Last Updated on 06/24/22 by Rose Palmer
My luxury Mediterranean sailing cruise took me to some of the most beautiful islands in Greece. Our itinerary combined the classic Greek islands of Mykonos and Santorini with some of the less touristy islands like Syros, Kos, Patmos and Milos.
With about 200 inhabited island in Greece, there is a lot of holiday beauty to choose from. My sailing cruise with Running On Waves took me to a few of them, and with a full day in most of the ports of call, I had time to explore each island and get a feel for its character.
Discovering the most beautiful islands in Greece
I discovered that each island is unique and quite different from the others, especially when it comes to architecture and history. However, all the islands had one thing in common – they all had really good ice cream.
A Day On Syros Island
My first view of the island of Syros was the town of Ermoupolis and its two building clad hills, each one topped with a church – one Roman Catholic and the other Greek Orthodox.
The harbor front was lined with numerous restaurants and cafes. A couple of blocks inland I found the marble lined Miaoli Square with its beautiful neoclassical Town Hall.
When I first walked through the Miaoli Square in the middle of the day it was quiet and empty. An ice cream shop nearby offered a particularly pleasant break from the midday heat. But once the sun started going down, the square and the surrounding cafes came to life as locals enjoyed meals and drinks and kids kicked a soccer ball.
It was a pleasure to explore the little cobbled streets between the harbor and the town hall. They were filled with cute shops, cafes and restaurants. Not far was Agios Nikolaos, the town’s beautiful main church. The church and the Vaporia neighborhood nearby were also built in the neoclassical style by the wealthy shipping merchants that settled Syros in the 19th century.
Once the heat of the day subsided, I started climbing the many stairs up the hillside toward the catholic church of Agios Georgios. As I climbed, the streets got narrower and I knew I was passing through Ano Syros, the original old town on the island that was established high on the hillside in 1200 by the Venetians.
Once I reached the top of the hill and the church, the view over the town and the harbor were spectacular. This certainly was a very pretty Greek island.
Ancient Delos Half Day Tour
The island of Delos is one of Greece’s UNESCO World Heritage sites and is one of Greece’s most important archeological sites as well.
Delos was inhabited as long ago as 3000 BCE. It eventually developed into a spiritual center for the ancient Greeks when it became known as the birthplace of the twin gods Apollo and Artemis.
Over the centuries, a thriving metropolis evolved with a large Sanctuary to Apollo as well as numerous other temples, marketplaces and houses. Its location in the Aegean also made it an important commercial center.
To maintain the religious purity of the island, a decree was put in place in the 5th century BCE that no one could be born or die on Delos. That law still exists today.
Delos thrived for many centuries, but ultimately declined and by the 2nd century ACE was uninhabited and then ultimately became a haven for pirates. The ancient ruins were discovered in 1873 when the French School of Archeology began excavating the site.
The island of Delos can only be visited as a day trip and is a short 30 minute boat ride from the island of Mykonos. Because of its small size, Running On Waves was able to dock in the harbor at Delos first thing in the morning. This allowed our group to tour the site before the majority of the day trippers arrived, and while it was still somewhat cooler.
Our tour guide took us through the major sections of the archeological site and made sense of the jumble of rock piles and the occasional still standing columns. She provided context and described the colorful history of the island. I highly recommend touring Delos with a guide to help understand what you are seeing and why it is important.
Mykonos sightseeing
After visiting Delos, my sailing cruise with Running On Waves continued on to the beautiful Greek island of Mykonos.
Our boat anchored off the island of Mykonos in the afternoon which gave me the rest of the day and evening to explore this popular island and town. Mykonos is one of the Cycladic islands with the typical white houses and blue trimmed highlights.
There aren’t a lot of specific attraction in Mykonos – this island is just about enjoying the atmosphere. I started by just wandering the narrow lanes and checking out the cute shops.
One of Mykonos’ well known sights is the area along the waterfront called Little Venice. These picturesque old buildings glow in the late afternoon sun. I think a drink or a meal at one of the nearby waterfront restaurants would be a pleasant way to enjoy the classic view.
Not far from Little Venice were Mykonos’ most popular sight. I finished the day with sunset views from Mykonos’s famous windmills. The oldest of the windmills on the island is from the 1700’s. At one time these mills were used to grind grain into flour for the local population. Today the windmills are a favorite tourist destination and you can even stay in some of them.
This is an extremely popular spot for sunset and I shared the view with a few hundred other tourists.
Patmos Island Tour
Patmos island has another of Greece’s UNESCO World Heritage sites. The island is best known for the cave where John the Apostle received the visions that led him to write the Book of Revelations, the last book of the Christian New Testament bible.
Dominating the skyline and standing guard on top of the hill over the old town of Chora is the Monastery of St. John. The fortress-like monastery was built in 1100 ACE and was dedicated to St. John the Apostle. This imposing building that looks more like a castle than a religious establishment was designed to repel the threats of pirates and invading Turks.
Our Running On Waves cruise director set us up with a small group bus tour with a guide to see the Cave of the Apocalypse and the Monastery of St. John. This was a very welcome option since I really did not want to walk uphill for an hour on a 95°F day.
The first stop was the building that holds the sacred cave. The cave has been turned into a shrine and is part of a chapel built around the cave (no photos inside). The chapel is used for regular worship services and is decorated with the usual Greek Orthodox icons and other religious paraphernalia.
A short ride uphill then took us to the imposing Monastery of St. John. The monastery is still actively used by the monks that live there, so only the chapel and the museum were open to us.
The chapel was beautifully decorated with frescoes both inside and out. The museum was also quite interesting as it has a number of important and very old Christian artifacts.
After the tour I explored the harbor town of Skala and grabbed a good Greek lunch at one of the waterfront restaurants. Our guide mentioned that even though Patmos gets a lot of tourists, it is a quiet island due to its religious associations. I certainly got that sense as I strolled the lanes of Skala.
Discovering Kos Island
Kos is one of Greece’s westernmost islands and is just a stone’s throw form Turkey. It is a popular beach resort destination with the resorts looking much like the ones I had seen on the Turkish coast.
The island also has a long history dating back to Neolithic times and is best known for being the birthplace of Hippocrates, the father of medicine. For those that love historic sights (like me), the island has many Greek and Roman archeological ruins and also the well preserved remains of a 15th century knights’ fortress.
I started my day in Kos with a tour of Nerantzia Castle. The castle was built by the knights of St. John to protect the harbor. I could still see the remains of the outer and an inner castle that was built from local stones, including recycles stones from the ancient Greek and Roman era site on Kos.
I then spent the rest of my day going from one archeological site to another within the town of Kos. I explored the huge Agora, the Ancient Gymnasium, the Altar of Dionysus and the Roman Odeon as they were all within easy walking distance of the harbor.
It was fascinating to see the blend of these ancient, crumbled ruins surrounded by modern apartment buildings and businesses.
Read my full post about how to see the best sights in Kos in one day.
Exploring Romantic Santorini
The island of Santorini is the poster child for Greece tourism and would certainly be considered by many as one of the most beautiful Greek islands. The town of Oia, with its white buildings and blue trim, offers the iconic Greek island pictures that everyone is searching for.
We had a full day in port which gave me lots of time to discover Oia. The island of Santorini is actually the remains of a volcanic caldera that was formed after an enormous eruption 3600 years ago. Oia and some of the other towns cling to the top of the cliffs, glowing white against the dark brown of the volcanic rock, like icing on a chocolate cake.
The port where we docked was below the main town of Fira. You can walk up the switchback trail to town, or take a donkey up the steep cliffside, but the easiest way to the top is to take the cable car.
It was a quick 10 minute walk from the cable car to the main bus station in Fira where I caught a bus and 30 minutes later arrived in Oia.
There is one major walkway that follows the edge of the caldera in Oia and I strolled along this throughout the whole length of town, window shopping, taking photos and trying out a few of the restaurants. Since it was very hot and there was no shade, it was nice to take frequent short breaks for food, drinks and ice cream.
As I walked along the edge of the caldera in Oia, it was easy to get the classic photos for which Santorini is famous. It certainly lived up to its reputation as one of the most picturesque Greek islands in the Aegean.
To get back to the boat, I just reversed my trek, taking the bus back to Fira and then the cable car back down to the dock and the waiting tender.
A Day On Milos Island
Milos is another of the Cycladic islands, but not as famous (yet) or quite as busy. The most recent Travel and Leisure survey named Milos the best small Greek island as it topped their list of best islands in the world.
Another tour set up by our cruise director took us to the highlights of Milos, of which there were many. Milos is known for its many beautiful beaches, especially Sarakiniko beach which is especially photogenic with its wild, white lunar-like landscape. Wind, water, and time have eroded this volcanic rock into fantastic formations that look like they might belong on the moon.
Milos is also best known as the location where the famous Venus de Milo statue was found, which now sits in the Louvre. Our tour took us to the farmer’s field where the statue was discovered in 1820.
Typically, Milos has a few ancient sites, such as an old Roman theater, catacombs and the remains of a Venetian castle.
Next we spent some time exploring the lanes of the main town of Plaka. Like on the other Cycladic islands the architecture here was the typical blue trimmed white houses, though unlike Mykonos and Santorini, it felt much quieter and laid back.
Our tour finished with time at one of the many beautiful beaches that Milos is know for. It was such a pleasure to take a refreshing dip in the Aegean and to relax on the beach for a bit.
The tour was a great way to get an overview of Milos and showed me that it was certainly the most scenic Greek island that I visited. I would not mind spending more time here next time I visit Greece.
There are a lot of different ways to experience the many pretty islands in Greece. It’s easy to get to all the islands with Greece’s efficient ferry system.
But, a cruise through the islands, especially a small ship cruise like the beautiful sailing ship Running on Waves, is definitely the most pleasant way to visit some of the most beautiful islands of Greece in a short amount of time, and it gave me a chance to experience the many personalities of the Greek islands.
Please note that my cruise was hosted by Running On Waves. All the content and opinions expressed in this post are my own.
Other Greece stories you may like:
Sailing the Greek islands with Running On Waves: Release Your Inner Jackie O On a Luxury Sailing Holiday in Greece
Two days on the island of Hydra: My Lovely Two Days on Hydra Island
Best historic sites on the island of Kos: A History Lover’s Guide to One Day in Kos, Greece
How to visit Mt. Athos: How to Visit Mt. Athos – Even If You Are Female
Thanks for visiting.
Rose
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