For a traveler, there is nothing quite like exploring the Cyclades by sailboat, where one can immerse themselves among islands adorned with beautiful beaches, archaeological sites and secluded villages with an authentic and relaxed ambiance.

Greece, nestled in the Mediterranean with its thousands of islands swept by the Meltemi winds, has always been an ideal destination for those visiting by sailboat. This mode of travel allows not only for the discovery of its ancient culture but also for a leisurely exploration of its stunning coastlines, harbors, remote villages, and to breathe in their genuine atmosphere. Among the approximately 6,000 islands available for landing, we suggest an itinerary in one of the most beloved archipelagos by sailors: the Cycladic Islands.

The Cyclades are a cluster of over 200 islands situated in the Aegean Sea, named for their circular arrangement around the island of Delos. Only a few of these islands are inhabited and even fewer are well-known to tourists. The infamous Meltemi wind, a strong force especially in July and August, sweeps through this archipelago, bringing joy to sailors. Spending a few days sailing here will take you back to traditional Greece. Whether in Paros, Naxos, or Mykonos, you’ll breathe in the glory of their splendid past, with quaint fishing ports and the irresistible charm of the Mediterranean lifestyle.

Day 1, Embarking at Paros

Your sailing trip begins in the bay of Parikia on the western side of Paros. This is where you’ll find the island’s namesake capital, a captivating town with a labyrinthine historic center bustling with shops, cafés, and restaurants. It’s also home to a busy port with ferries to other islands and a charming waterfront that comes alive in the evenings, surrounded by beautiful sandy beaches. Parikia is an ideal base for comfortably exploring the island and a recommended spot for nightlife enthusiasts.

Once settled on board, you can choose to dive into the island’s classical culture by visiting its small but fascinating museums, explore the traditional villages inland, join the legendary beach parties at Pounda, or simply enjoy the picturesque beaches of the island.

Day 2, Paros to Sifnos, 23 Miles

Departing from the docks of Paros, we set sail westward towards Sifnos for a 23-mile voyage. The southern tip of the island provides good shelter from the Meltemi wind in Plati Yialos Bay. Alternatively, one can head further northwest to the sheltered bay of Vathi, which is dotted with small taverns. There’s only a small dock for mooring here, or you can anchor and use a dinghy. The main town is Kamares, located a bit further north, boasting a wide variety of shops.

The island of Sifnos is known for its cobblestone streets, seafront chapels, and dramatic cliff peaks. Historically recognized for its significant marble deposits, as well as gold and silver mines, the island’s mines and quarries are no longer active, leaving only ruins scattered across the landscape. The island’s pottery is also highly renowned, particularly in the settlement of Kamares, where numerous esteemed workshops can be found. Beyond this, there are incredible beaches, scenic trails, and an interior landscape of breathtaking beauty.

Day 3, Sifnos to Serifos, 11 Miles

From Kamares in Sifnos, the island of Serifos is a mere 10 miles away. This small, tranquil island never fails to impress visitors with its wild nature, non-touristy ambiance, and natural beauty. This includes its secluded beaches, which remain uncrowded even during peak season. A good landing spot is the seaside village of Livadi. The village port is situated in a large bay on the island’s eastern coast. Caution is advised during the Meltemi winds due to strong gusts descending from the mountains, though the waves are typically small. Alternatively, you can anchor offshore, as many yachts do, and use a dinghy to go ashore.

The island’s main village, Chora, is perched atop the mountains, boasting stunning views from the church at its peak. Chora also features a couple of small museums and many quaint cafés perfect for a quick ‘tsipouro’ or a cold beer. Small restaurants serve delicious food, and there are wonderful bars for enjoying music and drinks under the stars. To get to Chora, take a local bus or taxi from Livadi port; the journey takes just 10-15 minutes.

Day 4, Serifos to Syros, 21 Miles

After spending the night in Serifos, it’s time to set sail towards Syros, approximately 20 miles away. Once there, you have the option of docking at Finikas on the western side of the island, or for a slightly longer journey, heading to Ermoupoli, the capital of the Cycladic Islands. Ermoupoli is bustling with shops, restaurants, and the feel of a larger city. Care should be taken when entering the harbor as it can be busy due to the local shipyard.

Ermoupolis, the capital of Syros, is a beautiful city worth exploring. It boasts a collection of ancient Orthodox and Catholic churches and a labyrinth of small streets with sea views. The city is also home to a famous casino for those interested in such entertainment. Finikas Marina, on the other hand, offers a more intimate and relaxed atmosphere with all the necessary amenities.

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Day 5, Syros to Mykonos, 17 Miles

Approximately 17 miles east of Syros lies Mykonos, centrally located in the Cyclades. Over the years, Mykonos has become one of the Mediterranean’s most popular destinations, known for its vibrant nightlife and beautiful beaches. But it’s also known as the “island of the windmills,” and its winding narrow streets, white houses with colorful windows, flower-decked balconies, and excellent traditional cuisine will captivate you. Enjoy the sun and sand at Paradise Beach, a hotspot among sailors.

Away from the beach, take a trip to Chora to explore the Panagia Paraportiani church. Chora is renowned as one of the island’s most picturesque areas. There’s a new marina located a bit outside the town, offering more facilities than the old dock in the main town. Various anchorages are available around the southern side of the island, and the small bays on the nearby islands of Rinia and Delos are also worth a visit.

Day 6, Mykonos to Delos to Naxos, 21 Miles

On the sixth day of our voyage, a swift sail under the influence of the Meltemi winds takes us to Delos. A legendary birthplace of Apollo and Artemis, as well as a popular archaeological site, this landmass is steeped in Greek mythology. It’s considered a sacred place, and anchoring overnight on this island is prohibited. However, we can anchor in the bay of Rinia to enjoy swims and excursions ashore. A complete tour of Delos takes several hours, but these hours are rewarding, leaving lasting impressions of this unique island. The island’s archaeological museum houses one of the finest collections of ancient Greek sculptures.

We then continue sailing towards Naxos, the largest and greenest island of the Cyclades. The eponymous town, with its recently revamped and welcoming main harbor promenade, is perfect for a pleasant evening exploring the city. This is where we will stay. With its towering mountains, fertile lands, pristine beaches, and spectacular Aegean views, Naxos is a visual paradise. Its inhabitants still wear traditional clothing and live off the land’s harvests.

The island is also dotted with ancient chapels, monasteries, and Venetian castles, echoing its centuries-old history. Naxos is renowned for its cultural events and traditional festivals, such as the Naxos Festival, the Wine Festival, and the Fisherman’s Feast, allowing you to immerse yourself in the rich folk culture of this slice of Greece surrounded by the sea. Or, step back in time as you wander through the winding streets of the old town. You’ll be utterly enchanted.

Day 7, Naxos to Paros, 15 Miles

On the final day of our cruise, we embark on a short 15-mile journey back to the port of Parikia on the island of Paros. Depending on the time you have left, you can sail into the beautiful Naoussa Bay on the island’s north side, or perhaps enjoy a swim at one of the sandy beaches or visit the town of Naoussa with its traditional fishing port and restaurants. The real trouble with this trip is that one never wants to leave the Cyclades!