Greek Islands in Two Weeks

At the beginning of the summer I went on vacation for two weeks with my boyfriend in the Greek islands. It was magically beautiful, the food was delicious and the people were incredibly welcoming. An absolutely MUST visit location!


Here is my recap of the trip, including some links of where we stayed, and some tips about how to plan your very own Greek vacation.


We flew in to Santorini, our flight arrived late afternoon, and we took a cab to our AirBnb. We opted to stay on the opposite side of Santorini (opposite of Oia), because it is far less touristy, way more affordable, and so much more authentically and traditionally Greek. Our AirBnb was absolutely adorable and so perfect for our first few days in Greece. Walking around Akrotiri that first night felt so nice. We had finally arrived at our destination and we were ready to indulge in our first bites of delicious food and drink some wine.


On our first morning, we trekked down a very precarious path to the beach and made it to Red Beach, which, as you can see in the picture above, is true to its name.

The next day we rented a car and drove to a nearby vineyard, Boutari, for a tour and wine tasting. It was so fun and delicious and so worth the price, which wasn’t high at all. To sample four different wines and appetizers and have a tour of the winery cost 15 euros per person. I would highly recommend a visit there if you are on Santorini.



Going to the Greek islands means going to Oia, the most touristy part in all of the Greek Islands, and possibly all of Greece. It is where so many movies have been filmed, including The Sisterhood of the Traveling Pants. It is where you will be able to admire the stereotypical blue roofs and white walls. Oia is drop dead gorgeous and it is definitely worth seeing. However, prepare yourself to be absolutely packed liked sardines in the small streets of Oia, to pay outrageous amounts for food and beverages and to get annoyed very quickly when everyone is crowding around the same areas to take pictures.

However, as crowded as it can be, the sunset views from Oia are absolutely breathtaking. It’s worth the drive across the island to even look at the sun setting for just a few minutes. I believe the picture speaks for itself (unedited).



After a few days in Santorini, we took a ferry to Naxos. Waiting in line for over an hour in the heat with our heavy bags on our backs was one of the most unpleasant experiences ever. There was no clear order, no boarding priority, just a very large crowd in a free-for-all situation. Next time I’d be more likely to fly out of Santorini to avoid that nightmare.

However, once we arrived on Naxos everything was alright again! There was right away a totally different vibe from Santorini. The port was quaint, lovely and was lined with a variety of restaurants, bars and shops. We made our way by foot to our AirBnb that was absolutely perfectly located. We were within walking distance to everything in the main centre of Naxos. Our host was so lovely and the apartment was clean, modern and very cozy. Plus, they offered free laundry services, which is such a great bonus to have during a long trip abroad.


Walking around Naxos at sunset is so pleasant. The streets are not very crowded and the atmosphere is very nice. We were able to find a cute little restaurant and tried some traditional Naxos dishes, including some yummy potatoes.


One thing to take note of on the Greek islands is the overwhelming amount of stray cats. I’m used to traveling and encountering stray dogs, but in Greece cats are the majority animal in the streets.

We rented a car on Naxos and drove around the entire island to find beautiful beaches and more beautiful spots to photograph. Driving around allowed us to stop whenever we wanted, especially when the beach looked good and was empty. This allowed for some cheeky photoshoots and some fun sunset pictures on the beach. Having a vehicle was definitely an asset and I would highly recommend a car over an ATV on this island due to its size.




Another very well-known island and therefore a very pricy option for a holiday destination. Thank goodness we were only there for three nights because we would have gone broke from the sheer expensiveness of the island.

Mykonos is beautiful, there is no doubt about that, but so are all other Greek islands in my opinion. Mykonos is the place where rich Europeans go to rent large extravagant villas and party on the beach. Not exactly what my idea of a good time is and that is why Mykonos was my least favourite island.

Walking around downtown Mykonos is an absolute dream. I wanted to take pictures of everything and be photographed everywhere, but it’s a very difficult thing to accomplish when there are at least ten different people in every shot. Lots of tourists flock the streets of Mykonos and make it difficult to navigate.


We did indulge in some delicious Greek dessert, Loukoumas (pictured below). That was a big highlight of the trip and I would recommend to anyone going to Greece to sample these fried balls of goodness.


The most expensive place we stayed during the entire trip was our hotel in Mykonos. I will not link it because I would not recommend anyone stay there as we did not have a very pleasant experience. It had beautiful views of the beach, but that’s about it.


In Mykonos was the first time we were able to rent an ATV. For foreigners it is required that you have an international driver’s license (which can be purchased online). We had so much fun with our “Mighty Mouse” and we definitely took it all around the island to explore as much as we could. Just to add a note here to assure you that while driving around we did have helmets.



Our last island was Syros. It was both our first time on this island and we were ready for something new, different and inexpensive. Syros won over our hearts very quickly and we would return in a heartbeat.

We rented another ATV in Syros and had lots of fun driving around and discovering yet another beautiful island.


During our time on Syros, we had lunch at the same little restaurant a couple beaches away. We enjoyed our delicious Greek salads and gyro wraps so much that we had no other option but to return three times.

Sunsets and general views from our beautiful bed and breakfast were stunning ! We stayed in Kini Beach up on a hill. It was by far the best place we stayed.


We also explored the streets around the port and had the benefit of witnessing a military helicopter demonstration, which was very cool to watch!


Our journey home from Naxos was extremely long and very tiring. Next time I would cut it down and we would probably stay in Athens one night before flying all the way back to Calgary.


I hope you all have enjoyed reading about our time in the Greek Islands.

If you have any blog post suggestions please comment down below.

Have a wonderful week everyone !



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