Greece Sailing Itinerary: 7 Days Through the Cyclades Islands

The Greek islands are a must-visit destination for any traveler. Indeed, the Greek islands have topped countless lists as a top destination around the world. In this itinerary, we lay out for you a plan to go from Athens to Mykonos and see the most spectacular highlights the Greek islands have to offer.

1st DAY:  Athens Riviera to Cape Sounion

The Athens Riviera is a coastal area in the southernmost suburbs of Athens. On this sailing route, you will find the most cosmopolitan beaches of Athens, including Alimos, Glyfada, Vouliagmeni, Lagonissi and Varkiza.

Cape Sounion is located 69 kilometers (43 miles) southeast of Athens, at the southernmost tip of the Attica peninsula in Greece. Recently, the wider region of Cape Sounion was declared a national park, and is now protected by the Greek government. Cape Sounion is also home to the ruins of the ancient Greek temple of Poseidon, the god of the sea in classical Greek mythology. From the ruins, one can view the sunset over the Aegean Sea, a famous and beautiful view that many travel to see.

2nd DAY:  Kythnos to Syros

Kythnos, located in the Western part of the Cyclades, has perhaps the most beautiful beach out of all the Greek islands. This beach, a crescent- shaped isthmus, has extremely fine sand and warm thermal springs at Loutra bay, which are told to have healing properties.

Kythnos also has picturesque villages with cobblestone streets and white houses with blooming flower courtyards. Kythnos is warm, friendly, and simple. Walk through its quiet neighborhoods and dine on fresh food at waterfront tables.

Syros is located 144 kilometers (78 miles) southeast of Athens. Its capital, Ermoupoli, is a neoclassical town and one of the most beautiful settlements you will encounter in the Cyclades. Syros’s Roman quarter is home to the fortress-like St. George’s Cathedral. Go up to the top of the hill the Cathedral sits on, through the narrow streets, past the traditional whitewashed houses, and through the archways and open spaces to catch a breathtaking view of the entire island.

Syros also has beautiful architecture, such as the churches of St. Nicolas the Rich and Dormition of the Mother of God.  On the hill that St. George’s Cathedral sits on, also sits the remarkable medieval settlement of Ano Syros, built during 300 AD.

3rd DAY: MYKONOS  

The most famous island of the Aegean, Mykonos is bright and cosmopolitan, with exciting nightlife and stunning scenery. With its stunning beaches, award-winning restaurants, endless fantastical parties, and dream villas, it is no wonder Mykonos has been voted one of the top vacation destinations worldwide.

If the Mykonos nightlife scene isn’t for you, don’t worry. Mykonos is also home to the Ano Mera Village, a calm, authentic, and picturesque town home to the historic church Panagia Tourliani as its main attraction.

A very diverse island, Mykonos has become the most gay-friendly destination in Greece and the most popular in the world.

Mykonos is also home to Little Venice, and its houses (which were built in the 18th century) have foundations in the sea! Today they offer bars, restaurants, and stunning views of the Aegean from their balconies.

The other trademark of Mykonos are the Kato Myloi, a series of windmills, that, built by the Venetians in the 16th century, milled flour up until the mid-1900’s. Today, they are home to locals and serve as vaults to numerous Mykonian heritage documents.

Moreover, Mykonos has tons of scuba diving, and its waters are home to some amazing creatures, including octopus, starfish, and Mediterranean monk seals! There are countless companies which offer diving expeditions through reefs, caves, and even shipwrecks!

4th DAY: MYKONOS – DELOS & RHENIA ISLANDS

Delos is one of the most important mythological, historical, and archaeological sites in Greece. Dolos is the birthplace of the twin gods Apollo and Artemis and has been a holy sanctuary for a millennium. Admire beautiful archaeological sites and watch the unique sunset on the island of the god of light, Apollo.

Charter your boat in Rinia, where you can dive into blue waters and cool off in the fresh air. Rinia is a peaceful, almost deserted island where one can recharge and catch a break from all the noise.

5th DAY: NAXOS or KOUFONISIA

Naxos is the largest, most fertile, and self-sufficient island of the Cyclades. In the harbor, one is welcomed by Portara, a large marble frame and an ancient Apollo Temple, along with a view of a medieval castle. The island has a history dating back centuries, unique sights, varying landscapes, and delicious food.

A visit to Naxos is not complete without the exploration of the picturesque countryside and the mountain villages of the island which have been inhabited for centuries.

Naxos was rated the sixth best island in the world and the number two place to visit in Europe according to TripAdvisor, the popular travel site’s, users. It is also described as a critical culinary destination because it produces some of Greece’s most famous exports including many Greek cheeses.

Koufonissia is a well-hidden terrestrial paradise that is also definitely worth visiting. Filled with quiet beaches and caves, Koufonissia is an excellent place for relaxation and time to oneself.

Koufonissia, with its crystal clear waters, has plenty of opportunities for beautiful Mediterranean diving. With dreamy landscapes and tranquil music, Koufonissia is one of the most peaceful places to explore.

6th DAY: PAROS or SIFNOS

Paros also has beaches with crystal clear waters and magnificent beauty Also in Paros however, you’ll discover Byzantine footpaths which which connect traditional villages like Naoussa, a colorful village where the ruins of a Venetian fortress stand at the entrance to its small harbor. Naoussa is also home to exquisite shopping opportunities in the town’s narrow alleyways and fine dining along its shores.

Sifnos combines picturesque views with folk art and tradition. It has many medieval remains and contains 360 churches, for the number of days in a year.

Sifnos is an island famous for its architecture and its beauty. Elegant but simple at the same time, Sifnos is full of stunning, pure beauty.

7th DAY : SERIFOS to ATHENS

Serifos is the ideal place for taking a stroll or stopping into one of its cafes, fish taverns, or pastry shops located next to the sea. Chora, Serifos’s capital city, was built on a rocky hilltop overlooking over the rest of the island, and houses a Venetian castle built in the 15th century. The most beautiful architectural building on Serifos however, is the ancient Hellenistic marble watchtower Aspros Pirgos, or “White Tower.”

Simply put, Serifos has beautiful, simple Cycladic architecture that has remained unchanged for centuries.

With magnificent views, archaeological wonders, and fantastic adventures, you’re sure to love this itinerary which takes sailors to all of the must-see Greek islands.

Enjoy!

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