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Explore the stunning island of Santorini

Santorini Sailing Cruises

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Experience the magic of Greece's Santorini with Adventure Life's selection of small ship sailing Cruises for 2025. Discover the stunning Southern Cyclades, from the historical gems of Rhodes to the breathtaking vistas of Santorini, where you can even ride a donkey to a lookout point. Join us on an 8-day adventure exploring unique island cultures, ancient treasures, and pristine beaches aboard the Star Flyer or Star Clipper. Whether you're into archaeological site visits, small ship cruising, or simply soaking in the relaxed pace of the journey, this trip offers something for everyone. Don't miss the chance to sail through this Mediterranean paradise and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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Walking in Santorini
from $2,410
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Southern Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
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.
  • Explore Piraeus vibrant port city
  • Wander Rhodes medieval streets
  • Discover Bodrum rich history
  • Admire Santorini whitewashed cliffs
Cruise Details
0
Church in the center of Marpissa, Paros, Greece
from $2,500
EBD 10%
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Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Galileo
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on an 8-day cruise aboard the Galileo, exploring the beautiful Cyclades from Athens to islands like Santorini, Mykonos, and Folegandros. Enjoy swim stops, cultural experiences, and delightful Cycladic cuisine on this unforgettable journey.
  • Capture Santorini’s caldera views
  • Swim Poliegos turquoise waters
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
Cruise Details
0
Adventures in Santorini!
from $12,709
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Sailing the Greek Isles

8 Day Itinerary aboard Sea Cloud
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.
  • Experience the Cyclades
  • Discover the ruins of Delos
  • Discover the age-old villages
  • Discover the beauty of Santorini
Cruise Details
0
St.Blaise Church, Dubrovnik
from $3,610
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Greece, Montenegro & Croatia

Athens - Venice - 12 Day Itinerary aboard Star Clipper
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!
  • View beautiful Mykonos
  • Walk through sacred temples
  • Discover historic Dubrovnik
  • Explore the lovely Cres Town
  • Visit inviting Korcula
Cruise Details
0
Turquoise sea of Hvar island
from $3,450
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Greece, Montenegro & Croatia

Venice to Athens - 12 Day Itinerary aboard Star Flyer
Starts / Ends
Venice / Piraeus
Activity Level
Variable
Discover the hidden gems of the Dalmatian Coast and the spectacular views of the famous Greek Islands on this 12-day cruise aboard the Star Flyer. Visit Cres, Hvar, Kotor, Santorini, Mykonos, and more as you relax on the teak decks of your luxurious tall ship!
  • Glide in a gondola in Venice
  • Visit Lubenice, a UNESCO site
  • Admire Hvar's beauty
  • Explore cosmopolitan Mykonos
Cruise Details
0
Donkeys are a traditional form of transportation in Greece
from $3,450
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Greece, Montenegro & Croatia

Piraeus - Venice - 12 Day Itinerary aboard Star Flyer
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.
  • Discover Mykonos
  • Experience Santorini
  • Explore Corfu
  • Discover Kotor
Cruise Details
0
The famous windmills of Mykonos
from $13,995
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Sailing the Greek Islands

Roundtrip Athens - 12 Day Itinerary aboard Douglas Mawson
Starts / Ends
Athens / Piraeus
Activities
Small Ship Sailing, Archaeological Site Visits, Village Visits, Local Market Visits, 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.
  • Wander Athens’ ancient sites
  • Explore Mykonos’ vibrant culture
  • Tour Ephesus’ ancient ruins
  • Relax on Patmos beaches
Cruise Details
0
from $2,500
2for1
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Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Panorama
Activity Level
Variable
Set sail on an 8-day cruise aboard the Panorama, exploring the beautiful Cyclades from Athens to islands like Santorini, Mykonos, and Folegandros. Enjoy swim stops, cultural experiences, and delightful Cycladic cuisine on this unforgettable journey.
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
  • Swim Poliegos turquoise waters
  • Explore Poros neoclassical charm
Cruise Details
0
Walking in Santorini
from $2,300
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Southern Cyclades

8 Day Itinerary aboard Star Clipper
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.
  • Explore beautiful Rhodes
  • Visit Halicarnassus
  • Discover breathtaking Santorini
  • Ride a donkey to a lookout point
Cruise Details
0
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