Sailaway Charters
Cyclades, Greece sailing area

Cyclades · Greece

Sail Cyclades.

Charter from Paros, Piso Livadi Port, Mykonos and Santorini — 62 yachts on the dock right now.

See yachts in CycladesTalk to an expert
62 yachts60 bareboat

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.

Live fleet

Yachts available in Cyclades.

62 yachts · page 1 of 2

Jacosta

Jacosta

Bareboat

Paros, Greece

10 berths4 cabins15 mSailing Yacht · 2012
from
€2,800
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Fortuna II

Fortuna II

Bareboat

Piso Livadi Port, Greece

10 berths4 cabins12 mCatamaran · 2020
from
€3,880
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Maritina

Maritina

Bareboat

Paros, Greece

10 berths4 cabins14 mCatamaran · 2023
from
€4,250
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Sky Star

Sky Star

Bareboat

Mykonos, Greece

10 berths4 cabins14 mCatamaran · 2023
price on enquiry
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Second Wind

Second Wind

Bareboat

Paros, Greece

12 berths4 cabins14 mCatamaran · 2022
from
€5,150
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Neda

Neda

Bareboat

Mykonos, Greece

11 berths5 cabins14 mCatamaran · 2024
from
€5,150
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Nereid

Nereid

Bareboat

Mykonos, Greece

11 berths5 cabins15 mCatamaran · 2025
from
€5,450
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Kos 48.1

Kos 48.1

Bareboat

Mykonos, Greece

12 berths6 cabins15 mCatamaran · 2020
from
€3,800
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Kos 52.CAT3

Kos 52.CAT3

Crewed

Mykonos, Greece

14 berths6 cabins16 mCatamaran · 2026
from
€9,850
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Blackberry

Blackberry

Bareboat

Paros, Greece

8 berths3 cabins12 mSailing Yacht · 2025
from
€2,010
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Blackberry

Blackberry

Bareboat

Paros, Greece

8 berths3 cabins12 mSailing Yacht · 2025
from
€3,343
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Simeon

Simeon

Bareboat

Paros, Greece

12 berths5 cabins14 mSailing Yacht · 2019
from
€2,020
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H2O

H2O

Bareboat

Paros, Greece

9 berths4 cabins14 mSailing Yacht · 2017
from
€1,925
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Blue Moon II

Blue Moon II

Bareboat

Paros, Greece

8 berths4 cabins13 mSailing Yacht · 2020
from
€2,100
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Amigo

Amigo

Bareboat

Paros, Greece

10 berths4 cabins14 mSailing Yacht · 2020
from
€2,430
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Danai

Danai

Bareboat

Mykonos, Greece

12 berths5 cabins15 mCatamaran · 2023
from
€5,200
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Hawaii 5-0

Hawaii 5-0

Bareboat

Paros, Greece

12 berths5 cabins15 mCatamaran · 2024
from
€5,200
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Little Blue Ocean

Little Blue Ocean

Bareboat

Paros, Greece

10 berths4 cabins11 mCatamaran · 2025
from
€2,800
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Argo I

Argo I

Bareboat

Paros, Greece

12 berths4 cabins13 mCatamaran · 2023
from
€4,250
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Breezer

Breezer

Bareboat

Mykonos, Greece

12 berths6 cabins16 mCatamaran · 2024
from
€8,000
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Olympia Athena

Olympia Athena

Bareboat

Mykonos, Greece

11 berths4 cabins13 mCatamaran · 2023
from
€4,500
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Greek Beauty'

Greek Beauty'

Bareboat

Paros, Greece

12 berths4 cabins13 mCatamaran · 2020
from
€4,500
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Blue Argo

Blue Argo

Bareboat

Paros, Greece

10 berths4 cabins13 mCatamaran · 2026
from
€4,800
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Almiriki

Almiriki

Bareboat

Paros, Greece

10 berths4 cabins12 mCatamaran · 2023
from
€3,000
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Blue Serenity

Blue Serenity

Bareboat

Paros, Greece

10 berths4 cabins12 mCatamaran · 2022
from
€3,750
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Red Rose

Red Rose

Bareboat

Mykonos, Greece

11 berths5 cabins14 mCatamaran · 2018
from
€4,250
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Amazing Elli

Amazing Elli

Bareboat

Piso Livadi Port, Greece

14 berths5 cabins16 mSailing Yacht · 2018
from
€4,450
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Butterfly

Butterfly

Bareboat

Paros, Greece

10 berths4 cabins12 mCatamaran · 2019
from
€2,270
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Rosa Dei Venti

Rosa Dei Venti

Bareboat

Paros, Greece

9 berths4 cabins13 mCatamaran · 2021
from
€5,100
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Day One

Day One

Bareboat

Piso Livadi Port, Greece

11 berths4 cabins13 mCatamaran · 2020
from
€4,200
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Rosa Dei Venti

Rosa Dei Venti

Bareboat

Paros, Greece

9 berths4 cabins13 mCatamaran · 2021
from
€5,100
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Olympios Zeus

Olympios Zeus

Bareboat

Mykonos, Greece

12 berths4 cabins13 mCatamaran · 2019
from
€3,800
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Blue Trident

Blue Trident

Bareboat

Mykonos, Greece

12 berths4 cabins13 mCatamaran · 2019
from
€3,800
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Wind Whisper

Wind Whisper

Bareboat

Paros, Greece

10 berths4 cabins13 mCatamaran · 2020
from
€3,500
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Eternity

Eternity

Bareboat

Paros, Greece

10 berths4 cabins13 mCatamaran · 2023
from
€3,800
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Aktaia

Aktaia

Bareboat

Mykonos, Greece

10 berths4 cabins13 mCatamaran · 2020
from
€4,100
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Alas

Alas

Bareboat

Paros, Greece

10 berths4 cabins13 mCatamaran · 2020
from
€3,800
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Madicon

Madicon

Bareboat

Santorini, Greece

10 berths4 cabins14 mCatamaran · 2019
from
€4,500
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Fo's

Fo's

Bareboat

Mykonos, Greece

12 berths4 cabins14 mCatamaran · 2020
from
€4,500
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Kalisi Mou

Kalisi Mou

Bareboat

Paros, Greece

10 berths4 cabins14 mCatamaran · 2021
from
€5,160
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Amalia

Amalia

Bareboat

Piso Livadi Port, Greece

12 berths4 cabins14 mCatamaran · 2024
from
€5,750
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For Sail Too

For Sail Too

Bareboat

Paros, Greece

12 berths6 cabins15 mCatamaran · 2018
from
€5,300
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Alpha

Alpha

Bareboat

Mykonos, Greece

13 berths6 cabins15 mCatamaran · 2026
from
€8,000
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Wind of Change

Wind of Change

Bareboat

Paros, Greece

8 berths3 cabins11 mSailing Yacht · 2010
from
€1,300
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Stefano

Stefano

Bareboat

Paros, Greece

10 berths4 cabins13 mSailing Yacht · 2025
from
€1,900
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Naya

Naya

Bareboat

Paros, Greece

10 berths4 cabins14 mSailing Yacht · 2014
from
€1,960
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Elise

Elise

Bareboat

Paros, Greece

13 berths5 cabins16 mSailing Yacht · 2020
from
€4,550
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Elise

Elise

Bareboat

Paros, Greece

12 berths5 cabins16 mSailing Yacht · 2020
from
€4,900
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Cyclades questions

Asked and answered.

How much does a Cyclades yacht charter cost?
It depends heavily on boat size, age, type and season. A mid-size bareboat monohull costs less in May, June, September and October than in the first fortnight of August. Catamarans run higher than monohulls. On top of the base fee, budget for fuel, the end clean, and quay or marina fees. Because prices move so much, we quote per enquiry — send dates and party size on WhatsApp. Price on request.
Do I need a licence to charter bareboat in the Cyclades?
Yes. For a bareboat you'll normally need a recognised sailing qualification such as an ICC or RYA Day Skipper, plus a second competent crew member, and often a VHF certificate. Requirements can vary, so tell us what you hold when you enquire. If you don't have the paperwork or the confidence for the meltemi, take a crewed yacht with a skipper aboard instead.
When is the best time to sail the Cyclades?
May, June, September and early October are the sweet spots: enough wind to sail, quieter harbours, and less chance of a multi-day meltemi. July and August bring the strongest, most reliable wind — Force 6 to 7 is common — which suits confident sailors who want the challenge and don't mind busy quays. Sail mornings in high summer and be anchored by afternoon.
Where should I start my charter?
Paros is the most practical base — central, well-connected by ferry and its own airport, with day-sails to Naxos, Mykonos, Delos, Ios and Sifnos. Mykonos works if guests fly in on tight schedules. Santorini is best as a start or finish only, since the caldera has few real anchorages. Match your base to your flights and message us to confirm what's available on your dates.
Is the Cyclades good for families with children?
It can be, in the shoulder months. In May, June and September the wind is gentler and the water calm enough for easy swimming and short hops. High-summer meltemi brings big wind and steep seas that are hard work with small children aboard. If you're sailing with kids, come outside peak August, keep legs short, and consider a skipper so you're free to look after the crew.
Should I choose a monohull or a catamaran?
Catamarans give more deck space, shallower draught for beach anchorages, and steadier motion at anchor — good for families and less experienced crews. Monohulls sail better upwind against the meltemi, cost less, and slip into tighter quays. In strong Cyclades wind a monohull is more forgiving to sail; a catamaran is more comfortable to live on. Tell us your priorities and we'll point you to the right boats.
How many yachts can I charter in Cyclades?
Right now there are 62 active yachts in Cyclades, based out of Paros, Piso Livadi Port, Mykonos and Santorini. The fleet list above is live from our operator system.
Bareboat or crewed in Cyclades?
60 of the boats here are bareboat, 2 come crewed. Tell us your experience level and we'll match you.
How do I get a quote?
Send us your dates, your group and roughly the boat you want. Same day, we reply with three real options, three prices and the honest trade-offs.
Talk to a real charter expert

Real people

Talk to a human

A real person reads every message and replies within 24 hours — no bots, no auto-replies.

  • Honest advice from sailors, not salespeople
  • We reply within 24 hours
  • No spam, ever

Talk to an expert

Get three options.

Real sailors who run the trips — tell us your week, your group and your vibe. Same day, we send three boats, three prices and the honest trade-offs. Boats we would put our own families on.

Real humans on every channel — WhatsApp, email, phone. No call centre.

Final boarding call

Why not you?

New sailors, beginners or seasoned skippers — tell us when, where and how many. We send three real options the same day. No spam, no fluff, no commitment.

60 seconds. No payment until you choose a boat.
Yacht under sail at sunset

Free quote

Get three real options.

Tell us roughly when and where. We'll send three real boats, three prices, the trade-offs — usually within the hour.