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Explore the stunning island of 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, Small Ship Sailing, Hiking, and Scuba Diving. Prices for trips in May 2026 range from $3,090 to $19,400 for a vacation of 8 to 12 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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    • Santorini
Explore the beautiful walkways of Santorini
from $4,188
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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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Traditional architecture in Greece.
from $3,090
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
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See the ancient world come alive in Athens
from $3,350
EBD
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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
Wander through the maze of colorful buildings on Santorini
from $5,390
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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
Visit charming Naxos
from $3,400
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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
Old town harbor of Antalya
from $10,300
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Athens (Piraeus) to Split

12 Day Itinerary aboard Silver Dawn
  • Explore ancient Athens landmarks
  • Visit Hadrian’s Roman gate
  • Discover Rhodes medieval history
  • Tour Butrint’s ancient ruins
Starts / Ends
Athens / Split
Activities
Small Ship Sailing, Archaeological Site Visits, Village Visits, Spa Relaxation
Activity Level
Variable
Sail through the Mediterranean on a 12-day cruise from Athens to Split aboard the Silver Dawn. Stroll through Rhodes’ medieval streets, discover Crete’s legendary lakeside charm, and soak in Santorini’s volcanic beauty and caldera views. In Albania, visit Sarande’s Blue Eye Spring and the ancient ruins of Butrint.
Cruise Details
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