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Coast of Ortigia island at city of Syracuse

Sicily & Greece

Piraeus - Valletta - Example 9 Day Cruise aboard Star Clipper
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Embark on a 9-day cruise aboard the Star Clipper. This Mediterranean cruise explores Greece, Sicily, and Malta, blending ancient history, stunning landscapes, and cultural experiences. Begin in Athens, the birthplace of democracy, before sailing to Nafplio’s Venetian charm and Monemvasia’s medieval fortress. Discover Pilos’ historic bay and enjoy a day at sea aboard a majestic tall ship. Arrive in Sicily, where Taormina’s coastal beauty and Syracuse’s ancient ruins await. Explore Gozo, Malta’s serene island known for diving and mythology, before concluding in Valletta, a UNESCO-listed capital rich in history. This itinerary offers a seamless mix of discovery, relaxation, and adventure.
Athens AcropolisView of VallettaExplore beautiful Nafplion, GreeceExplore ruins in Taormina within view of volcanic Mount EtnaCoast of Ortigia island at city of Syracuse
Highlights
  • Explore Piraeus, Greece’s historic and bustling port city
  • Wander Nafplio, a charming town with Venetian elegance
  • Discover Monemvasia, a medieval fortress town by the sea
  • Visit Syracuse, an ancient Sicilian city with ruins
Activity Level: Variable
Activity options vary depending on destination and operator. Activity level is determined by the range and intensity of activities you choose to participate in. Discuss with your Trip Planner which options are best for you.
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Full Itinerary

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Day 1: Piraeus, Greece | Embark

Strolling through the Agora beneath the Acropolis, you can almost hear Plato, Socrates, and Aristotle debating their philosophical legacies. As the birthplace of democracy and the heart of Western civilization, ancient Athens remains timeless. Its port, Piraeus, lies just 15 km from the city center and 45 km from the airport.

Day 2: Nafplio, Greece

Nafplio, a picturesque seaport in the Peloponnese, is among Greece’s most romantic towns. Elegant Venetian houses, neoclassical mansions, and fascinating museums sit beneath the imposing Palamidi Fortress. Quayside cafés offer a perfect spot to unwind, while charming boutiques cater to avid shoppers. An excellent base for exploring nearby ancient sites, Nafplio is a favorite getaway for Athenians, making it especially lively during peak season.

Day 3: Monemvasia, Greece

It's a big rock sticking out into the sea from the shore. Then you pass over the causeway and through an iron fortress gate, and suddenly, the town of Monemvasia is before you, a perfectly preserved Byzantine fortified port, once 60,000 strong, now home to just a few hundred. You can readily see why the name Monemvasia means single entrance! In the rocky hills above, ancient Byzantine ruins loom over the town, while below, a maze of red-tiled roofs and twisting alleys hide tavernas and cafes and the home of revered Greek poet Yannis Ritsos.

Day 4: Pilos, Greece

Homer's 'Wise King Nestor' was wise to build his magnificent palace near Pilos. The city's harbor of Navarino Bay and the land-locked lake that was the original harbor was a perfect refuge from storms - and invaders. At this site, on October 20, 1827, with the help of Britain, Russia, and France, modern Greece attained independence, defeating the Turkish navy in the Battle of Navarino Bay.

Day 5: At Sea

Each Star Clippers ship offers a traditional and elegant way to see the world. Feel the wind fill the sails and gently carry you from one gorgeous destination to the next. During your time on board, you can choose to relax on a sun lounger or cool off in one of the pools on the top deck, while more adventurous passengers may enjoy the opportunity to climb the rigging or even have a go at steering the ship. Alternatively, you can wander the interior areas of the ship and discover relaxing lounges and a peaceful library.

Day 6: Taormina, Sicily, Italy

Barreling under full sail through the narrow Strait of Messina past Scylla and Charybdis, where rock and whirlpool almost claimed Ulysses, you arrive in lovely Taormina. Perched on the shoulder of Mt. Etna, Taormina inspired Goethe to say, ' It is the greatest work of art and nature.'

Day 7: Syracuse, Sicily, Italy

Syracuse is a city on the Ionian coast of Sicily known for its ancient ruins. It was once the largest city in the world, bigger than Athens and Corinth and as you can imagine it's steeped in history. Visit Parco Archeologico della Neapolis, one of Sicily's greatest archaeological sites. Relax in one of its stylish little cafes surrounding its beautiful baroque piazzas before wandering down its medieval lanes towards the sparkling blue sea.

Day 8: Gozo, Malta

The charm of Malta's sister island, Gozo, is immediately apparent. Steeped in myth, Gozo is considered the legendary Calypso's isle of Homer's Odyssey. It's green, rural and calm relying on fishing and agriculture as well as tourism. It is one of the Mediterranean's top diving destinations, with an incredible range of shore and boat dives, including reefs, caves, and wrecks. There are also Knight's watchtowers, tiny chapels, and beautiful, peaceful beaches to explore.

Day 9: Valletta, Malta | Disembark

  • 1 Breakfast
Valletta is the tiny capital of the island of Malta. The walled city was established in the 1500s on a peninsula by the Knights of St. John, a Roman Catholic order. It has a rich historical past and is a European Art City and a World Heritage City. It has an abundance of museums, palaces, and grand churches to visit, but be sure not to miss out on exploring one of its beautiful gardens.

Ship/Hotel

Star Clipper

Star Flyer/Star Clipper library
Star Flyer/Star Clipper deck

Dates & Prices

My Preferred Start Date

  • Oct 18, 2025from $2,590
<Oct 2025>
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Per person starting at
$2,590
Star Flyer, Star Clipper Cabin Category 6
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Category 6
Located on the Commodore Deck, this inside cabin features upper/lower berths and a bathroom with shower.
Star Flyer, Star Clipper Cabin Category 5
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Category 5
Located on the Clipper & Commodore Decks, this inside/outside cabin features a raised double bed, two lower beds, or triple berths, and a marble-lined bathroom with shower.
Star Flyer, Star Clipper Cabin 4
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Category 4
Located on the Commodore Deck, this outside cabin features two lower beds, double bed, or triple berths, and a marble-lined bathroom with shower.
Star Flyer, Star Clipper Cabin Category 3
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Category 3
Located on the Clipper & Commodore Decks, this outside cabin features two lower beds, double bed, or triple berths, and a marble-lined bathroom with shower.
Star Flyer, Star Clipper Cabin Category 2
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Category 2
Located on the Clipper Deck, this large outside cabin features two lower beds, double bed, or triple berths, and a marble-lined bathroom with shower.
Star Flyer, Star Clipper Cabin Category 1
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Category 1
Located on the Main & Sun Decks, this deluxe deck cabin features two lower beds that can convert to a double bed, minibar, marble-lined bathroom with whirlpool bath, and cabin doors that open onto the deck.
Owner's Suite view
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Owner's Cabin (Double)
Located on the Clipper Deck, this deluxe outside cabin features a double bed, sitting area, minibar, and marble-lined bathroom with whirlpool.

Notes

Single supplement: A single supplement fare is available at 150% of the published cruise fare for categories 2-6 during the season in which passengers are traveling. It is available at 200% for category 1 cabins, Deluxe Suites, and Owner's Suites. Single space is capacity controlled.

Children's rate: Savings may be available for children under 18 years when traveling with a full-paying adult on select sailings and subject to availability. Contact us for details.
Included
  • 8 Breakfasts, 7 Lunches, 8 Dinners
  • 8 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Port Fees
  • All meals and snacks (open seating) including: Coffee and tea are available 24 hours a day. Different juices are included only for breakfast.
  • Ocean transportation to remote ports.
  • Complimentary snorkeling, kayaks, paddle boarding, water-skiing, windsurfing, and sunfish sailing (subject to weather conditions and local authorities).
Excluded
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Gratuities
  • Visa
  • All transfers to/from the boat from airports.
  • Laundry services 
  • Medical services
  • Shore Excursions
  • Alcoholic drinks and sodas.

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Everything was amazing! The planning with Adventure Life went smoothly. The actual trip was fantastic! One of the best trips I have experienced. The cruise staff members were knowledgeable and attentive. I will be writing more about this on the blog!
Justin Chappelle

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