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Explore the stunning island of Santorini

Top Santorini Trips & Tours in May 2025

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Discover Santorini in May 2025 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of Santorini, Athens, Mykonos, Delos, and Folegandros during May 2025 as you enjoy cruises, archaeological site visits, small ship cruises, beaches, and village visits. Prices for trips in May 2025 range from $2,030 to $16,930 for a vacation of 8 to 9 days. Choose any of the below 7 itineraries in May 2025 and customize it when you contact one of Adventure Life's expert Santorini trip planners.
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Explore the beautiful walkways of Santorini
$3,989
EXPLORE

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:
Archaeological Site Visits, Village Visits, Wine Tasting
Activity Level:
Relaxed
Escape to Greece on this 9-day Island Hopping Adventure that will take you to Athens, Paros, and Santorini. Start your journey in Athens, where you'll explore the architectural wonders of the ancient world, including the Acropolis and the Parthenon. Taste some of the finest Greek cuisines at …
Tour Details
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Church in the center of Marpissa, Paros, Greece
$2,500
EBD
EXPLORE

Jewels of the Cyclades

8 Day Itinerary aboard Galileo
  • Dine at traditional Greek Tavernas
  • Enjoy a swim-stop at Poliegos
  • Explore Delos's archaeological site
  • Walk through Syros
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Variable
Take an 8-day cruise on the Galileo, which leaves and returns to Athens, to see the Aegean Islands, known for their white-washed villages and ports, bright skies, and crystal seas. During your trip, you can visit popular destinations like Santorini and Mykonos, as well as lesser-known islands such …
Cruise Details
0
Wander through the maze of colorful buildings on Santorini
$4,915
EXPLORE

Aegean Escape

8 Day Itinerary aboard Gemaya
  • Visit Kythnos' famous baths
  • Explore the dreamy island of Sifnos
  • Explore Sarakiniko beach
  • Enjoy Santorini
  • See the sandy beaches of Magganari
Starts / Ends:
Lavrion / Lavrion
Activities:
Archaeological Site Visits, Kayaking, Local Market Visits, Small Ship Cruises, Snorkeling, Stand Up Paddle Boarding, Village Visits
Activity Level:
Variable
Explore the Aegean Sea's pristine Blue waters while cruising on the boutique yacht, Gemaya. This 8-day round-trip Greece cruise takes you around the Cyclades, to the famous Santorini and Milos islands, but most importantly, to lesser-known islands that are untouched, unspoiled, and …
Cruise Details
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The whitewashed cliffs of Santorini
$3,350
EBD
EXPLORE

Classical Greece

8 Day Itinerary aboard Harmony G
  • Explore the beautiful Cyclades
  • Visit the peaceful town of Chora
  • Tour the old quarter of Nafplion
  • Experience archaeological sites
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Snorkeling
Activity Level:
Variable
Board the Harmony G for a week-long round-trip cruise. On this 8-day cruise from and back to Athens, see Greece at its best: the beautiful white-washed Cycladic Islands of Santorini and Mykonos; Crete, the largest and southernmost Greek island; and the Peloponnese, with its historical treasures in …
Cruise Details
0
Milos
$2,850
EXPLORE

Divine Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Explore Cape Sounion
  • Discover the island of Delos
  • Experience Mykonos
  • Enjoy Santorini
Starts / Ends:
Delos / Sifnos
Activities:
Hiking, Small Ship Cruises
Activity Level:
Variable
Embark on an 8-day cruise aboard the Elysium and discover the stunning beauty of the Cyclades. The islands shine with beautiful light and vivid blue colors, surrounded by gorgeous beaches, clear waters, and white buildings. Each island has unique charm and beauty, offering a timeless and peaceful …
Cruise Details
0
Explore the beautiful walkways of Santorini
$4,960
EXPLORE

The Jewels of the Aegean

Antalya - Athens - 8 Day Itinerary aboard L'Austral
  • Visit Kusadasi's fishing village
  • Explore UNESCO World Heritage Sites
  • Discover Patmos's landscapes
  • Sail the Cyclades archipelago
Starts / Ends:
Antalya / Athens
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits
Activity Level:
Relaxed
Set sail on the L'Austral for an 8-day cruise to the southern Aegean's most stunning Greek islands, and take in the archipelago's rich cultural history and cool, turquoise waters. Explore Antalya's Roman port, medieval Rhodes, mythic Patmos, and the historic fishing village turned …
Cruise Details
0
Walking in Santorini
$2,030
EXPLORE

Southern Cyclades

8 Day Itinerary aboard Star Clipper
  • Explore beautiful Rhodes
  • Visit Halicarnassus
  • Discover breathtaking Santorini
  • Ride a donkey to a lookout point
Starts / Ends:
Piraeus / Piraeus
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
The Star Clipper brings you closer to unique island cultures, ancient treasures, and the breathtaking beaches of Greece on a spectacular 8-day cruise. History lovers can seek out ruins, both ancient and from the Crusades of the Middle Ages. Shoppers can have a field day in the stores and galleries, …
Cruise Details
0
1-7 of 7 Results
TrustScore 4.8 | 382 reviews
TrustScore 4.8 of 5
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Based on 382 reviews on
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1 day ago
The booking was processed efficiently and quickly. We got what we wanted.
Doug Laporte
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1 day ago
Great company. Good communications. Great accommodations, excursions, transport. Guide Elvira was spectacular along with transport, driver, Cesar and activities
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2 days ago
Very responsive to questions. Helpful with all arrangements
Roz
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3 days ago
The ship company they sent us on was perfect in every detail
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4 days ago
I’m so glad we found AdventureLife. Jess, our planner, was such a pleasure to work with. She readily shared her extensive knowledge about Panama, she offered good suggestions and creative ideas, kept everything organized and handled the details each step of the way.
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