Piraeus Sailing Cruises

from $2,410

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Southern Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer

• Explore Piraeus vibrant port city
• Wander Rhodes medieval streets
• Discover Bodrum rich history
• Admire Santorini whitewashed cliffs

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

Set sail for 8 days on the Star Flyer, exploring historic Aegean ports from Piraeus to Rhodes and Bodrum while enjoying stunning views in Santorini and Hydra. Experience local culture, cuisine, and relaxation, culminating in a memorable return to Piraeus.

Cruise Details

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from $2,410

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Northern Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer

• Explore Piraeus bustling port city
• Discover Kusadasi grand ruins
• Visit Amorgos soaring cliffs
• Stroll Mykonos harbor

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

Set sail on an 8-day cruise aboard the Star Flyer to explore Greece’s ancient ruins and beautiful islands, starting in Piraeus. Experience vibrant destinations like Kusadasi, Patmos, and Mykonos while enjoying guided tours and hands-on sailing activities.

Cruise Details

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from $12,709

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Sailing the Greek Isles

8 Day Itinerary aboard Sea Cloud

• Experience the Cyclades
• Discover the ruins of Delos
• Discover the age-old villages
• Discover the beauty of Santorini

Starts / Ends

Athens / Athens

Activity Level

Variable

Explore the sun-kissed Greek Isles on this 8 luxury cruise aboard the Sea Cloud, a 58-guest sailboat. Each stop on this round trip cruise from Piraeus is brimming with activities, such as exploring the sanctuary ruins of Delos, the iconic cliffside villages of Santorini, and the Classical Greek culture and mythology.

Cruise Details

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from $3,970

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Grand Voyage: Athens to Athens

Roundtrip Piraeus - 15 Day Itinerary aboard Star Clipper

• Walk in the shadow of the Acropolis
• Explore Dikili’s and nearby Bergama
• Discover Myrina’s Kastro
• Shop in Skiathos markets

Starts / Ends

Piraeus / Piraeus

Activities

Snorkeling

Activity Level

Variable

Embark on a 15-day cruise aboard the Star Clipper, sailing through Greece and Turkey, from the Acropolis of Pergamon to the vibrant shores of Mykonos. Discover breathtaking landscapes, ancient ruins, and rich culture while enjoying adventure and relaxation at sea.

Cruise Details

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from $2,410

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Sporades Highlights

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer

• Explore Athens' Acropolis
• Discover Pergamon’s acropolis
• Stroll Skopelos whitewashed streets
• Admire Poros’ naval traditions

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

Set sail on an 8-day cruise aboard the Star Flyer, exploring Greece and Turkey's rich history and stunning landscapes. Enjoy traditional tall-ship sailing and breathtaking Aegean destinations from ancient Athens to charming Skopelos.

Cruise Details

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from $2,590

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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

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from $15,796

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Under Sail: Greece and the Dalmatian Coast

11 Day Itinerary aboard Sea Cloud

• Sail a tall ship in historic waters
• Tour ruins in Greece and Albania
• Skim Montenegro’s Gulf of Kotor
• Spend a day in Dubrovnik's Old Town

Activity Level

Variable

Spend 11 days immersed in the history & culture of the Mediterranean as you cruise aboard the Sea Cloud. Experience the crystal blue waters of the Aegean, Ionian, and Adriatic Seas as you visit Greece, Albania, Montenegro, and Croatia, home to historic sites and surprising beauty, like hiking or strolling in Dubrovnik, Ithaca, Korcula, and Hvar.

Cruise Details

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from $3,610

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Greece, Montenegro & Croatia

Athens - Venice - 12 Day Itinerary aboard Star Clipper

• View beautiful Mykonos
• Walk through sacred temples
• Discover historic Dubrovnik
• Explore the lovely Cres Town
• Visit inviting Korcula

Starts / Ends

Piraeus / Venice

Activity Level

Variable

Join Star Clipper on this 12-day cruise from Athens to Venice. Relax on the teak decks of the majestic tall ship as it sails along the clear waters around Mykonos, Santorini, Katakolon, Corfu, Kotor, Dubrovnik, Korcula, Hvar, Cres, and Venice! Along the way, you can learn about the mythology born here and soak in the sun!

Cruise Details

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from $13,995

EBD

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Sailing the Greek Islands

Roundtrip Athens - 12 Day Itinerary aboard Douglas Mawson

• Wander Athens’ ancient sites
• Explore Mykonos’ vibrant culture
• Tour Ephesus’ ancient ruins
• Relax on Patmos beaches

Starts / Ends

Athens / Piraeus

Activities

Local Market Visits

Activity Level

Variable

Set sail on a 12-day cruise aboard the Douglas Mawson through Greece's stunning islands, experiencing vibrant villages and rich Mediterranean culture. Discover historical gems like Rhodes, Santorini, and Ephesus while starting your adventure in Athens.

Cruise Details

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from $4,140

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Grand Voyage: Athens to Athens

Roundtrip Piraeus - 15 Day Itinerary aboard Star Flyer

• Discover Mykonos’ harbor
• Wander Dikili’s streets
• Marvel at Istanbul’s skyline
• Unwind in Skopelos sandy coves

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

Set sail on a 15-day cruise aboard the Star Flyer, exploring Greece and Turkey’s historic ports. Experience Athens, Mykonos, Istanbul, and picturesque islands while enjoying hands-on sailing and breathtaking coastlines.

Cruise Details

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from $3,450

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Greece, Montenegro & Croatia

Piraeus - Venice - 12 Day Itinerary aboard Star Flyer

• Discover Mykonos
• Experience Santorini
• Explore Corfu
• Discover Kotor

Starts / Ends

Piraeus / Venice

Activity Level

Variable

Embark on a 12-day cruise aboard the Star Flyer. Discover ancient Athens, the charm of Mykonos, the beauty of Santorini, the sacred sites of Katakolon, Corfu's lush landscapes, the medieval allure of Kotor, Dubrovnik's splendor, Korcula's history, Hvar's lavender fields, and the romance of Venice.

Cruise Details

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from $11,795

EBD

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Greece & Turkey: Turkish Delight

Roundtrip Athens - 13 Day Itinerary aboard Douglas Mawson

• Explore Athens’ iconic Acropolis
• Wander Chios’ mastic villages
• Discover Anavatos ghost village
• Experience Istanbul’s Grand Bazaar

Starts / Ends

Athens / Athens

Activities

Wine Tasting, Cooking Classes

Activity Level

Variable

Set sail on a 13-day cruise aboard the Douglas Mawson to explore Turkey and the Greek islands. Experience vibrant Istanbul, the ruins of Ephesus, the beauty of Bodrum, and honor the sacrifices at Gallipoli, all while journeying through powerful historical narratives.

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 $3,610

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Greece, Montenegro and Croatia

Venice - Piraeus - 12 Day Itinerary aboard Star Clipper

• Explore Venice’s canals
• Relax on Mali Losinj’s beaches
• Stroll Gythio’s harbor
• Admire Milos’ white cliffs

Starts / Ends

Venice / Piraeus

Activity Level

Variable

Set sail on a 12-day cruise from Venice to Piraeus on the Star Clipper, exploring Croatia, Montenegro, and Greece. Experience stunning destinations like Dubrovnik, Kotor, and Mykonos while enjoying leisure activities.

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 $3,450

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Greece, Montenegro & Croatia

Venice - Athens - 12 Day Itinerary aboard Star Flyer

• Admire Venice’s romantic icons
• Explore Cres' Venetian charm
• Wander Hvar amid lavender fields
• Stroll Corfu’s lush hillsides

Starts / Ends

Venice / Piraeus

Activity Level

Variable

Set sail on a 12-day cruise from Venice to Piraeus aboard the Star Flyer, visiting stunning Mediterranean ports like Dubrovnik, Kotor, and Santorini. Enjoy onboard activities and guided excursions highlighting local culture and history across Italy, Croatia, Montenegro, and Greece.

Cruise Details

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from $2,410

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Yachtsman's Paradise

Istanbul - Piraeus - 8 Day Itinerary aboard Star Flyer

• Explore Istanbul’s dynamic blend
• Visit Dikili’s quiet harbor
• Wander Skopelos Town’s alleys
• Walk Piraeus to ancient Athens

Starts / Ends

Istanbul / Piraeus

Activities

Small Ship Sailing, Archaeological Site Visits, Village Visits

Activity Level

Variable

Embark on an 8-day cruise from Istanbul to Athens aboard the Star Flyer, exploring ancient sites like Pergamon and experiencing charming coastal towns. Conclude your journey in historic Athens, the cradle of democracy and Western philosophy.

Cruise Details

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from $2,300

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Southern Cyclades

8 Day Itinerary aboard Star Clipper

• Explore beautiful Rhodes
• Visit Halicarnassus
• Discover breathtaking Santorini
• Ride a donkey to a lookout point

Starts / Ends

Piraeus / Piraeus

Activity Level

Variable

On this 8-day cruise through the Mediterranean on the Star Clipper, you can enjoy the traditional charm of the Southern Cyclades Islands. Discover the magic and mythology of the Greek Isles as you visit the small port towns of Rhodes and Hydra and the legendary island of Santorini. Visit sun-kissed beaches, ancient ruins, and modern cities along the way.

Cruise Details

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