillea gracing pastel-pink facades, houses perched upon cliffs like swallows’ nests, and perron stairs with views out over the …
Cruise Details
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Scenic view of Dubrovnik
$16,950
EXPLORE

Mediterranean Gems: From Dubrovnik to Naples

Dubrovnik to Naples - 11 Day Itinerary aboard Sea Cloud
  • Explore Gerace
  • Tour the Amalfi Coast
  • Visit Pompeii
  • Explore Dubrovnik
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Relaxed
Marvel at ornate cathedrals and remarkable baroque buildings, explore great sites of antiquity—from renowned Pompeii to the less-visited Greek temples of Paestum—and meander through unspoiled clifftop towns, soaking up breathtaking views. Plus, with a little luck witness the orange glow …
Cruise Details
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Turquoise sea of Hvar island
$2,780
EXPLORE

Italy, Montenegro & Croatia

11 Day Itinerary aboard Royal Clipper
  • Ride in a gondola in Venice
  • Visit the town of Rovinj
  • Call in at Kotor, Montenegro
  • Join an optional tour to Pompeii
Starts / Ends:
Venice / Civitavecchia
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Sail to Italy, Croatia, and Montenegro from Venice. Discover the heavenly scent of lavender in the fields and valleys around the island of Hvar. In Dubrovnik, the sense of awe never fails to descend when you set eyes on the beauty of the old town. Barrel under full sail through the narrow Strait of …
Cruise Details
0
Visit the Cathedral of Palmero on your small ship cruise around Sicily
$2,040
EXPLORE

Amalfi & Sicily

Rome Roundtrip - 8 Day Itinerary aboard Royal Clipper
  • Gaze upon the Sistine Chapel
  • Visit a snorkeling heaven Palmarola
  • Join Pompeii's historical excursion
  • Wander through the grand Duomo
Starts / Ends:
Civitavecchia / Civitavecchia
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Idyllic islands, charming cobbled villages, spectacular scenery, intriguing history... capture the heart of the Mediterranean in a single cruise voyage. Each small harbor is especially suited for small ship exploration. Enjoy the best of the region — from the ancient ruins of Rome and …
Cruise Details
0
Visit the Cathedral of Palmero on your small ship cruise around Sicily
$6,195
EXPLORE

Sicily's Rich Cultural Heritage

Valletta to Syracuse - 8 Day Itinerary aboard Sea Cloud II
  • View the Cappella Palatina
  • Visit Syracuse, a UNESCO site
  • Take a cable car up Mt. Etna
  • Join a cooking class at Lipari
Starts / Ends:
Malta / Malta
Activities:
Archaeological Site Visits, Cooking Classes, Small Ship Sailing
Activity Level:
Relaxed
Be a part of this exclusive 8-day cruise and discover the most beautiful sights of Sicily, a magical place full of royal palaces, ancient temples, and heavenly panoramas. Delight yourself with the many facets of the largest Mediterranean island, a fabulously diverse microcosm in its own right with …
Cruise Details
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Sicilian landscape in the early evening
$1,850
EXPLORE

Amalfi & Sicily

Civitavecchia Roundtrip - 8 Day Itinerary aboard Star Clipper
  • Gaze upon the Sistine Chapel
  • Snorkel at Palmarola
  • Visit historical Pompeii
  • Wander through the grand Duomo
Starts / Ends:
Civitavecchia / Civitavecchia
Activities:
Small Ship Cruises, Small Ship Sailing, Urban Exploration, Village Visits
Activity Level:
Relaxed
Idyllic islands, charming cobbled villages, spectacular scenery, intriguing history... capture the heart of the Mediterranean in a single cruise voyage. Each small harbor is especially suited for small ship exploration. Enjoy the best of the region — from the ancient ruins of Rome and …
Cruise Details
0
The city of Bonifacio is built on stunning seaside cliffs along the riviera
$3,500
EXPLORE

Grand Voyage: Venice to Cannes

15 Day Itinerary aboard Royal Clipper
  • Explore traditional Rovinj
  • Swim in Dubrovnik's waters
  • Admire the scenery of Corfu
  • Sail through the Strait of Messina
Starts / Ends:
Venice / Cannes
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
This 15-day sailing expedition between Italy and France offers the flexibility to do as you wish with your days and evenings. Experience light-hearted fun, informal elegance, and no rigid schedules. Participate in classes such as knot tying and navigation, relax on the deck and watch as the sun …
Cruise Details
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View of Valletta
$3,970
EXPLORE

Grand Voyage: Athens to Malaga

19 Day Itinerary aboard Star Flyer
  • Admire romantic town Nafplio
  • Explore Syracuse's ancient ruins
  • Enjoy leisurely discovery
  • Visit Palma's Gothic cathedral
Starts / Ends:
Piraeus / Malaga
Activities:
Archaeological Site Visits, Local Market Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
From the stunning Balearic Islands to quixotic tiny port towns along the Italian Riviera, this 19-day sailing cruise takes you to an impressive collection of ports. Sailthrough an iron fortress gate to the town of Monemvasia, a perfectly preserved Byzantine fortified port with tons of history and …
Cruise Details
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View of Valletta
$3,030
EXPLORE

Grand Voyage: Malta to Istanbul

14 Day Itinerary aboard Star Flyer
  • Learn about Malta's history
  • Discover sites of ancient Greece
  • Visit cultural and historical sites
  • Relax aboard a majestic tall ship
Starts / Ends:
Valletta / Istanbul
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Join us for a delightful sailing experience and relax in some of the most historical and magical destinations in the Mediterranean. Start at the charming port of Valletta, Malta, featuring an abundance of museums, palaces, and grand churches to visit but be sure not to miss out on exploring one of …
Cruise Details
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Hydra Island, Greece
$2,090
EXPLORE

Sicily & Greece

Piraeus to Valletta - 9 Day Itinerary aboard Star Flyer
  • Ride a donkey on Hydra
  • Visit Sicily's archaeological sites
  • Explore historic Pilos
  • Discover Gozo, a diving destination
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Start your tall ship sailing expedition in the ancient city of Athens, the birthplace of democracy and epicenter of western civilization, a city for all eternity. Visit Syracuse, a city on the Ionian coast of Sicily that's known for its ancient ruins. It was once the largest city in the world, …
Cruise Details
0
Explore ruins in Sicily
$7,115
EXPLORE

On a Course of Longing through Bella Italia

Civitavecchia to Valletta - 9 Day Itinerary aboard Sea Cloud II
  • Explore the Vatican State
  • Admire beautiful Bonifacio
  • Discover Corsica's history
  • Visit the royal Capella Palatina
Starts / Ends:
Civitavecchia / Malta
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Explore the historical wonders of the Mediterranean on this 8-day small ship cruise sailing from Rome. Enjoy thepicturesque Corsica Coast with its houses perched upon cliffs like swallows’ nests, and perron stairs with views out over the turquoise sea. Discover Taormina, a stunning town in …
Cruise Details
0
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