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Oia, Santorini

Milos Small Ship Cruises

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Experience the charm of authentic Greece on the enchanting islands this year with Adventure Life's selection of 15 small ship cruises. Delve into the serene tranquility of the Greek island kingdoms aboard various vessels, such as the Sea Cloud II. Explore the uncharted Cyclades islands, steep cliffs, enchanting monasteries, and the mysteries they hold. Embrace the rich history and culture of the Aegean Sea on cruises that visit UNESCO World Heritage Sites, ancient ruins, and mythical birthplaces. Swim in the crystal-clear waters of Milos beaches, taste exquisite wines in Santorini, and wander through vineyard terraces. Discover the hidden pearls of the Aegean Sea, avoid tourist crowds, and revel in the beauty of the Isle of Light and its temples. Whether you're seeking archaeological site visits, village exploration, or wine tasting experiences, these cruises offer a relaxed pace suitable for all travelers. Don't miss the chance to embark on an unforgettable journey through the wonders of Greece. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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Hiking in the Cyclades
from $7,735
No SS
EXPLORE

Greek Isles Odyssey: Mythology, History and Cerulean Seas

Athens to Athens - 8 Day Itinerary aboard National Geographic Orion
  • Explore Milos Kleftiko sea caves
  • Visit Paros villages
  • See Naxos olive press museum
  • Visit Tinos Pyrgos artisan village
Starts / Ends
Athens / Athens
Activities
Cooking Classes, Kayaking
Activity Level
Variable
Start in Athens and board National Geographic Orion in Lavrio to explore the Cyclades on this 8-day cruise. Visit Milos sea caves, walk Sifnos villages, kayak in Serifos, taste wine in Paros, explore Naxos farms, and discover Delos ruins and Tinos artisan towns before returning to Athens.
Cruise Details
0
The famous windmills of Mykonos
from $5,405
15% OFF
EXPLORE

Sparkling Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
  • See pristine waters of Milos
  • Explore Sifnos' vibrant culture
  • Enjoy swimming in Despotiko
  • Visit ancient ruins in Delos
Starts / Ends
Lavrion / Lavrion
Activity Level
Variable
Embark on an 8-day cruise through the stunning Cyclades on the Gemaya, exploring charming islands like Milos, Sifnos, and Delos, rich in culture and natural beauty. Experience pristine beaches, delightful hiking, and vibrant local cuisine before concluding your adventure in Lavrion.
Cruise Details
0
Mykonos at Dusk
from $11,990
EXPLORE

Athens to Istanbul Adventure

Athens (Piraeus) - Istanbul - 8 Day Itinerary aboard Emerald Azzurra
  • Discover Santorini cliff villages
  • Tour Delos archaeological ruins
  • Visit Ephesus near Kusadasi
  • End journey in Istanbul
Starts / Ends
Athens / Istanbul
Activity Level
Variable
Explore Greece and Turkey on an 8-day cruise aboard Emerald Azzurra. Discover Santorini’s iconic cliffside villages, ancient ruins in Delos and Ephesus, sacred sites in Patmos, and the historic coastlines of Mykonos, Kusadasi, and Kepez. End the journey in Istanbul.
Cruise Details
0
Discover beautiful Symi island
from $6,870
EXPLORE

Greek Islands of the Southern Aegean – with Smithsonian Journeys

Athens Roundtrip - 8 Day Itinerary aboard Le Dumont-d'Urville
  • Explore Athens Acropolis landmarks
  • Visit Patmos monastery heritage
  • Discover colorful Symi harbor
  • Discover lively Mykonos streets
Starts / Ends
Athens / Hermes Hotel - Athens
Activities
Archaeological Site Visits, Village Visits
Activity Level
Variable
Discover Greece on an 8-day voyage aboard Le Dumont-d'Urville, visiting Athens, Patmos, Symi, Amorgos, Milos, Delos, Mykonos, and Nafplion. Explore UNESCO World Heritage sites, charming villages, volcanic coastlines, and crystal-clear coves. Sail through the Santorini Caldera, walk historic streets, and experience authentic Greek island culture.
Cruise Details
0
Enjoy stunning views from the island of Santorini
from $2,500
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
Small Ship Sailing
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
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
Discover beautiful Symi island
from $9,499
Air Credit
EXPLORE

Greece And Turkish Isles

Athens Roundtrip - 12 Day Itinerary aboard World Traveller
  • Explore Hydra coastal path
  • Amorgos cliff monastery visit
  • Explore Kusadasi and Ephesus ruins
  • Explore Rhodes Old Town
Starts / Ends
Piraeus / Piraeus
Activities
Hiking, Wine Tasting
Activity Level
Variable
Explore Greece on a 12-day voyage aboard World Traveller, across Athens, Milos, Crete, Rhodes, Amorgos, Folegandros, and Hydra, with visits to Bodrum and Kusadasi in Turkey. Experience local markets, coastal views, and cultural landmarks. This voyage stands out for combining iconic Greek islands with ancient Turkish heritage sites in one journey.
Cruise Details
0
Visit charming Naxos
from $3,355
EXPLORE

Divine Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Discover Ios golden beach
  • Swim Naxos crystal waters
  • Wander Mykonos vibrant alleys
  • Explore Delos sacred ruins
Starts / Ends
Lavrion / Lavrion
Activity Level
Variable
Embark on an 8-day cruise aboard the Elysium through the enchanting Cyclades. Discover this enchanting paradise, holding ancient secrets, and embark on a journey to explore its beauty.
Cruise Details
0
Admire the ruins of a temple on Naxos
from $2,000
Spcl Rates
EXPLORE

Greek Easter Vibes

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Explore Delos sacred wonders
  • Witness Santorini stunning sunset
  • Swim Naxos crystal-clear waters
  • Celebrate Mykonos festive Easter
Starts / Ends
Lavrion / Lavrion
Activity Level
Variable
Experience Greek Easter on an 8-day cruise aboard the Elysium, visiting 10 Aegean islands like Mykonos and Santorini. Enjoy stunning sites, traditional festivities, and finish with a swim at Cape Sounion's Temple of Poseidon before returning to Athens.
Cruise Details
0
Enjoy the natural beauty of Rhodes
from $6,999
Air Credit
EXPLORE

Aegean Tastes And Tales

Athens Roundtrip - 9 Day Itinerary aboard World Traveller
  • See Hydra harbor village views
  • Mykonos windmills scenic stroll
  • Explore Rhodes medieval town
  • See Agios Nikolaos harbor views
Starts / Ends
Piraeus / Piraeus
Activity Level
Variable
Sail through the Aegean and explore iconic destinations across Greece and Turkey on a 9-day cruise aboard World Traveller. Discover ancient ruins, coastal villages, and island culture. Walk through historic streets, relax on beaches, and explore archaeological landmarks
Cruise Details
0
Stroll the ancient walkways of Athens
from $5,999
Air Credit
EXPLORE

Ancient Mosaics

Athens to Naples - 9 Day Itinerary aboard World Traveller
  • Milos Sarakiniko beach views
  • Explore Ephesus ancient ruins
  • Capri Blue Grotto visit
  • Ionian Sea scenic cruising
Starts / Ends
Piraeus / Naples
Activity Level
Variable
Sail through Greece, Turkey, and Italy starting in Athens on a 9-day cruise aboard World Traveller. Discover historic landmarks, seaside villages, and local cuisine. Enjoy shore excursions, cultural sites, and coastal scenery that define this Mediterranean adventure.
Cruise Details
0
Admire the ruins of a temple on Naxos
from $17,395
EXPLORE

Ancient Empires: Athens to Istanbul

Athens - Istanbul - 12 Day Itinerary aboard Scenic Ikon
  • Explore Athens ancient Parthenon
  • Wander Hydra whitewashed homes
  • Discover Milos rock formations
  • Visit Heraklion Palace of Knossos
Starts / Ends
Piraeus / Istanbul
Activities
Local Market Visits, Urban Exploration
Activity Level
Variable
Join a 12-day Eastern Mediterranean cruise from the Greek islands to Istanbul on the Scenic Ikon, exploring ancient sites like Ephesus and the charm of Santorini and Hydra. Enjoy guided excursions that highlight regional traditions, historical landmarks, and delicious Mediterranean cuisine.
Cruise Details
0
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Jess H.
Oia, Santorini
Greece

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