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Top Greece Trips & Tours in May 2026

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Discover Greece in May 2026 on one of these 14 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, Local Market Visits, and Scuba Diving. Prices for trips in May 2026 range from $731 to $25,679 for a vacation of 5 to 13 days. Choose any of the below 14 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Greece trip planners.
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Church in the center of Marpissa, Paros, Greece
from $3,090
EBD 10%
EXPLORE

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
Explore the beautiful walkways of Santorini
from $4,188
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Greece Island Hopping

9 Day Itinerary
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.
  • 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
Tour Details
0
Explore the ancient Acropolis
from $731
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Athens Snapshot Extension

3 Day Itinerary
Starts / Ends
Athens / Athens
Activity Level
Relaxed
Discover Athens on this 3-day Athens Snapshot Adventure and discover its rich history, vibrant culture, and stunning beauty as Greece's capital city. This unique experience will take you on a captivating journey through the ancient and modern wonders that define Athens, providing you with a comprehensive snapshot of this extraordinary destination.
  • Visit Athens, the capital of Greece
  • See iconic landmark in Athens
  • Take a leisurely walk in Plaka
  • Sample local cuisine in Athens
  • Visit the new museums of Athens
  • See the lovely sea front of Athens
Tour Details
0
Greek Monastery on a Rock and Sunny Summer Evening
from $4,501
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Highlights of Classical Greece

7 Day Itinerary
Starts / Ends
Athens / Athens
Activities
Local Market Visits
Activity Level
Relaxed
This 7-day tour of classical Greece will explore Athens and its rich cultural heritage. Visit the charming town of Nafplion and its beautiful architecture. Learn about Greek mythology and history at the Temple of Apollo and the Delphi Archaeological Museum. Finally, see the stunning rock formations of Meteora and the monasteries perched atop them.
  • Visit Athens, the capital of Greece
  • See iconic landmark in Athens
  • Visit Archaeological site of Mycena
  • See the charming town of Nafplion
  • See iconic site in Olympia
  • Explore Delphi, naval of the world
  • See the rock formation in Meteora
Tour Details
0
See the ancient world come alive in Athens
from $2,376
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Athens City Explorer

4 Day Itinerary
Starts / Ends
Athens / Athens
Activities
Urban Exploration
Activity Level
Relaxed
Embark on a cultural journey through Athens with the 4-day Athens City Explorer. Experience the unique and captivating journey through the ancient and modern wonders that describe Athens. Discover its rich history, vibrant culture, and stunning beauty as Greece's capital city.
  • See iconic landmark in Athens
  • Visit Athens, the capital of Greece
  • Take a leisurely walk in Plaka
  • Visit Archaeological site of Mycena
  • See the charming town of Nafplion
  • See the lovely sea front of Athens
Tour Details
0
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
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.
  • Explore Kea’s charming port
  • Discover Delos archaeological site
  • Visit Monemvasia’s medieval streets
  • Stroll Nafplion’s old town
Cruise Details
0
Enjoy the beautiful blue waters of the Mediterranean
from $5,265
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Saronic Gems

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
Starts / Ends
Lavrion / Lavrion
Activity Level
Variable
Set sail for an 8-day cruise from Lavrion on the Gemaya, exploring the historic Saronic Islands. Enjoy stunning landscapes and rich culture, from the lush charm of Spetses to the UNESCO beauty of Hydra and Aegina's ancient Temple of Aphaia.
  • Explore Epidaurus’ ancient theater
  • Visit Aegina’s neoclassical charm
  • Swim Porto Cheli’s waters
  • Wander Nafplion’s old town
Cruise Details
0
Visit charming Naxos
from $3,335
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Divine Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
Starts / Ends
Lavrion / Lavrion
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.
  • Discover Ios golden beach
  • Swim Naxos crystal waters
  • Wander Mykonos vibrant alleys
  • Explore Delos sacred ruins
Cruise Details
0
Explore the beautiful walkways of Santorini
from $5,265
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Aegean Escape

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
Starts / Ends
Lavrion / Lavrion
Activity Level
Variable
Embark on an 8-day cruise from Lavrion aboard the Gemaya, exploring the stunning Aegean Sea's islands, including Santorini and Milos. Experience picturesque villages, secluded beaches, and rich Greek history amidst breathtaking landscapes.
  • Explore Kythnos thermal springs
  • Experience Sifnos scenic trails
  • Visit Kimolos charming Chora
  • Enjoy Santorini iconic sunset
Cruise Details
0
Colorful flowers and brilliant blue skies complement beautiful Greek islands
from $5,265
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Sparkling Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
Starts / Ends
Lavrion / Lavrion
Activities
Hiking, Scuba Diving, Kayaking, Stand Up Paddle Boarding, Snorkeling
Activity Level
Variable
Embark on an 8-day cruise through the Greek Cyclades aboard the Gemaya, visiting breathtaking islands like Milos, Sifnos, and Delos. Explore pristine beaches, rich heritage, and vibrant culture, concluding your journey at the tranquil marine sanctuaries of Yiaros and Kea.
  • Visit Yiaros and protected wildlife
  • Hike Sifnos scenic trails
  • Swim Despotiko crystal waters
  • Visit ancient ruins in Delos
Cruise Details
0
Sunset over Athens' port
from $2,410
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Delightful Dervishes

Piraeus - Istanbul - 8 Day Itinerary aboard Star Flyer
Starts / Ends
Pireaus Port / Istanbul
Activity Level
Variable
Set sail on an 8-day cruise from Piraeus to Istanbul aboard the Star Flyer. Explore iconic landmarks, vibrant islands, ancient ruins, and serene coastal towns before concluding in Istanbul's cultural splendor.
  • Discover Piraeus’ vibrant gateway
  • Explore Mykonos’ charming harbor
  • Visit Patmos’ serene monastery
  • Experience Chios’ mastic heritage
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
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.
  • Explore ancient Athens landmarks
  • Visit Hadrian’s Roman gate
  • Discover Rhodes medieval history
  • Tour Butrint’s ancient ruins
Cruise Details
0
Ruins Athina Pronaia temple in Ancient Delphi
from $16,172
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Mediterranean Wonders: Sicily, Greece, Sardinia, and Beyond

Spain - Greece - 13 Day Itinerary aboard National Geographic Orion
Starts / Ends
Barcelona / Athens
Activities
Land & Sea Exploration
Activity Level
Variable
On this 13-day Mediterranean Wonders Cruise from Spain to Greece aboard National Geographic Orion, explore ancient ruins, medieval towns, and culinary delights. Visit Menorca's prehistoric stones, savor Sicilian wine, swim in Kefalonia's waters, and explore Delphi.
  • Cruise the Mediterranean Sea
  • Explore standing stones on Menorca
  • Taste Sicilian wine
  • Swim at Kefalonia
  • Explore Delphi and Corinth Canal
Cruise Details
0
kalymnos
from $3,690
EBD 10%
EXPLORE

Unexplored Greece: Aegean Islands

Roundtrip Athens - 8 Day Itinerary aboard Panorama
Starts / Ends
Athens / Athens
Activity Level
Variable
Sail on an 8-day cruise aboard the Panorama, exploring 10 hidden Greek islands. Discover crystal waters, rich history, and authentic culture, where hospitality and passion are timeless traditions.
  • Swim Ikaria’s crystal waters
  • Discover Patmos’ spiritual serenity
  • Taste Amorgos’ local flavors
  • Explore Athens' historic grandeur
Cruise Details
0
1-14 of 14 Results
  • 1
TrustScore 4.8 | 547 reviews
TrustScore 4.8 of 5
total score
Based on 547 reviews on
review score
4 weeks ago
Our trip to Greece was memorable. Adventure Life arranged for a private driver and daily tour leaders who were knowledgeable and personable. The day we were supposed to return, Greece had a 24-hour strike. Elma handled all the transportation problems promptly. I love that Adventure Life has people with experience in different parts of the world, plus local contacts.
JoAnn H.

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