🎂 Context is 20! Learn more and find out what’s new in our 20th year. 🎂
Greek Islands Private Tours

Greek Islands Private and Small Group Walking Tours

( 12 )
Ancient archaeology, vibrant villages, world-class olive oil, and exciting local wines, there is much more to the Greek Islands than just another beautiful beach! Explore the islands of the Aegean Sea with a Context expert.
Whether visiting as a day trip from a cruise ship or as part of an extended stay on one island, our Greek Islands private tours offer a range of sites and activities for all ages and interests. With 6,000 islands to choose from, there is something for everyone. Learn about the original inhabitants of these scenic and strategically placed islands: as early as 3000 BC, ancient Cycladic and Minoan civilizations called the archipelago home. We can trace the long years of foreign rule - Roman, Byzantine, Ottoman, and Venetian rulers left their imprint on the islands. On one of our Greek Islands private tours of Mykonos, Santorini, or Crete, together with a local historian or archaeologist, we will dive into the history of this picturesque archipelago and gain an understanding of the role of this network of islands in the development of Western civilization as we know it today.  

Greek Islands Private Tours

Each island has its own unique character and charm. From the cooling breezes and sweeping vistas of Mykonos to the dramatic black volcanic sand beaches of Santorini to the traditional villages that feel lost in time on Crete, the array of island options is staggering. We have made a selection that offers the best of the best: Mykonos, Santorini, and Crete offer breathtaking scenery, fascinating archaeological and historical sites, traditional foods, and delicious wines. On our Greek Islands private tours, our local experts will take you off the beaten track, away from the crowds, to get below the surface of these magical isles. 
What Context Greek Islands Travelers Say
12 Reviews (5.0)

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Dmitra was wonderful and did a terrific job. There was a general strike and the museum was not open so she came up with several options for a Plan B and we had a great day. She was incredibly knowledgeable as well as energetic and interesting. We thoroughly enjoyed the palace of Knossos and she made it come to life. Yanni our driver was also great. This was a highlight of our trip to Greece
Extremely knowledgeable and personable
Imagine exploring Crete with an archeologist who’s studied the island’s ancient sites. Better yet, an archeologist with a side gig as an actress. We completely lucked out with the knowledgeable- and hilarious - Dimitra Pilarinou. We did 6 full-day excursions with Dimitra. She expertly guided us at Knossos and other Minoan sites, Roman ruins, Venetian ports, Greek Orthodox monasteries and village chapels. Dimitra shared fascinating history & stories about each. She even took us on a boat to Spinalonga, the island leper colony made famous by the soapy novel The Island, and shared the island's Venetian, Ottoman, and Cretan history. But Dimitra also lives in Crete and gave us local insight. She showed us the local food market, guided us to local producers of olive oil, wine, herbal remedies, and the best bougatsa. Dimitra treated us to Cretan cheese pies and recommended restaurants in Heraklion. She even recommended a quiet secluded beach to chill out after our week of packed exploring. Dimitra’s time, plus a professional driver, is pricey. But entirely worth it if you want a memorable deep dive on the ancient, medieval, and modern history & culture of Crete, with a master storyteller and teacher. She’s fluent in English & Spanish.