Sailing the Greek Islands – Itinerary

Since my objective was to be on a boat, I wasn’t focused on what islands we were on the itinerary. I just wanted to be on the water. I knew I want to go to Santorini and that was what prompted me to book two weeks as it allowed two days in Santorini. The guide I had purchased didn’t do most of the island’s justice and eventually, I decided just to learn on board the boat. That was part of the appeal of the charter company I chose; they provided information every day about the places we were going to visit. Several islands will get an individual post, but I want to give you an idea of each island.

Week One

The first stop was the small island of Aegina. Sailing to Aegina doesn’t take very long, and the captain said that this was because they hope to let passengers get their sea legs, so they don’t get seasick.

Aegina is known for the Temple of Aphaea as it is one of the best-preserved temples of ancient Greece. The temple is located at the top of the island, and you have to hike up to the top. I opted not to climb to the temple because I woke up with a migraine and it was still hot in Greece in September and would have made my migraine miserable. Since the island is also known for their pistachios, I went on a pistachio hunt! Later I decided to bring these back to Qatar for my coworkers, but they were some of the best pistachios I have ever had.

After lunch and swim, we headed to Poros, which isn’t far from Aegina. We docked at the town of Poros (I discovered there are many duplications of names in Greece). This was to be our sleeping spot for the evening. First thing on everyone’s mind was a shower. The local beer pub offered showers for €3! So, yes, I showered in a bar. It wasn’t the nicest shower I have ever had, but it certainly wasn’t the worst. And I definitely think it was part of the experience.

The next island was Hydra. Hydra was a happening place! The port was full, and we had a hard time finding a place to dock. There are no cars allowed on the island, and it is full of cats!

The captain wanted to head to Milos, but the weather wasn’t going to cooperate. Instead, we headed to Kythnos. Kythnos was one of my favorites. We slept in two nights in Kythnos in different places. (There will be more on Kythnos later.)

Next, we headed to Serifos for a short swim stop. The tricky part here is there is no harbor. We were given the option to swim to the beach or take the dingy. I was sure I could make it to shore, but I wasn’t sure I would be able to make it back the boat. I opted to take the dingy. The water was so clear here. It reminded me of the Caribbean.

The next and final stop for the first week was Ios. By this point, I was really tired and decided to stay on the boat that day knowing I still had to do Santorini and another week!  This turned out to be a good thing as I was struck down by the opposite of seasickness, land sickness (?) and was dizzy for several days. There are lots sights to see here, though, including Homer’s Tomb. We had dinner the last evening together at an amazing hotel overlooking the harbor and were treated to a spectacular sunset.

Week Two

After two nights in Santorini, I returned by ferry to Ios to begin week two! The land sickness went away for a bit on Santorini but was totally gone once I was back on the boat. Schinoussa was the next island and had the smallest population of all the Greek Islands we visited. As of 2011, 256 people lived there, but it seemed like less than that. There wasn’t anything at the port, but the walk up to the town was magical as they have made a great stone path that is lit at night. I wish we had more time on this tiny island.

Next, we sailed to Paros. Paros was much larger than Schinoussa and some of the other islands we visited. I decided to strike out on my own for the day and the evening meal. The island had great shopping and restaurants. You could wander the streets for hours. My only regret was that I didn’t have more room in my suitcase. The harbor was not protected, and we had a rough night on the boat and eventually, I went to sleep in the lounge area to try to escape the noise of the water hitting the stern where my cabin was located.

The ancient site of Delos was the next island. Delos is not an inhabited island due to the whole island being an archeological site. It is believed to have been inhabited since the 3rd millennium BC. If you aren’t on a sailing cruise, you can get here by ferry from Mykonos. Bring your hiking shoes and some water as there is lots to see and the only snack shop on the island is a bit of a walk from the port as are the bathrooms!

Another big island was up next with Syros. Syros is very modern and looks a little Italian. It had a nice mix of sites to see and shopping. We had a wonderful dinner here in a building that wasn’t fully restored, and the ceiling was made of vines that hung down into the dining room. The food was modern Greek.

Last, but not least was Kea. Kea was another favorite of mine. The harbor was small and quaint. The beach was a short walk from there. We slept at Kea and in the morning went to the hilltop Chora (village) to see the Lion of Kea. Kea has a wonderful museum in the village as well.

Are you tired yet? I was by this point and was glad and sad to be heading back to Athens. While I think I would have needed some serious naps, I would have loved to stay on the boat for the next two-week journey.

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