Travel Greece

What to Expect from a Sailing Holiday in Greece

Greece is considered one of Europe’s most incredible places to explore for many reasons, and one of them is its beautiful islands. A sailing holiday is a dream way of cruising through the seas of the gods and fully experiencing the Greek islands. In the past, vacationing on a yacht has always been associated with power, wealth and luxury; today, the activity is now accessible to just about anyone.

Sailing gives you an opportunity to explore numerous Greek secret coves and beaches that are only accessible by boat. In addition, a chartered yacht service is the perfect floating base for other summer activities like windsurfing, fishing, and diving. Another great benefit of sailboat vacationing is that you avoid the crowds and hassle of long ferryboat rides.

If you are looking forward to turning your dream Aegean odyssey into reality, and explore top Greek islands, a sailing holiday is a way to go. However, you should keep in mind that things might not go as you intended during the sailing adventure. In this sense, here are a few pieces of advice on how to plan for a dream sailing holiday in Greece.

Where to Go and What to Do

To the east of the Greek mainland, you can easily access Athens as well as an itinerary of about 200 islands via the Cyclades archipelago. Some of the most popular destinations here are Naxos, Mykonos, and Santorini. You can also enjoy perfect tranquility by sailing to Syros, Sifnos and other lesser or smaller Cyclades.

It’s possible to sail about four hours between islands prior to anchoring at the main harbor or some secluded cove with an eight-day yacht charter in Ionian, for example. Sometimes, you can choose to anchor at a secluded spot, surrounded by nothing but water.

Furthermore, cycling and hiking on dry land or simply taking a swim off a boat, including scuba diving, are usually part of the itinerary. In addition, your skipper may make a few suggestions depending on the prevailing weather and wishes of your group. Keep in mind that the key to a successful sailing holiday in Greece is flexibility.

Combining several activities with sailing is a great way of breaking up the day with some awe-inspiring photography and painting. In fact, the best way to understand Greece is through cycling, snorkeling and scuba diving. Whatever you fancy can easily be arranged, but it’s a good idea to carry a book and have a glass of wine to top everything else off nicely.

What You Get

Companies renting out the boats offer you towels and sheets but washing and cleaning is your responsibility. While a skipper can help, this is not a fast rule or part of his job. Sailing holidays are more like camping out in an RV and especially great if you like getting close to nature and happy putting up with minor hardships.

However, you shouldn’t forget one critical point during your trip. The only fresh water you have is that which is in the tanks, so you need to be careful while using it – especially when showering. Fortunately, you can always replenish your fresh water supplies at any one of the numerous marinas and harbors.

How Much Will It Cost?

The costs vary depending on boat type, size and the season you are sailing. As it happens with hotels, the seasons are divided into low, medium and high peak depending on the demand. Peak season starts from end of July to the beginning of September.

However, you should keep in mind that if you’re chattering your own boat, the price per week will not include fuel and harbor fees. Fortunately, the latter is negligible since municipal Greek harbors charge about 3 Euros a day. In addition, charter boats have well-equipped kitchens that you should stock up and prepare your own meals on board to keep meals costs low.

Know Who is on Board

Greek sailing holidays usually take place in small groups, depending on the size of the boat. Most group sizes are eight to 17 passengers where, for instance, 12 passengers will live in two double cabins, twin cabins, and one triple berth cabin.

The boat’s skipper will usually allocate cabins once you arrive, and solo travelers get to share cabins with people of the same gender. In most cases, the boat skipper and crew are experienced sailors, with the skipper doubling up as a tour leader. On some tours, a host will accompany your group to ensure that everything runs smoothly.

Some tours, especially those run by marine conservation and wildlife watching programs, have an expert biologist or naturalist on board. When possible, the skipper and crewmembers are local for that personal touch in the history and culture of islands, as well as ensuring the local community benefits. For an intimate sailing experience, like for a honeymoon, you have the option of sharing with likeminded couples or hiring a private crew boat.

You don’t need to have sailing experience, but some trips may be more hands-on compared to others. It’s always a great idea to brush up on a few knots and sailing terms before you set sail. However, those with zero experience can learn sailing through experience.

Sailboat Living Conditions

While exploring Greece, you will come across a variety of sailing boats. For example, luxury gulets have four to eight en-suite cabins for accommodating up to 17 people. Note that luxury provides you with more space and modern conveniences to match the price tag.

Lesser opulent crafts feature an adventurous approach – much like camping, but out at sea! In such vessels, you will share bathrooms while electricity is minimal, and virtually no Wi-Fi to think of!

Most Greece sailing holidays take place on 44ft to 50ft monohull yachts that are designed to accommodate up to 11 passengers. The toilets are hand-pump operated and you should keep showers short so as not to test the patience of fellow passengers. In most cases, don’t look for hairdryers or plug sockets – make the most of the elements by staying up on deck and enjoy the beautiful Aegean sunsets.

Best Time for Sailing in Greece

July and August are the best months for sailing in Greece. The water and air temperatures are at their warmest, and nothing comes close to jumping off a yacht into the clear blue Aegean waters. However, if you have no sailing experience or prone to seasickness, these months are not the best times as they coincide with warm dry winds blowing from the north (Meltemi winds).

Meltemi winds are unpredictable and may occur even in clear weather, which makes it critical that you have an experienced local skipper with you. On the other hand, the winds make for an exhilarating sailing experience. To avoid the Meltemi winds and midsummer heat, it’s best to schedule sailing in May and September.


From May onwards, hundreds of yachts and boats sail the Aegean, offering visitors vacations marked with a close connection with nature and an unbeatable sense of freedom. Greece waters are particularly attractive playgrounds for experienced and novice sailors, dotted with numerous secret coves and beaches that are accessible via boat. In addition, a chartered yacht service offers you access to countless summer activities both at sea and on land.

About the author

Annie June Smithly