Made up of around 220 islands and islets in the heart of the Aegean Sea, the Cyclades archipelago is the go-to destination for a sailing or catamaran cruise in Greece. A Cyclades cruise costs from around €1,650 per person (8 days / 7 nights), with the option to sail with a skipper, without a skipper, with a crew or by cabin. If you want to hire a sailing boat in the Cyclades, you will sail between Santorini, Mykonos, Paros and Naxos, taking in whitewashed villages, crystal-clear waters and anchorages reachable only from the sea, an ideal setting for families and groups of friends.
The types of boat to hire in the Cyclades
In the Cyclades you sail at sea: the choice of boat depends on your crew, your experience and the level of comfort you are after.
- The monohull sailing boat: the most common and most affordable option for a sailing cruise, perfect for experiencing navigation up close on the Aegean Sea. Discover our boats to arrange a sailboat charter, with or without a skipper.
- The catamaran: more stable, more spacious and brighter, recommended for groups and for greater comfort on board. Discover our offers to hire a catamaran, with or without a skipper.
- The traditional vessel and the schooner: characterful vessels, typically available as cabin cruises, a sociable way to explore the archipelago.
- The yacht: for a high-end cruise, with more space, comfort and amenities on board.
The services we offer for your Cyclades cruise
Depending on your sailing level and the atmosphere you are looking for, we offer several options for sailing in the Cyclades:
- The cruise with a skipper: an experienced skipper takes care of the navigation, guides you to the finest anchorages and knows every corner of the archipelago. An ideal option for enjoying the trip without taking the helm.
- The cruise without a skipper: for independent sailors who hold a licence, complete freedom to plan your own itinerary and stopovers at your own pace across the Aegean Sea.
- The cruise with a crew: in addition to the skipper, you can have a cook and even a hostess, for a stay with full comfort on board.
- The cabin cruise: you book a private cabin aboard a sailing boat or a catamaran, shared with other travellers on a set itinerary. A sociable and affordable option: discover our departures for a cabin cruise in Greece.
How much does a cruise in the Cyclades cost?
An 8-day / 7-night cruise in the Cyclades costs from €1,650 per person, across all options (with a skipper, without a skipper, with a crew or by cabin). The table below gives a rough idea according to the type of boat; the price then varies depending on the season and the model.
| Type of boat | Price per person (8 days / 7 nights) |
|---|---|
| Traditional vessel | €3,757 |
| Yacht | €3,093 |
| Sailing boat | €1,771 |
| Schooner | €1,650 |
Our insurance recommendations
- Cancellation insurance: it covers every member of the crew, whereas individual insurance or cover through your bank card will only cover the holder.
- Deposit waiver: at 5.5% of the charter price, this cover lets you recover a significant part of your deposit in the event of navigation-related damage (at anchor or alongside).
Request a personalised quote from our advisers.
Where to sail in the Cyclades?
The Cyclades archipelago brings together some of the most beautiful islands in Greece, separated by short distances: often 10 to 30 nautical miles between two stopovers (barely ten nautical miles between Paros and Naxos). Here are the must-sees:
- Santorini: the most famous island in the archipelago, of volcanic origin. Whitewashed houses, blue domes, coloured-sand beaches and spectacular sunsets over the caldera. Plan a stop with our boat hire in Santorini.
- Mykonos: the lively, cosmopolitan island, between bustling beaches, nightlife and seaside tavernas. See our boat hire in Mykonos.
- Paros: between tradition and modernity, with the lanes of Parikia, the fishing harbour of Naoussa and well-known kitesurfing and windsurfing areas. Discover our boat hire in Paros.
- Naxos: the largest island in the archipelago, between mountains, long beaches and ancient sites such as the Portara.
- Milos: the gem of secret beaches, with the white rocks of Sarakiniko and the sea caves of Kleftiko.
- Sifnos: the foodie stopover, renowned for its local cuisine and traditional villages.
A few nautical miles from Mykonos, the island of Delos, the mythological birthplace of Apollo, is a UNESCO World Heritage Site. To plan your route stage by stage, take inspiration from our sailing itineraries and our selection of the most beautiful islands in the Cyclades.
When to go on a cruise in the Cyclades?
The best time is May-June and September: calm seas, fewer crowds and temperatures of 20 to 24°C. The sailing season runs from May to October. In July and August the archipelago is at its hottest and busiest: it is also the peak of the meltemi, the northerly wind that typically blows Force 5 to 7 on the Beaufort scale, with gusts occasionally reaching Force 8-9 in exposed channels between the islands. A wind that delights experienced sailors but calls for confidence at the helm.
| Month | Air temperature | Sea temperature |
|---|---|---|
| May | 20°C | 19°C |
| June | 24°C | 22°C |
| July | 27°C | 24°C |
| August | 27°C | 25°C |
| September | 24°C | 24°C |
| October | 20°C | 22°C |
Indicative seasonal averages (air and sea).
Sailing conditions in the Cyclades
Sailing in the Cyclades is demanding but accessible: short distances between the islands, varied anchorages and favourable sailing conditions, provided you have a little experience or take a skipper on board. The main factor remains the meltemi: at the height of summer, it means choosing your stages carefully and favouring sheltered bays when the wind is strong.
Most boats anchor in coves or moor alongside the quays of fishing harbours. Some small harbours have limited depth and few berths in high season; catamarans, with their shallow draught, reach shallow coves more easily. It is worth planning your evening stopovers ahead, especially in July and August.
Do you need a licence to sail in the Cyclades?
Yes. For boat hire without a skipper in Greece, the regulations require on board a skipper holding a recognised licence or certificate of competence (for example the ICC, International Certificate of Competence, or the RYA equivalent), alongside a second experienced crew member. A restricted radio operator's certificate (VHF) is also required.
If you do not hold these documents, or if you would rather sail with peace of mind, opt for the cruise with a skipper: you enjoy the archipelago with no administrative requirements. For the full details of the documents required, see our FAQ on boating licences and regulations in Greece.
What to do during your Cyclades cruise?
Beyond the sailing, the Cyclades offer plenty of activities to share as a group:
- Water sports: snorkelling and diving around Milos and Paros, paddleboarding and kayaking to secluded coves, kitesurfing on Paros and Naxos thanks to the meltemi, or sea fishing for a dinner of fresh fish on board.
- Cultural activities: visiting the ancient sites of Delos, wandering the white lanes of Santorini and Sifnos, discovering the architecture typical of the Cyclades.
- Relaxation and nature: swimming at white-sand beaches such as Kolymbithres on Paros, peaceful anchorages and panoramic walks, in particular along the paths from Fira to Oia on Santorini.
Frequently asked questions about cruising in the Cyclades
How much does a cruise in the Cyclades cost?
A cruise in the Cyclades costs from €1,650 per person for 8 days / 7 nights, up to €3,757 on a traditional vessel. On top of the charter price, allow for extras such as the skipper's fee (for a skippered charter), fuel, the end-of-trip cleaning package and the security deposit.
What is the meltemi wind in the Cyclades?
The meltemi is a strong, dry northerly wind that blows across the Aegean Sea from June to September, typically reaching Force 5 to 7 on the Beaufort scale, with occasional gusts to Force 8-9 in the channels between the islands.
What is the difference between a skippered charter and a bareboat charter?
On a skippered charter, a professional skipper handles the navigation and manoeuvres, so no licence is needed. On a bareboat charter, you sail the boat yourself: this requires a recognised licence, an experienced crew member on board and a VHF certificate.
Where do cruises in the Cyclades depart from?
Most cruises set off from the harbours near Athens, such as Lavrio or Piraeus, located 30 to 45 minutes from Athens International Airport. Some itineraries also depart directly from islands in the archipelago.
When is the best time for a cruise in the Cyclades?
The best time is May-June and September: calm seas, temperatures of 20 to 24°C and fewer crowds. The sailing season runs from May to October.
Can you go to the Cyclades without knowing how to sail?
Yes. The cruise with a skipper or the cabin cruise let you discover the archipelago without a licence or sailing experience: a professional takes care of the helm and the manoeuvres.
How do you finalise the booking of your boat in the Cyclades?
As soon as we receive your request, an adviser will contact you by phone to understand your plans, then send you boat suggestions by email. Once the boat is chosen, you pay a deposit in your customer area to confirm the booking and secure the boat.
Ready to set sail? Start your search among our boats available in the Cyclades and get a personalised quote within a few hours.