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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 2026. 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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    • Santorini
Traditional architecture in Greece.
from $2,871
EBD 10%
EXPLORE

Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Galileo
  • Capture Santorini’s caldera views
  • Swim Poliegos turquoise waters
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
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.
Cruise Details
0
Walking in Santorini
from $2,410
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
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
Village Visits, Archaeological Site Visits, Small Ship Sailing, 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
from $3,090
Up to 50%
EXPLORE

Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Panorama
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
  • Swim Poliegos turquoise waters
  • Explore Poros neoclassical charm
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.
Cruise Details
0
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Greece

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TrustScore 4.9 | 1045 reviews
TrustScore 4.9 of 5
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Based on 1045 reviews on
review score
1 week ago
Quick response and very helpful. Answered my questions and adjusted the trip
Andrew Smith
review score
2 months ago
The website was easy to navigate, and my trip planner was helpful, available, and creative. I was able to customize my trip as needed.
Wanderwegger
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3 months ago
We loved the experience on Atlas. It was 5 star in every way. Best food I have had in my life
customer
review score
6 months ago
Kassandra is prompt, knowledgeable, helpful, and generally lovely to work with. Makes the trip all the more exciting to look forward to when you feel you are in trusted hands. Not my first time using Adventure Life, and certainly not my last!
Kyla
review score
7 months ago
Quick response and efficient team work
L.Davidson

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