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Top Greece Trips & Tours in May 2027

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Discover Greece in May 2027 on one of these 9 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2027 as you enjoy Archaeological Site Visits, Village Visits, Local Market Visits, Hiking, and Wine Tasting. Prices for trips in May 2027 range from $2,500 to $41,390 for a vacation of 8 to 11 days. Choose any of the below 9 itineraries in May 2027 and customize it when you contact one of Adventure Life's expert Greece trip planners.
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Explore colorful villages on Rhodes
from $14,990
EXPLORE

Greek Islands & Turkish Coastline

Roundtrip Athens - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Athens' sophistication
  • Discover Delos' mythological past
  • Experience Mykonos' whitewashed
  • Visit Patmos’ sacred cave
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on an 8-day cruise from Athens aboard the Emerald Azzurra, discovering Greece and Turkey's coastal gems. Experience ancient sites like Delos and Mykonos, enjoy leisure in Santorini, and explore local markets, all while relaxing on your luxurious yacht.
Cruise Details
0
Visit charming Naxos
from $3,415
EXPLORE

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
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
Relax on the sunny beaches of Paros
from $3,415
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Mythical Aegean Adventure

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Explore Delos historic ruins
  • Wander Mykonos lively alleys
  • Visit Kusadasi ancient Ephesus
  • Swim Paros secluded bay
Starts / Ends
Lavrion / Lavrion
Activities
Snorkeling
Activity Level
Variable
Experience an 8-day cruise on the Elysium, sailing the Aegean Sea from Mykonos to Kusadasi and Ephesus. Enjoy historic sites, traditional cuisine, and the vibrant culture of the islands while relaxing on stunning beaches.
Cruise Details
0
Sail the Mediterranean
from $2,500
EXPLORE

Greek Island Odyssey

Piraeus Roundtrip - 8 Day Itinerary aboard Star Flyer
  • Walk Ancient Athens landmarks
  • Explore Karpathos Harbor
  • Visit Ephesus Ruins
  • Explore Patmos Heritage
Starts / Ends
Athens / Piraeus
Activities
Small Ship Sailing
Activity Level
Variable
Sail for 8 days aboard Star Flyer on the Greek Island Odyssey through the Aegean Sea. Travel from Athens to Karpathos, Rhodes, Kusadasi, Patmos, and Andros, balancing iconic ports, historic sites, and relaxed sailing days before returning to Piraeus.
Cruise Details
0
Explore the ancient Acropolis
from $2,500
EXPLORE

Aegean Gems

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
  • Walk Athens historic Agora
  • Explore Samos harbor ruins
  • Stroll Çeşme white streets
  • Discover Skyros village life
Starts / Ends
Piraeus / Piraeus
Activity Level
Variable
Discover Greece and Türkiye aboard Star Flyer on an 8-day sailing from Piraeus to Piraeus. Visit Athens’ historic Agora, stroll Samos’ harbor, explore Cesme’s streets, wander Skyros’ villages, relax on Skopelos beaches, and experience Poros’ cultural landmarks. Onboard, enjoy pools, lounges, a library, and a spa.
Cruise Details
0
Discover beautiful Symi island
from $2,500
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Authentic Greek Escape

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
  • Explore Athens historic Agora
  • Stroll Fethiye old town
  • Swim near Symi harbor
  • Wander Monemvasia alleys
Starts / Ends
Piraeus / Piraeus
Activities
Archaeological Site Visits, Local Market Visits, Village Visits
Activity Level
Variable
Experience 8 days aboard Star Flyer from Piraeus to Piraeus, exploring Greek and Turkish islands. Walk through Athens’ historic Agora, and visit Fethiye, Symi, Astypalea, Sifnos, and Monemvasia. Enjoy beaches, ancient ruins, local culture, and authentic cuisine while sailing traditional waters of the Aegean and Mediterranean Seas.
Cruise Details
0
Explore beautiful Paros
from $13,000
No SS
EXPLORE

Crossroads of the Ancient World: Exploring Greece and Turkey

Roundtrip Athens - 11 Day Itinerary aboard National Geographic Orion
  • Explore Delos ancient ruins
  • Walk Ephesus ancient city
  • Explore Paros harbor towns
  • Visit Didim Apollo sanctuary
  • Visit Patmos monastery site
Starts / Ends
Athens / Athens
Activity Level
Variable
Explore the Greek Islands and Turkey on an 11-day cruise aboard National Geographic Orion. Travel from Athens and Lavrio to Delos, Patmos, Samos, Ephesus, Bodrum, Leros, Naxos, and Paros. Walk ancient ruins, visit monasteries, explore island villages, sail the Aegean Sea, and experience local culture and history.
Cruise Details
0
Ruins Athina Pronaia temple in Ancient Delphi
from $9,100
No SS
EXPLORE

Ancient Mediterranean: Exploring Greece, Croatia and Albania

Greece to Croatia - 8 Day Itinerary aboard National Geographic Orion
  • Navigate scenic Corinth Canal
  • Explore Delphi Ruins
  • Stroll Dubrovnik Walls
  • Taste Local Wines
Starts / Ends
Athens / Zadar
Activities
Wine Tasting, Hiking, Cooking Classes, Kayaking, Festival Visits, Urban Exploration, Wildlife Viewing, Stand Up Paddle Boarding
Activity Level
Variable
Embark on an 8-day Mediterranean cruise aboard the National Geographic Orion, sailing from Greece to Croatia with stops in Albania, Corfu, and Dubrovnik. Explore ancient ruins, UNESCO World Heritage sites, and coastal cultures on this expertly guided expedition.
Cruise Details
0
kalymnos
from $3,750
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Unexplored Greece: Aegean Islands

Roundtrip Athens - 8 Day Itinerary aboard Panorama
  • Swim Ikaria’s crystal waters
  • Discover Patmos’ spiritual serenity
  • Taste Amorgos’ local flavors
  • Explore Athens' historic grandeur
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.
Cruise Details
0
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