7 Perfect Days Sailing the Cyclades in Greece

DestinationsEurope

Mar 22

Greece is the perfect country for a sailing charter. With 227 inhabited islands and many more uninhabited islands, it is best seen by the sea. The Cyclades is our second sailing charter destination in Greece, the serene blue waters and blue skies made for a picturesque backdrop to a relaxing getaway.

Mykonos, Greece

This is where our sailing journey begins and ends. Mykonos is a Greece hotspot and cruise ship destination, so a pretty standard place for a yacht charter to embark and disembark. We arrived by plane from Athens, but there are ferry options also.

Mykonos is known for its beach clubs and its touristy Mykonos Town, which is flocked with cruise ship passengers when the cruise ships are in town, which is nearly every day during the season.

Church of Panagia Paraportiani

The Church of Panagia Paraportiani is one of the oldest churches in Mykonos and dates back to the 1400s. The name of this white-washed church sitting at the entrance to the Kastro area on Mykonos translates to "Our Lady of the Side Gate" in Greek, as its entrance was found in the side gate of the entrance to the town.

The church was not open to visitors when we passed by, but it drew our attention sitting peacefully near the sea.

*Church of Panagia Paraportiani, Mykonos, Greece*

Windmills of Mykonos

The windmills of Mykonos date back to the 16th century and played an important role in the island’s economy by milling grains using the strong winds of the region to aid in the process. Easily recognizable due to their distinctive cylindrical shape, whitewashed walls, and pointed wooden roofs, they are now a tourist attraction and a must-see for those visiting Mykonos.

The perfect time to visit and take pictures is at sunset. If you are staying on island, this is also usually when the cruise ship visitors begin to dissipate.

Delos, Greece

While in Mykonos, we decided to take a ferry to Delos, a UNESCO World Heritage Site and the mythical birthplace of Apollo and Artemis. This is a great option for exploring beyond Mykonos Town and the beach clubs.

Naxos, Greece

After embarking on our catamaran in Mykonos, we headed towards Naxos, stopping in a bay near the uninhabited island of Rineia for an afternoon swim and paddle. Rineia is accessible via daily boat tours from Mykonos, so this is another option for exploring if you are looking for things to do while staying in Mykonos.

Naxos is the largest island in the Cyclades. We moored near the Temple of Apollo Portara, a ruin that resembles what may have been a door or entrance to the temple. It’s situated on the tip of the island with views of the sea and Naxos City.

*Temple of Apollo Portara, Naxos, Greece*

We arrived in the evening in time for dinner and drinks. And then wandered in the city's narrow streets and stone paths for some sightseeing and shopping the next day.

Paros, Greece

After our morning in Naxos, we headed east to our next island destination, Paros. We moored in the bay near Naoussa, which is a hip town with a bustling nightlife. There are fancy wine and liquor stores, trendy boutiques, and cool places to eat. We’d been eating a lot of delicious Greek food, so decided on sushi at UMI Sushi Bar.

The next day, we were advised by the Captain that we had to visit the 4 A.D. Byzantine church, Holy Church of the Virgin Mary Ekatontapyliani while on Paros. This is one of the most well-preserved Greek Orthodox churches and an important Byzantine monument in Greece. The captain took us into port at Naousa near the Venetian Fortress and put us on a private van service to drive to Parakia, the capital and main port in Paros. The reason for the van is that it takes longer to sail than to drive. Once we finished our sightseeing, the catamaran had made its way to the other side of the island to pick us up.

Holy Church of the Virgin Mary Ekatontapyliani

*Alter, Holy Church of the Virgin Mary Ekatontapyliani*

*Baptistery, Holy Church of the Virgin Mary Ekatontapyliani*

Antiparos, Greece

Upon leaving Paros, we didn’t sail too far to our next destination, the channel between Paros and Antiparos. We never stepped foot on the island of Antiparos, but we did watch the windsurfers and sailed by what we believe is Tom Hanks and Rita Wilson’s island home.

We also did some snorkeling on the other side of the island of Antiparos near rocky cliffs with a swim-through cave before we set sail for Sifnos.

Sifnos, Greece

Sifnos is a lovely quaint island with small, picturesque beach towns and villages, and a place I would return to in a heartbeat for a longer stay. This was my favorite island for photos, where everywhere you turn, you want to capture a sight to remember.

We had one of our favorite meals on this trip at Omega3. According to our Captain, this is the place to eat in the Cyclades and he took the liberty to make a dinner reservation for us. For us, this is why these charters are so amazing. We would never have found this island on our own, never mind the restaurant.

*Platis Gialos Marina from a Hillside Church, Sifnos, Greece*

*Hillside Church atop of the Platis Gialos Marina, Sifnos, Greece*

We spent the night in the small marina and the next morning, we headed by van service to Kastro, a small village on the island. Here we passed terraced fields, which we had only seen before in Asia. According to our driver, this is because it was and continues to be an irrigation best practice for hillside farms.

Our driver also explained that Sifnos played a vital role in communicating the news of the Fall of Troy to the Mycenaeans within a day. They used fire lookouts, or phryctoriae, located on the island to send pre-arranged messages. Evidence of at least 76 phryctoriae have been found all around the island of Sifnos.

Upon arriving in the village of Kastro, we headed through the walkways to the Church of the Seven Martyrs sitting atop a cliff against the blue sea. In the village, instead of tearing down old useless structures, they built around the existing ancient structures, including walls and pillars to preserve the history.

*Church of the Seven Martyrs, Sifnos, Greece*

The village had already begun to shut down for the season, so we had the narrow walkways through the village mostly to ourselves. After making our way back to the catamaran, we sailed to another part of the island, Vathi Beach, for a swim and a walk on the beach.

*Our Catamaran at Vathi Beach, Sifnos, Greece*

Serifos, Greece

We arrived in Serifos late afternoon to dine cliffside in the evening. This island presented us with the biggest logistical challenge during the trip, as we needed transport to the cliffside restaurant. The captain was unable to prearrange transport for us but advised that it would not be difficult to get a taxi at the port. This was not the case, as it was towards the end of the season, and not many taxis were available.

After 30-40 minutes, with the help of the crew making phone calls for us, we were able to find transport to the restaurant. We had a lovely meal at Aloni, a Greek Taverna, with mostly locals and some leftover tourists. This was one of the few times we found ourselves at a disadvantage because we prefer to travel at the end of the season. Fewer tourists also means fewer services in some places.

Syros, Greece

Syros ended up being our final island on this trip before returning to Mykonos. We were supposed to make one more stop in Tinos, but the winds were not going to allow this to happen. Just like Odysseus, we were at the mercy of the winds and the sea.

“And if a god will wreck me yet again on the wine-dark sea, I can bear that too, with a spirit tempered to endure.”

— Odysseus

We docked in Ermoupoli, a bustling port city and the capital of Syros, which is easily accessible by ferry from Athens and Mykonos. We docked in the marina here, so could come and go as we pleased without having to coordinate tender transport with the Captain. Because we knew we were not headed to another port, we took our time seeing the sights. We meandered through art galleries, stopped in plazas and cafes for a drink, and popped into boutiques.

We visited two Greek Orthodox Churches, the Church of the Resurrection of Christ and the Church of Agios Nikolaos.

*Church of the Resurrection of Christ, Syros, Greece*

*Church of Agios Nikolaos, Syros, Greece*

At Miaouli Square, we watched the President of Greece, Katerina Sakellaropoulou, and her entourage walk by. We ran into her and her entourage later again that evening at an art exhibition of Seascapes from the Bank of Greece collection. I know nothing of Greek politics, but it was interesting to encounter a Greek dignitary in our travels.

*Town Hall of Ermoupolis in Miaouli Square. Syros, Greece*

Back to Mykonos

On the morning of our disembarkation, we braved the wind and rough seas back to Mykonos. After a week of perfect sailing weather, we now had a bumpy sail back to where we started.

As I reminisce about this trip, I relish the memories of warm breezes, blue seas, and even bluer skies. I recall the picturesque landscapes that no photo will ever be able to capture perfectly, as we journeyed from quiet villages to busy ports that are all distinctly Greek. With so many cool islands to explore, there is so much more to the Cyclades than Mykonos and Santorini where everyone congregates. This may be my favorite yacht charter to date.

Check out our post on How to Book a Yacht Charter for information on arranging a yacht charter in Greece.

antiparoscycladesgreecemykonosnaxosparosserifossifnossyrostravelyacht

Corissa Leung https://www.linkedin.com/in/corissaleung/