Greek Islands Private Tours

Greek Islands Private Tours and Experiences Hosted by Local Experts

Ignite your sense of adventure with a Context private tour of Santorini or Crete, where you'll immerse yourself in the captivating stories of the Greek Islands and witness the echoes of ancient civilizations. Each island has its own unique character and charm. From 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. The Greek Islands 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
(4.82) 53 Reviews

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The program designed by Dimitra — with the most valuable help from Georgios Korsavvas, our highly qualified driver and special tour advisor — included not only the highlights of Crete (such as Knossos and Phaistos palaces; Archaeological Museum of Heraklion and Eleutherna Museum; Arkadi, Tsagaroloi and Preveli Monasteries; Gortyn, Gournia and Hagia Triada archeological sites, and Matala and Preveli beaches, to mention only a few of the many we visited), but also some very personalized experiences. For instance, we visited the “Shepherd’s Shelter” (https://www.tospititouvoskou.gr/en/) and were guided by Papa Andreas himself, a very peculiar and charismatic individual and a rare combination of priest, shepherd and ski enthusiast, who gave us a rich explanation about life on the Mountains of Crete and offered us the cheese and ouzo (the famous — and quite strong — dry anise-flavored Greek drink) that he produces on his property. Also noteworthy was the tour in the Spinalonga Island, in which, instead of taking one of the touristic boats usually used when people visit the island, we hired a private boat, which allowed us not only to manage our time on the island according to our will (arriving earlier than the tourist groups, for example), but also to sail around the island to enjoy its terrific views and then follow to the nearby Kolokytha peninsula and snorkel over the sunken remains of the city of Olous. Equally remarkable was the traditional pottery workshop with Mr. Giorgis Dalamvelas (https://keramion.gr/en/) in Margarites, an important center for ceramics in Crete, which brought me a deep understanding of this ancient art and its importance in Cretan culture (not to mention a vase I made myself, which turned out well, albeit not very well shaped despite all the help given to me by Mr. Dalamvelas). In sum, it was a fantastic trip with many unforgettable memories!
After having participated in all of Dimitra’s Context Conversations during and after the pandemic, it was a delight to finally meet her in person and find her to be not only a highly experienced guide, but also friendly and witty, and a pleasure to be with. Despite having been born in (her beloved) Athens, she has vast knowledge about everything concerning Crete (history, culture, anecdotal facts, little-known picturesque locations etc.) and the skill to share such knowledge in a simple and interesting way. She was able to contextualize each place we visited in our customized 14-day trip and to point out its historical relevance. She was always more than willing to answer my questions and used each of those moments as springboards to add further points and issues of interest. That said, if you truly want to know Crete and have a fascinating experience on the island, ask for Dimitra!
Dimitra is the quintessential guide, knowledgeable and informative, organized and passionate. She is also a very pleasant person, someone with whom you will always have a good time. As the perfect guide she is, at each site we visited, she gave me a rich description of the venue and its relevance throughout Crete’s history, thus enabling me to better understand what stood before my eyes. She also drew my attention to many interesting and surprising details and instigated me to build connections between what I was seeing and my previous knowledge and experiences. And all of this while keeping a light and fun environment (which was specially challenging considering we toured together for 14 intense days all around Crete and Santorini). In a nutshell: I learnt a lot and enjoyed myself tremendously!
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