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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 11 Sicily sailing cruises in 2024. 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
$3,130
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
$3,130
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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Scenic view of Dubrovnik
$18,602
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
$2,830
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
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Beautiful Amalfi Coast
$2,080
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
Join an 8-day trip onboard Royal Clipper to experience the stunning Amalfi Coast and the amazing Italian Rivera, seeing Idyllic islands, charming cobbled villages, spectacular scenery, and intriguing history... capture the heart of the Mediterranean in a single cruise voyage. Each small harbor is …
Cruise Details
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Cruise into charming Sicily
$2,190
EXPLORE

Amalfi & Sicily

Civitavecchia Round-trip - 8 Day Itinerary aboard Royal Clipper
  • Gaze upon the Sistine Chapel
  • Snorkel at Palmarola
  • Visit historical Pompeii
  • Wander through the grand Duomo
Starts / Ends:
Civitavecchia / Civitavecchia
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Embark on an 8-day cruise aboard Royal Clipper through Amalfi and Sicily! Explore Rome's iconic landmarks like St. Peter's and the Colosseum before hitting Sorrento's stunning coast. Dive into history at Pompeii and relish Amalfi's medieval charm, from its Duomo to the picturesque …
Cruise Details
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Hydra Island, Greece
$2,170
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
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Stop in Piraeus, the port of Athens
$1,660
EXPLORE

Sicily & Greece

Malta - Greece - 7 Day Itinerary aboard Star Clipper
  • Visit Sicily's archaeological sites
  • Explore historic Pilos
  • Roam Agora in Athens
  • Learn about Malta's history
Starts / Ends:
Valletta / Piraeus
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Embark on a 7-day cruise aboard Star Clipper and discover the fascinating history of Mediterranean gems. Begin in Valletta, the capital of Malta, boasting museums and grand churches amidst its ancient walls. Next, explore Syracuse, a city in Sicily with remarkable ruins and charming cafes. Sail on …
Cruise Details
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The city of Bonifacio is built on stunning seaside cliffs along the riviera
$3,570
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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Wander through Rome
$3,570
EXPLORE

Grand Voyage: Venice to Rome

15 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
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
On this 15-day Grand Voyage cruise from Venice to Rome aboard Royal Clipper, visit Venice's iconic landmarks, such as San Marco, the Bridge of Sighs, Doge's Palace, La Fenice Opera House, the Church of San Giorgio Maggiore, and the Grand Canal before exploring Rovinj's Baroque …
Cruise Details
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View of Valletta
$4,060
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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