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Top Greece Trips & Tours in May 2026

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Discover Greece in May 2026 on one of these 10 tours hand-selected by the travel experts at Adventure Life. Explore the best of Athens, Mykonos, Santorini, Nafplion, and Delos during May 2026 as you enjoy archaeological site visits, cruises, village visits, small ship cruises, and cultural. Prices for trips in May 2026 range from $2,263 to $25,176 for a vacation of 7 to 13 days. Choose any of the below 10 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Greece trip planners.
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Greek Monastery on a Rock and Sunny Summer Evening
$4,287
EXPLORE

Highlights of Classical Greece

7 Day Itinerary
  • 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
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Local Market Visits, Urban Exploration, Village Visits
Activity Level:
Relaxed
Embark on a journey through the ancient world on a 7-day classical Greece adventure from Athens. Discover the rich cultural heritage of Athens as you visit its famous landmarks, including the Acropolis and Parthenon. Explore the picturesque town of Nafplion, the first capital of Greece, and marvel …
Tour Details
0
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
See the ancient world come alive in Athens
$2,262
EXPLORE

Athens City Explorer

4 Day Itinerary
  • 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
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Urban Exploration, Village Visits
Activity Level:
Relaxed
Experience the best of Athens with the 4-day Athens City Explorer tour. With the help of an experienced guide, this immersive and comprehensive tour will take you on a captivating journey through the rich history, culture, and landmarks of the ancient city of Athens. Encounter a vast collection of …
Tour 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
Sunset over Athens' port
$2,410
EXPLORE

Delightful Dervishes

Piraeus - Istanbul - 8 Day Itinerary aboard Star Flyer
  • Discover Piraeus’ vibrant gateway
  • Explore Mykonos’ charming harbor
  • Visit Patmos’ serene monastery
  • Experience Chios’ mastic heritage
Starts / Ends:
Pireaus Port / Istanbul
Activities:
Local Market Visits, Small Ship Cruises, Wine Tasting
Activity Level:
Variable
Embark on an 8-day cruise from Piraeus to Istanbul aboard the Star Flyer, blending ancient history, vibrant culture, and scenic beauty. Begin in Athens, exploring its timeless landmarks before setting sail from Piraeus. Discover cosmopolitan Mykonos with its charming harbor and lively tavernas, …
Cruise Details
0
Ruins Athina Pronaia temple in Ancient Delphi
$15,696
EXPLORE

Mediterranean Wonders: Sicily, Greece, Sardinia, and Beyond

Spain - Greece - 13 Day Itinerary aboard National Geographic Orion
  • Cruise the Mediterranean Sea
  • Explore standing stones on Menorca
  • Taste Sicilian wine
  • Swim at Kefalonia
  • Explore Delphi and Corinth Canal
Starts / Ends:
Barcelona / Athens
Activities:
Small Ship Cruises
Activity Level:
Variable
On this 13-day Mediterranean Wonders: Sicily, Greece, Sardinia, and Beyond Cruise from Spain to Greece aboard National Geographic Orion, traverse the Mediterranean Sea to explore ancient ruins, medieval towns, and culinary delights from Spain and Sardinia to Corsica and Greece. Walk among …
Cruise Details
0
kalymnos
$3,590
EBD
EXPLORE

Hidden Greece: Unexplored Greek Islands

8 Day Itinerary aboard Panorama
  • Discover Kalymnos
  • Enjoy views of the Aegean Sea
  • Learn about the island of Patmos
  • Explore the villages of Ikaria
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits
Activity Level:
Variable
Board the Panorama for this 8-day Mediterranean cruise to the legendary Greek Isles. Explore stunning island destinations that offer a taste of true Greek culture. These are places where people take pride in offering hospitality, and where things are done with love and soul. Discover hidden gems …
Cruise Details
0
Explore the ancient Acropolis
$696
EXPLORE

Athens Snapshot Extension

3 Day Itinerary
  • 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
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Village Visits
Activity Level:
Relaxed
Experience the magic of Athens on this 3-day extension to your time in Greece. Start your journey by visiting the iconic Acropolis and Parthenon, two of the most famous ancient sites in the world. Admire the impressive architecture and learn about the rich history of these iconic landmarks. …
Tour Details
0
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