Greece (Cyclades)

Island Hopping in the Aegean

€2,000/week

Overview

The Cyclades archipelago is the quintessential Greek sailing experience. Over 30 islands form a rough circle in the central Aegean Sea, each one a postcard of whitewashed villages, blue-domed churches, and rugged hillsides dropping into deep cobalt waters. From the cosmopolitan nightlife of Mykonos to the quiet marble quarries of Naxos, the Cyclades reward sailors with extraordinary variety within short passages that rarely exceed 20 nautical miles. Sailing here means contending with the Meltemi, the famous northerly wind that blows across the Aegean from June through September. On moderate days the Meltemi delivers exhilarating broad reaches and beam-on sailing; on stronger days it can push above 30 knots and demands respect. Experienced sailors relish the challenge, while those on skippered charters can sit back and enjoy the ride. Anchorages tend to be deep and open, so a good understanding of anchor technique and weather routing is essential for bareboat crews. Beyond the sailing, the Cyclades offer an immersion in history and gastronomy that few destinations can match. Delos, the mythological birthplace of Apollo, is an open-air archaeological museum. Syros features a grand neoclassical capital with Venetian and Orthodox heritage side by side. Every island serves fresh grilled octopus, local cheeses, and carafes of house wine at harbourfront tavernas where the pace of life slows to match the rhythm of the tides.

Highlights

Sail past the iconic windmills and white-cube architecture of Mykonos town at golden hour
Anchor in the volcanic caldera of Santorini for a sunset dinner with views of Oia's cliffside terraces
Explore the ancient ruins of Delos, a UNESCO World Heritage Site accessible only by boat
Wander the marble-paved alleys of Parikia and Naoussa on Paros, stopping for local wine and mezze
Swim in the crystal-clear waters of Koufonisia, a tiny island with some of the Aegean's best beaches
Experience the authentic Venetian-era capital of Ermoupoli on Syros, the administrative heart of the Cyclades

Sample Itineraries

Cyclades Explorer: Athens to the Islands

7 days

Athens/Lavrion to Kea

Depart from Lavrion Marina on the Attic Peninsula, just an hour from Athens International Airport. The 15-nautical-mile crossing to Kea is an easy introduction to Aegean sailing. Arrive at the picturesque harbour of Korissia and explore the hilltop village of Ioulis, with its famous stone lion carved in the 6th century BC. Dine at a traditional taverna overlooking the bay.

Korissia, KeaAncient Lion of Kea and hilltop village of Ioulis

Kea to Syros

Sail northwest to Syros, capital of the Cyclades. The 25-mile passage typically runs on a beam reach with the prevailing northerlies. Ermoupoli is a grand neoclassical port town with the ornate Apollo Theatre, a miniature La Scala. Climb to Ano Syros for panoramic views and a Venetian Catholic quarter with narrow medieval lanes.

Ermoupoli Harbour, SyrosErmoupoli's neoclassical architecture and Apollo Theatre

Syros to Mykonos

A short 18-mile sail east delivers you to Mykonos, one of the most famous islands in Greece. Arrive early to secure a spot in the old harbour or use the new marina at Tourlos. Walk through the labyrinthine streets of Mykonos Town, past the iconic Paraportiani Church and the row of 16th-century windmills. Little Venice offers cocktails at sunset right at the water's edge.

Mykonos Town / Tourlos MarinaLittle Venice sunset and the windmills of Mykonos

Mykonos to Paros

Head south on a broad reach to Paros, arriving at the charming fishing village of Naoussa. The harbour is ringed with seafood restaurants and boutique shops. In the afternoon, visit the Frankish castle ruins at the entrance of the port or hire a scooter to explore the island's interior, with its marble quarries and Byzantine trail network.

Naoussa, ParosNaoussa fishing harbour and seafood tavernas

Paros to Naxos

The crossing to Naxos is one of the shortest of the trip at just 8 miles. Naxos Town is dominated by the Portara, the massive marble doorway of an unfinished Temple of Apollo that frames spectacular sunsets. The island is the largest and most fertile in the Cyclades, known for its potatoes, cheese, and kitron liqueur. Explore the old Venetian kastro quarter above the harbour.

Naxos Town HarbourSunset at the Portara, Temple of Apollo gateway

Naxos to Kythnos

Begin the return leg with a sail northwest toward Kythnos, a quiet island with natural hot springs and empty beaches. The passage of roughly 35 miles can be broken with a lunch stop at a sheltered cove. Anchor in the double bay of Kolona, a sandy isthmus connecting two headlands, and enjoy a swim in the warm, shallow waters before a final evening aboard.

Kolona Bay, KythnosSwimming at Kolona's unique double beach

Kythnos to Lavrion

The final morning sail back to Lavrion covers about 20 nautical miles. Arrive by midday for a smooth charter return and checkout. If your flight is in the evening, take time for a farewell lunch at one of the excellent fish restaurants in the Lavrion harbour before transferring to Athens Airport.

Lavrion Marina, AthensFarewell lunch at Lavrion harbour

Practical Information

Getting There

Athens International Airport (ATH) is the main gateway, served by direct flights from across Europe, North America, and the Middle East. Lavrion Marina is approximately 60 kilometres (45 minutes by car) southeast of the airport. Alternatively, charters can begin from Alimos Marina near central Athens. Domestic ferries and flights connect most Cycladic islands to Piraeus and Rafina.

Athens International Airport (ATH)

Mykonos Airport (JMK)

Santorini Airport (JTR)

Marinas

Lavrion Olympic Marina -- Lavrion, Attica
Alimos Marina (Kalamaki) -- Athens, Attica
Tourlos Marina -- Mykonos

Weather

Summer in the Cyclades is hot and dry with temperatures reaching 30-35 °C. The Meltemi wind blows from the north between June and September, with the strongest periods in July and August when sustained speeds of 25-30 knots are common. Spring (May-June) and autumn (September-October) offer lighter winds and fewer crowds. Winter sailing is not recommended due to unpredictable weather and limited services.

Provisioning

Major provisioning should be done at supermarkets near Lavrion or Alimos before departure. AB Vassilopoulos and Sklavenitis are the largest chains. Once in the Cyclades, each island has mini-markets with basics, and fresh produce, meat, and seafood are available at local markets in Mykonos, Paros, and Naxos. Water and fuel are available at most island ports, though it can be expensive.