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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 24 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
SS 25%
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
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
Enjoy stunning views from the island of Santorini
from $2,500
Air Credit
EXPLORE

Eternal Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
  • Explore Athens ancient Agora
  • Discover Milos volcanic landscapes
  • Visit Adamas Sarakiniko Bay
  • Enjoy Santorini black sand beaches
Starts / Ends
Piraeus / Piraeus
Activities
Archaeological Site Visits, Small Ship Sailing, Village Visits, Local Market Visits
Activity Level
Variable
Embark on an 8-day cruise aboard the Star Flyer, exploring ancient sites in Greece and Turkey, including the Acropolis and the ruins of Halicarnassus. Visit beautiful destinations like Milos, Crete, Santorini, and Hydra before concluding your journey in 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
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
SS 25%
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
Volcanic landscape on Milos, Greek Islands, with clear water
from $7,495
EXPLORE

Summer Breeze Through The Aegean

Athens to Athens - 8 Day Itinerary aboard Sea Cloud II
  • Uncover the secrets of the Cyclades
  • Explore Epidaurus’ living history
  • See Panagia Hozoviotissa
  • Stroll charming Aegean harbor town
Starts / Ends
Piraeus / Athens
Activity Level
Variable
Experience an 8-day Mediterranean cruise aboard Sea Cloud II roundtrip from Athens. Sail the Aegean Sea under full canvas, explore Amorgos and Milos in the Cyclades, visit Nauplio and Poros in the Peloponnese, and discover UNESCO World Heritage sites including Epidaurus and the Acropolis.
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
SS 25%
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
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Franny F.
Stop in Piraeus, the port of Athens
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