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Greek Islands Private Tours

Greek Islands Private and Small Group Guided Tours

( 5 )
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. 

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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. Our team of expert planners will work with you to design a tour that fits your interests and time frame, from a half-day walking tour to a multi-day itinerary to cover all the highlights.
What Context Greek Islands Travelers Say
5 Reviews (5.0)

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Full-Day Excursion to Zaros + Private Cooking Class. What you did right: Your guide Dimitra, our driver Adonis and the cooking class experience were fantastic A moving experience to visit The monastery of St Anthony at Vrondisi and the Venetian Adam and Eve Fountain! Dimitra Pilarinou, was outstanding in describing the importance of the monastery in the resistance from the Turks, the beauty of the frescoes, and the Cretan school of painters. A most stop on our way to Zaros village where we had our cooking lesson. We stopped briefly at lake in Zaros to meet our contact who guided us to Zaros village and the cooking class. The class was outstanding! We were greeted by the husband and wife cooking team who prepared a beautiful table with fresh juices and Cretan sweets to welcome us, a great pick me up after our long trip. Each one of us received a traditional Cretan apron with our names embroidered! A very sweet touch! During the next several hours, we learned to make many traditional Cretan dishes – we worked as a team and learned a lot! At the end we had a fantastic feast of stuffed vegetables, Greek salad, lamb and goat stew, stuffed grape leaves and Cretan wine. For desert we had orange cake and all sort of candied fruits. As we were saying our goodbyes, we received a beautiful goodie bag with homemade olive oil, raki, rusk and all our recipes! This is a must experience! A magical place What you need to improve: Context Itinerary was not well put together. Same copy was copied and paste everyday. Why was the same location photo used every day? And where was that photo taken? Dimitra had provided day trip photos on her original proposal that could have been used. My kids have not seent he original proposal and having photos of the places we were going could have been helpful The Transfer to Samaria Gorge via Sfakia + boat instructions were left out. Yiannis the driving company was kind enough to print a copy of the instructions for us. The itinerary going forward should be done with the in-land guide to be sure all information is included.
Full-Day Excursion to Knossos Palace, Paterianakis Winery, & Archanes Village What you did right: Knossos Palace is where Dimitra Pilarinou shined! Because of Covid traveling restrictions, there were very few visitors in Knossos, so we were able to linger in places and go in depth on the Minoans culture and engineer achievements. Dimitra had wonderful photos to share with us that aided her stories and were able to place the artifacts and murals we saw at the Archeological museum at the Knossos site. An architectural marvel and the #1 tourist attraction in Crete. Paterianakis Winery: I think having a winery on the tour is a great idea as wine is so integral part of Crete’s ancient past. Paterianakis Winery is an award winning winery, women owned and meticulously care for. We did not had a winery tour, originally part of the description, some of my family members were disappointed. The lunch was good, not exceptional. Some dishes were cold. Archanes Village: We loved it! It is an ancient Cretan village filled with charm. We enjoyed walking the village very much This was a perfect day! What you need to improve: Request e-mails for excursion reviews from Context should arrive at the end of all the experiences, not daily. We had a 7 hour difference and a packed itinerary and could not review the experiences daily.
Full-Day Excursion to Spinalonga & Agios Nikolaos. What you did right: Dimitra Pilarinou, was exceptional at this excursion explaining the many historic periods, invasions, influences in the Crete. We started our journey with a stop at the Saint George Selinaris Male Monastery built in the heart of the gorge Selinari and with fantastic frescoes and views. At the town of Agios Nikolaos we boarded a small fishing boat to the island, taken back the beauty of the landscape. We walked the whole island with Dimitra and we visited the surviving houses and graves of the lepers that habited the island after the Venetians and Turks were expelled from Crete around 1903. Through out the day, Dimitra explained the discrimination of lepers in Crete, the invasion of pirates in the island, Victoria Hislop’s book “The Island” We finished our day with a fabulous lunch near the sea at family owned Taverna Spinalonga were we ate the catch of the day. We did not had time to see Agios Nikolaos town, but it was OK by our group. This happens to be one of my favorite days in Crete What you need to improve: Daily reminders from Context: They were a great idea, but they sometimes arrived too late in the day. it would be great if ALL expenses could be covered. It was somewhat confusing to have some entries paid and other not.