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— Itinerary
Greece sailing routes

Cyclades yacht charter
itineraries.

Yacht charter in the Cyclades sailing area
— 20 routes

Pick your week from Cyclades.

Greece · Cyclades sailing area

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Yacht charter route: Athens – Mykonos – Paros
7-day loop
— Route 01 · From Athens
Athens → Mykonos → Paros → Athens

Sail a 7-day yacht charter from Athens via Kea, Syros & Mykonos to Paros. Explore iconic towns, hidden coves, island culture & Aegean magic.

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Yacht charter route: Athens – Kea – Syros – Hydra
7-day loop
— Route 02 · From Athens
Athens → Kea → Syros → Hydra → Athens

Sail a 7-day yacht charter from Athens via Cape Sounion, Kea, Syros, Serifos, Hydra and Poros — a hybrid Cyclades + Saronic loop with the most varied wind regimes of the route map.

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Yacht charter route: Athens – Mykonos – Santorini – Paros
14-day loop
— Route 03 · From Athens
Athens → Mykonos → Santorini → Paros → Athens

Sail a 14-day yacht charter from Athens (Alimos) through Mykonos and Santorini and back via Paros — the headline downwind Cyclades loop, planned for Meltemi-confident crews.

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Yacht charter route: Athens – Aegina – Hydra
7-day loop
— Route 04 · From Athens
Athens → Aegina → Hydra → Athens

Sail a 7-day yacht charter from Athens through the Saronic — Aegina, Poros, Spetses, Hydra and Agistri. Sheltered cruising ground for first-time bareboat or family crews.

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Yacht charter route: Athens – Aegina – Poros
7-day loop
— Route 05 · From Athens
Athens → Aegina → Poros → Athens

Sail a 7-day yacht charter from Athens through the Saronic — Aegina, Poros, Ermioni, Methana, Palaia Epidavros and Agistri. Mainland-side Saronic loop with archaeological focus.

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Yacht charter route: Athens – Monemvasia – Nafplio
14-day loop
— Route 06 · From Athens
Athens → Monemvasia → Nafplio → Athens

Sail a 14-day yacht charter from Athens through the Saronic and the Argolic Gulf to Monemvasia and back via Hydra. Mainland Peloponnese cruising for archaeology + quiet anchorages.

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Yacht charter route: Paros – Syros – Milos – Ios
14-day loop
— Route 07 · From Paros
Paros → Syros → Milos → Ios → Paros

Sail a 14-day yacht charter round-trip from Paros via Sifnos, Serifos, Kythnos, Syros, Mykonos, Naxos, Ios, Santorini, Folegandros and Milos. Full grand-tour Cyclades.

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Yacht charter route: Paros – Milos – Santorini – Syros
14-day loop
— Route 08 · From Paros
Paros → Milos → Santorini → Syros → Paros

Sail a 14-day yacht charter from Paros via Naxos, Donousa, Amorgos, Small Cyclades, Santorini, Milos, Sifnos, Kythnos and Syros. Cyclades grand tour from Paros base.

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Yacht charter route: Santorini – Mykonos – Milos
14-day loop
— Route 09 · From Santorini
Santorini → Mykonos → Milos → Santorini

Sail a 14-day yacht charter round-trip from Santorini through Mykonos, Amorgos, Naxos and Milos. Vlychada start avoids the Athens crossing — straight into the southern Cyclades.

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Yacht charter route: Paros – Ios – Santorini
7-day loop
— Route 10 · From Paros
Paros → Ios → Santorini → Paros

Sail a 7-day yacht charter from Paros via Ios and Santorini, returning through Folegandros and Sifnos. Compact southern Cyclades loop for confident-Meltemi crews.

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Yacht charter route: Paros – Naxos – Schoinousa
7-day loop
— Route 11 · From Paros
Paros → Naxos → Schoinousa → Paros

Sail a 7-day yacht charter from Paros via Naxos, Donousa, Koufonissi, Schoinousa and Irakleia. Central + Small Cyclades loop with the quietest anchorages on the Aegean charter map.

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Yacht charter route: Paros – Syros – Mykonos
7-day loop
— Route 12 · From Paros
Paros → Syros → Mykonos → Paros

Sail a 7-day yacht charter from Paros via Sifnos, Syros, Tinos and Mykonos. Northern Cyclades loop covering the marble-carving capital, neoclassical Ermoupoli and Mykonos.

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Yacht charter route: Santorini – Milos – Paros
7-day loop
— Route 13 · From Santorini
Santorini → Milos → Paros → Santorini

Sail a 7-day yacht charter from Santorini through Ios, Paros, Serifos, Sifnos and Milos and back. Southern + western Cyclades loop combining caldera + lunar volcanic islands.

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Yacht charter route: Lavrion – Milos – Sifnos
14-day loop
— Route 14 · From Lavrion
Lavrion → Milos → Sifnos → Lavrion

Sail a 14-day yacht charter from Lavrion through Andros, Tinos, Donousa, Amorgos, Koufonissi, Folegandros and back via Milos and Sifnos. Full Cyclades grand tour.

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Yacht charter route: Lavrion – Mykonos – Santorini
14-day loop
— Route 15 · From Lavrion
Lavrion → Mykonos → Santorini → Lavrion

Sail a 14-day yacht charter from Lavrion through Syros, Tinos, Mykonos and Santorini and back. Lavrion start saves the Saronic crossing — the central Cyclades on minimum motoring.

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Yacht charter route: Mykonos – Naxos – Paros – Kea
14-day loop
— Route 16 · From Mykonos
Mykonos → Naxos → Paros → Kea → Mykonos

Sail a 14-day yacht charter from Mykonos through Naxos, Paros, Milos, Sifnos, Serifos, Kythnos, Kea, Andros, Tinos and Syros — the full central + western Cyclades grand tour.

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Yacht charter route: Lavrion – Kea – Kythnos – Sifnos
7-day loop
— Route 17 · From Lavrion
Lavrion → Kea → Kythnos → Sifnos → Lavrion

Sail a 7-day yacht charter from Lavrion through Kea, Kythnos and Sifnos with Serifos on the return. Compact western Cyclades loop suitable for shoulder-season Meltemi.

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Yacht charter route: Lavrion – Mykonos – Paros
7-day loop
— Route 18 · From Lavrion
Lavrion → Mykonos → Paros → Lavrion

Sail from Lavrion via Mykonos to Paros on a yacht charter. Discover iconic nightlife, hidden coves, blue domes & the timeless charm of the Cyclades.

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Yacht charter route: Mykonos – Kea – Syros
7-day loop
— Route 19 · From Mykonos
Mykonos → Kea → Syros → Mykonos

Sail a 7-day yacht charter from Mykonos via Tinos, Andros, Kea, Kythnos and Syros — northern Cyclades loop covering the marble-carving capital and the neoclassical Ermoupoli.

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Yacht charter route: Mykonos – Naxos – Paros
7-day loop
— Route 20 · From Mykonos
Mykonos → Naxos → Paros → Mykonos

Sail a 7-day yacht charter from Mykonos via Naxos and Paros, returning through Sifnos, Serifos and Syros — central Cyclades downwind loop with Meltemi-confident sailing.

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— About Cyclades

Cyclades, in the broker's words.

The Cyclades are the most demanding charter ground in Greece — and the most photogenic. Bases at Athens (Alimos, Kalamaki, Lavrion) put you 30–45 NM from Kea on the first leg, and from there the meltemi (typically 4–6 Bft, peaking 7+ in late July/August) drives a southward arc through Kythnos, Serifos, Sifnos, Paros, Mykonos, Santorini and Ios. Charters that try to claw back north against the meltemi without time and patience get expensive in fuel and uncomfortable in passages — the conventional one-way drop in Paros or Mykonos solves both.

Vessel mix in the Cyclades runs heavy on monohull sailing yachts (45–55 ft) because they handle the meltemi better than catamarans on close-reach upwind legs. Catamarans excel for crews staying in the more-protected southern Cyclades cluster (Sifnos, Folegandros, Milos) where the wind angle is mostly downwind. Motor yachts and crewed luxury yachts dominate the Mykonos–Santorini party charter market.

Best season is May–June and September — meltemi blows lighter, town anchorages are uncrowded, water temperature stays swimmable, and prices drop 30–40% vs August peak. The Cyclades reward experienced skippers; first-time bareboaters typically pick the gentler Ionian first.

— Plan your week

Like one of these routes? We'll tailor it.

Send your dates, departure base and crew size. A broker replies with a route built around your group and matching yachts — usually within the same business day.

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