Greece from the sea: 14 days on a yacht in the Cyclades

There are trips in Greece where you hop from island to island by ferry, pack your bags every two days and look for another hotel. And there's a completely different way: take the hotel with you. For two weeks, the yacht is your bedroom, your terrace over the sea, your transport, and the only way to reach coves no road leads to.

This guide is a working plan for a group of 12 (an extended family or a group of friends) that wants to do it right: exactly what to rent, what it really costs, how to manage without a sailing license, and what a 14-day route through the Cyclades looks like, day by day.

Why two weeks, and why a catamaran

Four days in the Saronic Gulf are an excellent taste of sailing; we wrote about them separately in four days in the Greek islands by yacht. Two weeks are another story: enough to leave the sheltered gulfs and sail a real loop through the Cyclades, see both the famous islands and the quiet ones, and still leave spare days for the weather.

For a group of 12, a sailing catamaran is almost always better than a monohull yacht. It's much wider, rolls less (which matters a lot to anyone prone to seasickness), and has a large saloon, open spaces at the bow and stern, and several bathrooms instead of one. In practice, on a group charter, the difference between a catamaran and a regular boat is the difference between a shared holiday and constant crowding.

What exactly to rent for 12 people

The most comfortable choice is a 40 to 46-foot sailing catamaran with 5 to 6 cabins. As of 2026, companies like Istion offer catamarans for 12 guests at their Lavrion base: models such as the Lagoon 400 S2 and newer catamarans from the Excess range. Prices vary a lot by month, the boat's age, availability and promotions.

An easy point to miss: if you're 12 travelers and also hiring a skipper, don't settle for the listing saying "12 berths." Ask explicitly where the skipper sleeps, and whether there's a separate crew cabin. Otherwise one of you will discover on boarding day that they're sleeping in the saloon.

No sailing license? Not a problem

All the big charter companies in Greece let you book a skippered charter: the boat is entirely private to your group, but a professional skipper lives aboard and runs the sailing: navigation, entering and leaving harbors, mooring, safety, and adjusting the route to the forecast.

As of 2026, a typical price for a skipper is €180 to €220 a day. Ionian Charter's price list, for example, shows €200 a day plus the skipper's food, which comes to around €2,800 for two weeks.

Want a more pampered holiday? You can also add a hostess or a cook. The same price list shows about €180 a day for a hostess and €190 a day for a cook, plus the crew's food.

And if you do have a license

On a bareboat charter, at least one person in the crew must hold a valid sailing license recognized by the company and the Greek authorities, and usually a second competent crew member is required too. Don't assume a particular Israeli license will be accepted automatically: send a copy to the charter company before you pay, and ask for written confirmation.

Why set out from Lavrion

Lavrion is southeast of Athens, about an hour's drive from the airport, and makes a very convenient departure point toward Kea and the rest of the Cyclades. The first leg from Lavrion to Kea is only 12 to 18 nautical miles: a short, pleasant opening day instead of starting with an open-sea crossing.

Days 1 to 4: from Lavrion to Kea, Kythnos and Syros

Day 1: Lavrion, boarding your new home

The first day is for getting organized: taking over the boat, going through the safety equipment, photographing existing scratches before you leave, and stocking up on food, water, coffee, ice and fruit.

Do the big shop here, on the mainland. On the small islands the selection is narrower and prices are higher.

Day 2: Lavrion to Kea

Distance: about 12 to 18 nautical miles. Anchor at Vourkari, swim in the afternoon, and in the evening go ashore to a taverna at the water's edge. If you want a little dry land, you can go up to Ioulida, the island's capital, and wander its alleys.

Day 3: Kea to Kythnos

Distance: about 20 nautical miles. One of the most beautiful stops on the route is Kolona beach, a narrow strip of sand joining the island to a small islet and forming two bays, one on each side. In the Loutra area you can also find hot thermal springs that flow into the sea.

Day 4: Kythnos to Syros

Distance: about 22 nautical miles. Ermoupoli is a surprise: an elegant capital with neoclassical buildings, a marble-paved square, cafes and restaurants, much less "tourist island" and much more a real Greek town. Toward sunset, it's worth going up to Ano Syros above it.

Days 5 to 8: Mykonos, Delos, Paros, Ios and Santorini

Day 5: Syros to Mykonos, with a stop at Delos

Distance: about 20 to 26 nautical miles. In the morning, stop at Delos, one of the most important archaeological sites in Greece and a UNESCO World Heritage Site: a whole island that is essentially an ancient city. In the afternoon, continue to Mykonos: Little Venice, the windmills, and nightlife for anyone who wants it.

Day 6: Mykonos to Paros

Distance: about 26 nautical miles. Naoussa is an excellent place to moor: an old fishing harbor turned into a street of restaurants, with dinner right on the water. If the sea is calm, it's also a good day for a swim stop on the way.

Day 7: Paros to Ios

Distance: about 25 nautical miles. Ios is known mostly for its nightlife, but it works very well for families too: choose a quiet bay, spend the day there, and only go up to the Chora in the evening. It's one of the prettiest in the Cyclades.

Day 8: Ios to Santorini

Distance: about 20 nautical miles. Arriving in Santorini by sea is half the experience: the caldera walls rise hundreds of meters out of the water, and the white villages sit on top of them like snow. From there you can go up to Oia or Fira, or cruise out to the volcanic islands in the middle of the caldera.

Note: mooring in Santorini is relatively tricky (deep water, few sheltered spots), and the skipper is the one who decides where and how. It's also a night when many groups choose a paid berth over a free anchorage.

Days 9 to 14: Folegandros, Milos, Sifnos and back

Day 9: Santorini to Folegandros

Distance: about 30 nautical miles. Folegandros is far calmer than Santorini, and that's exactly the point. The Chora sits on top of a cliff and suits an evening of a small taverna, Greek wine and wandering with no schedule.

Day 10: Folegandros to Milos, and Kleftiko

This day is one of the high points of the whole trip. Kleftiko is an area of white cliffs, natural arches and sea caves you can reach only from the water; historically it was a pirates' hideout. Just drop anchor, grab a mask and snorkel, and get into the sea.

Day 11: Milos to Sifnos

If the timing allows, add Sarakiniko on Milos in the morning: a white rock landscape that looks like a moon landing. From there, sail to Sifnos, an island famous in Greece above all for its food. This is the evening to book a good restaurant in advance.

Day 12: Sifnos to Serifos

Serifos is less touristy than its famous neighbors. Go up to the Chora toward sunset and look down on the harbor, your boat and the sea from above.

Day 13: Serifos to Kythnos

Start heading back toward the mainland. This day is also the route's safety cushion: if the weather held you up on an earlier day, this is where you catch up without pressure.

Day 14: Kythnos to Lavrion

Distance: about 27 nautical miles. Get back to the base on time, refuel, clear out your gear and go through the boat inspection before you disembark. If your flight is the same day, leave a big margin, because the return inspection takes time.

What it really costs

Estimates for two weeks, for the whole group, as of August 2026:

• Catamaran for 12 people: €15,000 to €23,000, depending on season, model, the boat's age and promotions.
• Skipper: about €2,800 (at about €200 a day), plus food.
• Hostess (optional): about €2,520 (at about €180 a day).
• Cook (optional): about €2,660 (at about €190 a day).
• Fuel, water and harbor fees: from several hundred euros up, depending on engine hours and how many nights you spend in a marina rather than at anchor.
• Cleaning and mandatory extras: varies; check the transit log, bed linen, the dinghy, the outboard motor and so on.

The number to remember: for a group of 12, a reasonable starting point for planning is €22,000 to €30,000 for the whole group for two weeks with a catamaran and skipper, before flights. Divided by 12, that's on the order of €1,800 to €2,500 per person, with lodging and transport between the islands and coves included.

Where to look for a yacht

• Istion Yachting: a large Greek charter company, with bases in Athens and Lavrion.
• Click&Boat: a large boat rental marketplace, including catamarans with or without a skipper.
• SamBoat: another comparison site, with filters for number of passengers, boat type and skipper.

In every case, get a written quote before you pay a deposit, and check it for cancellation terms, insurance, the security deposit amount and the list of mandatory costs.

Seven questions to ask before you book

1. Are the 12 places 12 guests in addition to the skipper?
2. Where does the skipper sleep? Look for a separate crew cabin.
3. Which mandatory extras aren't included in the price? Final cleaning, the transit log, bed linen and towels.
4. How big is the security deposit, and can you insure it? Deposit insurance is much cheaper than leaving the full deposit.
5. Is there a dinghy with an outboard motor? Without one, you swim ashore.
6. Is there a watermaker? For a group of 12, it makes a big difference to your freedom of movement.
7. How many fridges and freezers are there? For 12 people over two weeks, one small fridge isn't enough.

When to sail

July and August are peak season, but also when the meltemi winds in the Cyclades can blow hard and disrupt sailing days. For a two-week route, June and September are usually the best choice: still warm, pleasant water, less crowding in the harbors and lower prices.

The route is a plan, not a contract with the sea. If the skipper changes destination because of the wind, listen to the skipper.

Small tips that make a big difference

• No hard suitcases. A soft bag you can fold and push under the bed. There's no room for suitcases on a boat.
• Fewer clothes than you think. You'll be in a swimsuit most of the time.
• Shoes: on deck, go barefoot or wear only clean deck shoes with light soles.
• Seasickness: if you're prone to it, talk to a doctor or pharmacist in advance instead of waiting for it to happen.
• Power banks: electricity on the boat is limited at anchor, especially with 12 phones.
• Internet: ask the company for a data package or get an eSIM. Reception is good on most islands and fades between them.
• SUP: a paddleboard completely changes your stops in the coves, and you can usually add one to the rental.

And what about kids on a boat

A catamaran can be excellent for a family holiday, but you have to treat it as a marine environment, not a hotel room. With small kids, you can ask in advance for a safety net around the deck, make sure there are life jackets in the right sizes, and set clear rules for sailing time ahead of time. If you're unsure about ages and pace, you'll also find value in the guide to Greece with kids.

The bottom line

A trip like this takes more planning than a regular hotel holiday, but in return you get something that's hard to recreate any other way: waking up in an empty cove, jumping into the water before coffee, sailing to another island, anchoring beneath the cliffs of Milos, and ending the day at a small taverna on Sifnos.

14 days. 12 people. Dozens of coves and islands, and one hotel room that never stops moving.

And the part before and after the sailing

The sailing is only part of the holiday. Before and after it there are flights, days in Athens and the logistics of a large group. Diretix builds the frame around the sailing for you: days in Athens, attractions, lodging and an estimated budget, matched to your group's pace and makeup, in minutes. One trip a month is built in full, for free, up to 12 days.

Photo credits and sources

The photos in this article are from Wikimedia Commons under open licenses:

• Yachts at Kleftiko, Milos: dronepicr, CC BY 2.0.
• Cliffs and caves at Kleftiko: dronepicr, CC BY 2.0.
• The windmills of Mykonos: dronepicr, CC BY 2.0.
• The ruins of Delos: Romain Delanoe, CC BY 2.0.
• Oia, Santorini: Misty, CC BY 2.0.

Sources for prices and the route: Istion: special offers, Istion: bareboat requirements, Ionian Charter: price list, Easy Sailing: a two-week Cyclades itinerary, Drivas Yachts: 14 days in the Cyclades.

The prices in this article are estimates checked in August 2026 and are for budget planning only. Charter prices change with dates, availability, model, promotions and exchange rates, so before you book, get a written quote from the charter company and confirm the cancellation terms, insurance, deposit, licensing and mandatory costs.