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Stop in Piraeus, the port of Athens

Piraeus Sailing Cruises

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Experience the enchanting beauty and rich cultural tapestry of the Greek Isles with Adventure Life's array of 19 small ship sailing tours for 2026. Join us on a sailing journey through the Southern Cyclades, Montenegro, Croatia, and Sicily, discovering ancient treasures, breathtaking beaches, and historic sites. Whether you're exploring archaeological ruins, biking through charming towns, or visiting vibrant local markets, each moment offers a unique opportunity to immerse yourself in the wonders of this region. With activities like village visits, archaeological site exploration, and small ship cruises, this adventure offers a relaxed pace suitable for all travelers. Don't miss this opportunity to delve into the captivating nature, history, and culture of the Greek Isles. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Piraeus
Walking in Santorini
from $2,410
Air Credit
EXPLORE

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
0
The towering ruins of the Acropolis rise over Athens
from $2,410
Air Credit
EXPLORE

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
0
Sail the Mediterranean
from $2,500
Air Credit
EXPLORE

Greek Island Odyssey

Piraeus Roundtrip - 8 Day Itinerary aboard Star Flyer
  • Walk Ancient Athens landmarks
  • Explore Karpathos Harbor
  • Visit Ephesus Ruins
  • Explore Patmos Heritage
Starts / Ends
Athens / Piraeus
Activities
Village Visits
Activity Level
Variable
Sail for 8 days aboard Star Flyer on the Greek Island Odyssey through the Aegean Sea. Travel from Athens to Karpathos, Rhodes, Kusadasi, Patmos, and Andros, balancing iconic ports, historic sites, and relaxed sailing days before returning to Piraeus.
Cruise Details
0
Adventures in the Mediterranean
from $2,410
Air Credit
EXPLORE

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
0
Athens Acropolis
from $1,740
Air Credit
EXPLORE

Sicily & Greece

Piraeus - Valletta - 6 Day Itinerary aboard Star Clipper
  • Explore Athens ancient Agora
  • Walk Monemvasia twisting alleys
  • Wander Syracuse baroque piazzas
  • Discover Valletta capital
Starts / Ends
Piraeus / Valletta
Activities
Archaeological Site Visits, Small Ship Sailing
Activity Level
Variable
Embark on a 6-day Mediterranean cruise from Piraeus to Valletta aboard the Star Clipper, visiting historic sites in Greece, Italy, and Malta. Highlights include Monemvasia, Pilos, and Syracuse, concluding in Valletta, a UNESCO World Heritage site.
Cruise Details
0
The famous windmills of Mykonos
from $13,995
EBD
EXPLORE

Sailing the Greek Islands

Roundtrip Athens - 12 Day Itinerary aboard MV Douglas Mawson
  • Wander Athens’ ancient sites
  • Explore Mykonos’ vibrant culture
  • Tour Ephesus’ ancient ruins
  • Relax on Patmos beaches
Starts / Ends
Athens / Piraeus
Activities
Wine Tasting
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
0
Explore the ancient Acropolis
from $2,290
EXPLORE

Sicily & Greece

Piraeus - Valletta - 7 Day Itinerary aboard Royal Clipper
  • Wander Athens Ancient Agora
  • Explore Pylos Navarino Bay
  • Explore Syracuse’s historical ruins
  • Visit Valletta’s museums palaces
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Set sail on a 7-day Mediterranean cruise from Piraeus to Valletta aboard the Royal Clipper, exploring historic Athens, Monemvasia's Byzantine fortress, and Pylos, famous for King Nestor’s Palace. Discover Sicily's Syracuse and Malta's Gozo, known for diving and coastal caves, before concluding in the fortified capital of Valletta.
Cruise Details
0
Athens Acropolis
from $2,820
EXPLORE

Sicily & Greece

Piraeus - Valletta - 9 Day Itinerary aboard Star Flyer
  • Explore Milos Sarakiniko Bay
  • Visit Chania Venetian harbor
  • Walk Gythio streets
  • Explore Valletta the walled city
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Experience a 9-day Mediterranean sailing cruise on the Star Flyer, exploring ancient Athens, stunning Milos, and the charming alleys of Chania. Visit historic sites in Gythio, Pylos, Syracuse, Gozo, and end in Valletta, famous for its fortified city and gardens.
Cruise Details
0
A stunning view of Nafplion, Greece
from $2,150
EXPLORE

Sicily & Greece

Valletta to Athens - 7 Day Itinerary aboard Star Flyer
  • Explore Valletta the walled city
  • Explore Syracuse ruins
  • Visit Pilos Navarino Bay
  • Stroll Nafplio waterfront
Starts / Ends
Valletta / Piraeus
Activity Level
Variable
Join a 7-day cruise from Valletta to Piraeus on the Star Flyer, exploring historic sites like Syracuse's archaeological park and Monemvasia's Byzantine fortress. Visit Nafplio's Venetian architecture before concluding in Piraeus, where you can explore Athens' Acropolis and Agora.
Cruise Details
0
Historical Shipyard in Turkey
from $4,140
EXPLORE

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
0
Hagia Sophia in Istanbul
from $11,795
EBD
EXPLORE

Greece & Turkey: Turkish Delight

Roundtrip Athens - 13 Day Itinerary aboard MV Douglas Mawson
  • Explore Athens’ iconic Acropolis
  • Wander Chios’ mastic villages
  • Discover Anavatos ghost village
  • Experience Istanbul’s Grand Bazaar
Starts / Ends
Athens / Athens
Activities
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
0
Stone streets of Stari Grad on Hvar island
from $3,610
Air Credit
EXPLORE

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
0
Suez Canal Bridge, Egypt
from $3,240
EXPLORE

Suez Canal Crossing

Piraeus - Safaga - 11 Day Itinerary aboard Star Flyer
  • Walk Athens Agora historic site
  • Ride Hydra hills scenic trail
  • Explore Monemvasia fortress
  • Sail through Suez Canal
  • Explore Bodrum’s ruins
Starts / Ends
Piraeus / Safaga
Activities
Local Market Visits
Activity Level
Variable
Embark on an 11-day cruise aboard Star Flyer, exploring Greece and Egypt. Begin in Athens, visit Hydra, Monemvasia, Santorini, and Bodrum, and then continue to Rhodos, Alexandria, and Port Said. Explore ancient ruins, stunning islands, and vibrant cultures, with highlights including the Suez Canal and the Red Sea's crystal-clear waters.
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
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
Poros, Greece
from $2,410
Air Credit
EXPLORE

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
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
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
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
The pastel houses of Ponza Town
from $3,320
EXPLORE

Rome to Athens

Civitavecchia - Piraeus - 10 Day Itinerary aboard Royal Clipper
  • Watch Stromboli’s active volcano
  • Discover Crotone’s Greek heritage
  • Wander Parga’s cobbled lanes
  • Visit Katakolon
Starts / Ends
Civitavecchia / Piraeus
Activity Level
Variable
Set sail on a 10-day Mediterranean cruise from Civitavecchia to Piraeus aboard the Royal Clipper, visiting stunning locations like the Pontine Islands, Lipari, Taormina, and the historic sites of Ancient Olympia. The journey also includes Pargа, Monemvasia, and concludes in Piraeus, granting access to Athens.
Cruise Details
0
Cape Drastis at Corfu island in Greece
from $3,610
Air Credit
EXPLORE

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
0
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