Travel Diary – the Cyclades, part 1

So my family recently went to Greece. It was our first time going as a family (my parents went for their honeymoon 24 years ago) and it was our first time out of the country as a family for a long time. We found out about this company called G Adventures that do guided tours and such and they have a week-long sailing one through Greece. I decided that my brother and I were going to do it (he was out of town and we had to book soon to figure flights/hotels out). So we did and it was the greatest decision ever.

The tour is recommended for those aged 18-35, but anyone over 16 can do it. The boat can hold 8 people plus the skipper. Our main concern was that we’d get stuck with shitty people, which would ruin the trip. I actually had a nightmare about it the night before. Luckily for us, the rest of the group was fantastic. There were five other girls aged 18-32 and we all got along really well. Our skipper, Julle (pronounced like Julie but with a Y) was the greatest. He’d been doing the tours for so long and was super chill and put up with all of us. The people definitely helped make the trip 1000000x better than I’d hoped for.

So onto the actual trip. The trip was 1 week long and we were to sail from Santorini to Mykonos. The itinerary was super chill, which allowed us to make changes depending on the weather. We ended up going to six islands and they were all different but similar. They were all so beautiful, I don’t think I’ll ever get over it.

Day 1: We met up with our group on Santorini and spent the night there. We went to this tavern there, Dmitiri’s Taverna. There was singing and dancing by Dmitri and his son. The food was great. It was a pretty great night.

Day 2: This day was honestly basically perfect. That morning we went swimming at Oia, which was beautiful. It’s seriously so cool how they build the buildings into the rock. The weather was perfect, the water was beautiful, we couldn’t have been in a more beautiful place.


After swimming, we went to Koufonissia, which is one of the smaller islands. There’s only about 350 people that live there. It was one of my favourites for sure. Once we had docked, we biked to a beach. The bike ride was supposed to be a slight uphill. If a Greek ever tells you this, be prepared for it to be uphill the entire way. It was literally uphill the whole way both ways. But it was so worth it. The water was so clear, it was deceiving. You’d think it was super shallow and you could touch, but it was at least 10 feet deep.


We went to this family-run restaurant for dinner. In classic Greece style, it took forever to get our food. At one point Julle stood at the kitchen and stared down the cooks until they had out food ready. But it was really good, so we forgave them.


After dinner, we went to a couple bars. The first one was a little hole-in-the wall kinda place which was super chill. My margarita was basically just tequila and triple sec dyed green with a lime in it, so I couldn’t drink it (I’m a wimp). But we played limbo and chilled outside and had a great time. Then we went to a more modern bar that was run out of one of the classic windmills you see. We got classic fruity drinks and some lady bought us whipped cream and oreo cake and we made fun of Julle and laughed so much he couldn’t tell us anything. It was a perfect, perfect day.

Day 3: When we woke up, we found a little bakery and got croissants for breakfast before sailing to Paros. We got to Paros around lunch-ish and went to a cafe for coffee and milk shakes. We then took the bus to Naoussa and went to the beach. It was incredibly beautiful and so picturesque.


We then went to Parikia for dinner and to explore the streets. I wish we’d spent a little less time talking at the beach and had more time to wander around Parikia. But we got to watch the sunset while we ate dinner, so I can only complain to much. We went to this restaurant that was run by this adorable old man who had lived in Canada for a while. The food was fantastic as well.


It was also a practically a perfect day. We had such a great conversation on the bus back to the port. I cannot express how grateful I am we had a good group.

Because this post is getting long, I’ll continue the rest of our trip in another post. Let me know if you’ve ever been to the cyclades and what your favourite was.

Thanks for reading!

4 thoughts on “Travel Diary – the Cyclades, part 1

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