
Cyclades · Greece
Sail Cyclades.
Charter from Paros, Piso Livadi Port, Mykonos and Santorini — 62 yachts on the dock right now.
Why sail the Cyclades
The Cyclades are exposed, bright, and windier than most people expect. The islands sit in open Aegean water, so you feel the swell and the meltemi in a way you never do in the Ionian. That's the point. You get short, punchy passages between islands you can see from each other, water that runs deep blue over sand and pale turquoise over rock, and villages of white cube houses stacked above the harbour. It suits sailors who want to actually sail — trim the sails, watch the forecast, earn the anchorage. It suits it less if you want flat water and short hops with the engine on.
We've sailed these islands most summers. The reward is variety inside a small area: quiet fishing quays on Sifnos and Kythnos, the noise and buses of Mykonos, the caldera drama of Santorini, and Paros in the middle as a natural hub. You can build a week that mixes lively and empty as you please.
The sailing grounds and harbours
Paros is the practical centre. From here Naxos, Ios, Sifnos, Antiparos, Mykonos and Delos are all a day-sail away, and you rarely commit to a passage over 30 miles. Piso Livadi and Paroikia give you two departure points on the same island; Naoussa in the north is a working harbour worth a night.
Mykonos is busy, well-connected, and useful as a start or end point if guests are flying in tight. Ornos and Platys Gialos give shelter from the north when the town quay is full. Delos next door is a short hop and a genuine reason to go — day anchor only, no overnight.
Santorini is the outlier. Vlychada marina on the south coast is your base; the caldera itself has few real anchorages and deep water that drops away fast, so most people take a mooring buoy under the cliffs rather than anchor. It's stunning to look at and awkward to sail. Treat Santorini as a start or finish, not a cruising ground.
Season and winds — the meltemi, honestly
The season runs roughly May to October. July and August bring the meltemi: a dry north to north-west wind that builds through the afternoon and can hold Force 6 to 7 for days. It's a fair-weather gale — blue sky, big wind, short steep seas between the islands. Mornings are usually calmer, so we sail early and are anchored by early afternoon.
May, June, September and early October are gentler and, to our minds, better for most charters. You still get wind, but the multi-day meltemi is less likely and the harbours are quieter. If you want reliable strong wind for the sailing itself, come in high summer and plan short legs. If you want relaxed island-hopping, come in the shoulder months.
Plan north-to-south where you can, so the meltemi is behind you. Build slack days into the itinerary — being able to sit out a hard blow in a good harbour beats pushing into it on a schedule.
Charter types available
Most of what we run in the Cyclades is bareboat: you hold the qualifications, you skipper, you plan the week. A smaller number of yachts come crewed, with a skipper aboard who knows the meltemi and the anchorages — a sensible choice if it's your first Aegean charter or you'd rather not manage the wind yourself.
Bases spread across Paros, Mykonos and Santorini, so you can match your start point to your flights. One-way charters between islands are sometimes possible; ask us over WhatsApp and we'll tell you honestly what's on for your dates.
Realistic costs
Prices swing hard with boat size, age and season. A week on a mid-size bareboat monohull in the shoulder months costs less than the same boat in the first two weeks of August, when demand peaks. Catamarans run noticeably higher than monohulls of similar length. Beyond the base charter fee, budget for fuel, the end-of-charter clean, and mooring or marina fees on the nights you don't anchor — the Cyclades have more paid quays than the Ionian.
A skipper, if you want one, is an added daily rate. Because the numbers move so much by boat and date, we quote per enquiry rather than publish figures we can't stand behind — send us your dates and party size on WhatsApp and we'll come back with a real range. Price on request.
A sample week from Paros
Day 1 — board at Paros, provision in Paroikia, short sail to Naoussa for a first quiet night in the north.
Day 2 — cross to Mykonos with the wind on the beam; anchor at Ornos if the town is full, or take the quay early.
Day 3 — day-sail to Delos, anchor for the ruins, then on to Naxos for the evening under the Portara.
Day 4 — down the Naxos coast to a beach anchorage, a slower day to let the meltemi ease.
Day 5 — passage to Ios, lively harbour, good swimming on the way.
Day 6 — west to Sifnos, one of the better tavernas quays in the group, calmer water on the lee side.
Day 7 — work back north to Paros, timing the leg for the morning before the wind fills in. Adjust everything to the forecast — this is a sketch, not a rule.
Getting there and practical notes
Most people fly to Athens and take a fast ferry to Paros, Naxos or Mykonos, or fly direct to Mykonos or Santorini in season. Paros now has a small airport with domestic links from Athens. Ferries are frequent but sell out in August, so book them the moment your charter is confirmed.
Arrive the night before your charter if you can — a tired midnight arrival makes a poor first morning. Provisioning is straightforward in Paroikia, Naoussa and Mykonos town; smaller islands have less choice, so stock up before you leave the hub. Bring layers: the meltemi is cool at night and the spray is real. Message us on WhatsApp with your flights and we'll help line up the handover.
Live fleet
Yachts available in Cyclades.
62 yachts · page 1 of 2

Jacosta
Bareboat
Paros, Greece

Fortuna II
Bareboat
Piso Livadi Port, Greece

Maritina
Bareboat
Paros, Greece

Sky Star
Bareboat
Mykonos, Greece

Second Wind
Bareboat
Paros, Greece

Neda
Bareboat
Mykonos, Greece

Nereid
Bareboat
Mykonos, Greece

Kos 48.1
Bareboat
Mykonos, Greece

Kos 52.CAT3
Crewed
Mykonos, Greece

Blackberry
Bareboat
Paros, Greece

Blackberry
Bareboat
Paros, Greece

Simeon
Bareboat
Paros, Greece

H2O
Bareboat
Paros, Greece

Blue Moon II
Bareboat
Paros, Greece

Amigo
Bareboat
Paros, Greece

Danai
Bareboat
Mykonos, Greece

Hawaii 5-0
Bareboat
Paros, Greece

Little Blue Ocean
Bareboat
Paros, Greece

Argo I
Bareboat
Paros, Greece

Breezer
Bareboat
Mykonos, Greece

Olympia Athena
Bareboat
Mykonos, Greece

Greek Beauty'
Bareboat
Paros, Greece

Blue Argo
Bareboat
Paros, Greece

Almiriki
Bareboat
Paros, Greece

Blue Serenity
Bareboat
Paros, Greece

Red Rose
Bareboat
Mykonos, Greece

Amazing Elli
Bareboat
Piso Livadi Port, Greece

Butterfly
Bareboat
Paros, Greece

Rosa Dei Venti
Bareboat
Paros, Greece

Day One
Bareboat
Piso Livadi Port, Greece

Rosa Dei Venti
Bareboat
Paros, Greece

Olympios Zeus
Bareboat
Mykonos, Greece

Blue Trident
Bareboat
Mykonos, Greece

Wind Whisper
Bareboat
Paros, Greece

Eternity
Bareboat
Paros, Greece

Aktaia
Bareboat
Mykonos, Greece

Alas
Bareboat
Paros, Greece

Madicon
Bareboat
Santorini, Greece

Fo's
Bareboat
Mykonos, Greece

Kalisi Mou
Bareboat
Paros, Greece

Amalia
Bareboat
Piso Livadi Port, Greece

For Sail Too
Bareboat
Paros, Greece

Alpha
Bareboat
Mykonos, Greece

Wind of Change
Bareboat
Paros, Greece

Stefano
Bareboat
Paros, Greece

Naya
Bareboat
Paros, Greece

Elise
Bareboat
Paros, Greece

Elise
Bareboat
Paros, Greece
Cyclades questions
Asked and answered.
How much does a Cyclades yacht charter cost?
Do I need a licence to charter bareboat in the Cyclades?
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Should I choose a monohull or a catamaran?
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Bareboat or crewed in Cyclades?
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