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Adventures in Santorini!

Top Santorini Trips & Tours in May 2026

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Discover Santorini in May 2026 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Archaeological Site Visits, Village Visits, Hiking, Scuba Diving, and Small Ship Sailing. Prices for trips in May 2026 range from $3,090 to $7,675 for a vacation of 8 to 9 days. Choose any of the below 6 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Santorini trip planners.
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Traditional architecture in Greece.
from $3,090
Up to 30%
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
Activities
Small Ship Sailing
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
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Explore the beautiful walkways of Santorini
from $4,175
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Greece Island Hopping

9 Day Itinerary
  • Visit Athens, the capital of Greece
  • See iconic landmark in Athens
  • Visit the charming town of Naoussa
  • Relax in Paros' beautiful beaches
  • Capture the famous Santorini sunset
  • Sample local wines in Santorini
  • Enjoy the beauty of Santorini
Starts / Ends
Athens / Athens
Activities
Wine Tasting
Activity Level
Relaxed
Embark on an unforgettable 9-day Greece island-hopping adventure, exploring the stunning islands of Athens, Paros, and Santorini. This journey will take you through a perfect blend of ancient history and breathtaking landscapes. Be ready for a trip filled with azure waters, sun-drenched beaches, delicious cuisine, and picturesque villages.
Tour Details
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See the ancient world come alive in Athens
from $3,350
Up to 30%
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Classical Greece

Roundtrip Athens - 8 Day Itinerary aboard Harmony G
  • Explore Kea’s charming port
  • Discover Delos archaeological site
  • Visit Monemvasia’s medieval streets
  • Stroll Nafplion’s old town
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on an 8-day cruise from Athens aboard the Harmony G, exploring the Cyclades, Crete, and the hidden gem of Kythira. Discover historic charm in Monemvasia and Nafplion while enjoying a unique blend of cruising and yachting.
Cruise Details
0
Visit charming Naxos
from $3,385
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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
Activities
Hiking
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
Wander through the maze of colorful buildings on Santorini
from $5,405
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Aegean Escape

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
  • Explore Sifnos scenic trails
  • Discover Sikinos landscapes
  • Relax on Ios with pristine beaches
  • Visit Serifos with rugged landscape
Starts / Ends
Lavrion / Lavrion
Activities
Scuba Diving
Activity Level
Variable
Set sail on an 8-day cruise to the Aegean aboard the Gemaya, exploring stunning islands like Santorini and Milos. Discover whitewashed villages, hidden coves, and the rich traditions of Greece amidst a backdrop of beauty and myth.
Cruise Details
0
from $3,090
Up to 30%
EXPLORE

Αegean Food & Culture Stories

Roundtrip Piraeus - 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
Activities
Village Visits, Archaeological Site Visits
Activity Level
Variable
Join an 8-day culinary cruise in the Cyclades on the Galileo, hosted by culinary expert Angelis Nannos. Experience daily tastings, learn about Aegean traditions, and explore beautiful islands while enjoying insights into the region's food and agriculture.
Cruise Details
0
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