Table of Contents

Is Sailing in Greece your next travel goal? Read the ultimate guide to organize your sailing holidays in Greece & get all the insights from Santorini Experts.

Sailing in Greece is by far the ultimate way to explore the islands or the coast of the Greek mainland and get the best out of your summer holidays in the country.

If you have a wanderlust for the Mediterranean beauties and know your way around a boat (or are willing to hire a skipper), then you can start planning your sailing holidays in Greece right here. Get up to speed with a guide created by Santorini Experts and make all the right choices before living it up.

Is Greece good for sailing?

Greece is renowned as a premier sailing destination, offering idyllic island-hopping opportunities, crystal-clear waters and favorable wind conditions.

Its warm, sunny climate and strategic position at the end of the sheltered Mediterranean make it an excellent choice for sailing enthusiasts of all levels!

Sailing holidays in Greece are the best way to explore the country

The Greeks have been soaring the Mediterranean since the Minoan era and Greek mythology and history have been heavily influenced and shaped by the sea culture. The most famous sailing trips in ancient Greece are those of Jason, with the expedition of Argo, and Odysseus, who sailed for 10 whole years trying to get home to Ithaka.

The Ultimate Guide to Organize your Sailing Holidays in GreeceFree Photos by Pixabay

The Aegean Sea is full of majestic islands and islets with popular harbors and petite unexplored coves brimming with legendary stories of ancient times next to sounds of the everyday hassle of modern life.

A sailing boat in Greece can take you to places where other transportation means, like cars, can’t. From well-known fun hubs to secluded beaches, you can genuinely uncover almost any place worth visiting, following the heroic trails of ancient seafarers.

What is the best season for sailing in Greece?

Undoubtedly the best season to visit Greece would be from spring to fall. And that’s approximately where the sailing season lies. You can find sailing boats to rent in Greece from April all the way to October. However, keep in mind that the high sailing season is from mid-July to mid-September, an essential factor to take into consideration regarding prices and availability.

During that time, all stores, restaurants, and archaeological sites are open. Furthermore, most islands and coastal towns have their share of crowds of holidaymakers and are jam-packed with activities and party spots. Last but not least, for most people, the water temperature is suitable for swimming and diving from May to September, making those months ideal if you’re dreaming of dipping at any given chance.

The Ultimate Guide to Organize your Sailing Holidays in Greece

What you need to know about the winds in Greece

The Aegean Sea is dominated by the “Meltemi” winds from the north, especially during July and August. In the Beaufort wind scale, they can reach up to 7-8 Beaufort and can last for a few days, so it is particularly important to plan your sailing holidays in Greece. The Meltemi blows all day up until the evening, usually being strongest in the early afternoon.

Dealing with the Meltemi winds if you’re visiting a single Ionian island is one thing, but when it comes to sailing around the Greek islands of the Aegean, there are a few more things to look out for. Check the weather conditions frequently and take every necessary precaution. And of course, never leave the dock without an extra jacket!

The Ultimate Guide to Organize your Sailing Holidays in GreecePeggy and Marco Lachmann-Anke by Pixabay

What to pack for your Greek sailing trip

  • Swimming suits
  • Sunglasses
  • Sunhat
  • Sunscreen
  • Clothing, including T-shirts, short pants and light jackets
  • Travel toiletries
  • Micro-fiber beach towel
  • Water shoes
  • Portable charger
  • Plug adaptor
  • Table games

Sample itineraries for sailing trips in Greece

There is a wide range of trips and itineraries for dreamy sailing vacations in Greece, yet since weather conditions can be quite fluid, always consider mixing and matching according to the forecast and your personal needs and wants.

Plus, a smooth sailing experience is the goal, so the distance between two destinations is always calculated and planned accordingly. Liaise with your charter company to craft the best possible itinerary that speaks to you.

The Ultimate Guide to Organize your Sailing Holidays in GreeceNorbert Graupe by Pixabay

Here are four suggested itineraries for sailing trips in Greece, which are all-time favorites. You can choose to stay at each destination for as many hours you like, perhaps even days. And this exactly is where the beauty of chartering a boat lies – it is you who gets to decide!

➔   Southern Cyclades Sailing Itinerary- Start/Finish Santorini

The Ultimate Guide to Organize your Sailing Holidays in Greece

Discover Folegandros, Sikinos, Ios & Astypalaia

  • Folegandros: Start your sailing journey in Greece on the rocky island of Folegandros, which is covered by rugged hills with white houses. Despite having been a place of exile for centuries, you’ll find nothing downbeat about the island now, with its many beaches and hiking routes.

Favorite beaches: Agkali, Karavostasis, Ano Meria & Agios Georgios

  • Sikinos: A destination of rustic beauty, Sikinos, is the perfect stop before the cosmopolitan Ios. Its peaceful character will let you take a closer look at the traditional life on Greek islands and swim in remote coves. If you’re lucky, you’ll stumble upon one of the festivals held during the summer and get to taste local products like cheese or honey.

Favorite beaches: Agios Georgios, Dialiskari, Alopronoia & Malta

Santorini First Impressions Private Tour

  • Ios: No Cyclades sailing trip in the Greek islands would be complete without spending some time in Ios. There’s a perfect element for every taste, from the picturesque scenery of windmills and blue-domed churches to the sandy beaches and lively nightlife. Party away or explore the island villages for a quieter experience and a stunning sunset view from Palaiokastro.

Favorite beaches: Magganari, Agia Theodoti, Mylopotas & Kalamos 

  • Astypalaia: Let the lovely Chora scenery sweep you off your feet as you approach Astypalaia. This is an ideal stopover for toned down moments in small bars with a balcony and tavernas with freshly-caught fish cooked just the way locals love it – and you will too! Don’t miss the chance to walk up to the charming 14th-century castle and admire the sea view from atop.

Favorite beaches: Kaminakia, Livadi, Kounoupi & Koutsomiti

➔   Northern Cyclades Sailing Itinerary – Start/Finish Lavrio

The Ultimate Guide to Organize your Sailing Holidays in Greece

Discover Kea, Syros, Serifos & Kythnos

  • Kea: This delightful island, one of the closest to Athens, holds some of the most appealing natural sceneries with oak forests and rich vegetation. Many parts of Kea, protected by Natura 2000, fascinate visitors who take the time to look further inland beyond the barren coastline.

Favorite beaches: Koundouros, Otzias, Korissia & Pisses

  • Syros: Unlike most neighboring islands, Syros has neoclassical buildings all around its capital, Ermoupoli, a large square with a grand theatre and a remarkable history. It is one of the very few places on earth where Greek Orthodox and Catholic churches collaborate to celebrate Easter together in harmony. On Syros, you’ll find exquisite cuisines and finger-licking sweet delights.

Favorite beaches: Galissas, Kini, Megas Gialos, Azolimnos & Vari

Santorini Caldera Sailing Cruise on a Luxury Yacht

  • Serifos: Behold the island of the Cyclops who made the life of Odysseus a bit more difficult before returning home. However, Serifos is not only famous for what is thought to be the Cyclop’s throne. A mesmerizing seabed is loved among diving fans and you’ll never get tired of relaxing at a cafe at the quaint Chora (Town).

Favorite beaches: Livadi, Ganema, Sikamia & Megalo Livadi

  • Kythnos: Life is easy in Kythnos. This is where you can get lost in one of the numerous beaches and walk almost everywhere. The village Loutra (meaning baths) deserves a visit, especially if you’re in for a swim at the area’s thermal baths, and the archaeological site nearby with a 10000-year-old settlement is an essential attraction on this low-budget island.

Favorite beaches: Kalo Livadi, Loutra, Merihas & Kanala

➔   Sporades Sailing Itinerary- Start/Finish Volos

The Ultimate Guide to Organize your Sailing Holidays in Greece

Discover Skiathos, Alonnisos, Kyra Panayia or Peristera, Skopelos & Trikeri

  • Skiathos: Pretty and modern, the first stop of the Sporades itinerary awaits introducing you to its Medieval castle hanging on a rocky hill and its cosmopolitan port. It could be the all-around links to history, the (divided in two) island of Bourtzi, or the white houses among olive groves, but most people agree that Skiathos is what dreams are made of.

Favorite beaches: Koukounaries, Troulos, Kolios & Lalaria

  • Alonnisos: Inhabited during the Neolithic era, Alonnisos has played a crucial role through the years, from antiquity to modern days – Jason with the Argo also made a stop here. Half of the island is proud of its rugged handsomeness. In contrast, the other half consists of turquoise waters, home to rare Mediterranean species and is protected by the Natural Marine Park of Alonissos.

Favorite beaches: Patitiri, Votsi, Steni Vala &  Agios Dimitrios


  • Kyra Panayia or Peristera: The whole point of renting a sailing boat in Greece is – amongst other reasons – the opportunity to sail around each island and explore smaller uninhabited islets that are sometimes unheard of even to locals. Such are Kyra Panagia, home to monks, and Peristera with a 19th-century lighthouse.
  • Skopelos: The amphitheatrical Chora and the castle from the top captivate visitors in Skopelos, first inhabited by the son of the Olympian god Dionysos, Peparethus. The rich vegetation of olive groves and pine trees makes Skopelos stand out and popular among locals and foreigners – the 2008 motion picture Mamma Mia was filmed here.

Favorite beaches: Stafylos, Agnontas, Neo Klima & Kastani

  • Trikeri: Home to very few residents, Trikeri is a lovely little island to explore from coast to coast or walk around – it will only take you three hours to reach its other side. You can enjoy a cup of coffee or a traditional meal with a stunning view.

Favorite beaches: Afetka, Agia Sofia & Prasini Ammos

➔   Saronic Gulf & Eastern Peloponnese Sailing Itinerary – Start/Finish Athens

The Ultimate Guide to Organize your Sailing Holidays in GreeceLisa Larsen by Pixabay

Discover Poros, Dokos, Spetses, Nafplio, Porto Cheli, Hydra & Agistri

  • Poros: Welcome to the romantic Saronic island of Poros. Whether you feel like walking around the town, built on a hillside, or watching the sunset next to the imposing Clock Tower, your sailing trip in Greece should start here. Souvenir shops, restaurants and cafeterias will give you just the right amount of energy to keep you going.

Favorite beaches: Megalo Neorio, Monastiri, Love Bay & Panagitsa

  • Dokos: A well-kept secret among skippers, the isle of Dokos is known for its clean beaches and alternative tourism. Visit the lighthouse, built-in 1923, and relax in an almost uninhabited piece of land next to wild scenery.

Favorite beaches: Kouverta & Bisti

  • Spetses: Counting 5000 years of life, Spetses is an island, both historical and modern. Walk along the beautiful roads with old yet charming houses, the neoclassical architecture, and the colorful Old Harbour.

Favourite beaches: Agia Marina, Ligoneri & Kouzounos

  • Nafplio: We dare you not to fall in love with the first capital of Greece. Nafplio is a city where emblematic buildings, like the old Parliament and neoclassical beauties with blooming balconies, paint a wicked picture everywhere you look. Stroll around, bathe or dine in a scenery of pure romance.

Favorite beaches: Arvanitias, Karathonas & Neraki

  • Porto Cheli: This eastern Peloponnese jewel of a town with fantastic beaches and delightful coastal scenery attracts Athenians and many travelers alike. A cosmopolitan marina and sea-view eateries will keep you occupied for many hours in Porto Cheli.

Favorite Beaches: Nikki beach, Costa, Hinitsa & Korakia

  • Hydra: Next, sail away to the car-free island of Hydra where people move around on foot, by bike, or on their donkey. A relaxing must-see island in the Saronic with many hidden treasures like clear-water bays with sandy shores.

Favorite beaches: Vlichos, Mandraki & Klimaki

  • Agistri: The historic churches on the island and the windmill in the village Megalochori remind us of the island’s traditional life. Other than that, the tranquil ambiance allows travelers to unwind at the sea-wrapped Agistri.

Favorite beaches: Megalochori, Skala & Limenaria

Sailing in Greece on a Sailing Catamaran or a Sailing Yacht?

One of the most important decisions to make before setting out on a sailing trip in Greece is the type of boat that accommodates your needs. The two types of sailing boats that are most common to rent in Greece are sailing catamarans and sailing yachts.

The Ultimate Guide to Organize your Sailing Holidays in Greece

Yachts (or monohulls) use their sails or an engine to move, or sometimes even both. Due to its size, it is easier to find a berth at the marina or a port for a yacht – it is significantly narrower than the catamaran. Speed is not a yacht’s strong suit; however, the ride tends to flow more smoothly and comfortably.

Sailing catamarans (or multihulls) have two engines that can be used as well as sails. This can make navigation a whole lot easier since they are better at maneuvering. Usually, they are relatively wider and that’s why larger groups of people, like families, tend to go with this choice for their sailing trips in Greece. Larger areas can entertain more guests.

What you need to know about sailing boats before your charter

All in all, the choice comes down to personal preferences. Factors like safety and stability are – give or take – the same, according to most people. The speed depends solely on the boat’s length; thus, the larger the boat, the faster you can sail. However, bear in mind that anchorage is slightly more difficult for sailing catamarans and, generally speaking, more experienced sailors usually go with this choice.

The Ultimate Guide to Organize your Sailing Holidays in Greeceavpteam by Pixabay

Yachts have the additional advantage of being environmentally friendly since the motive force is the wind. The truth is that sailing without the sound of an engine can make for a lighthearted cruise and elevate your experience. If you are looking for a genuine sailing in Greece endeavor with an endless sensation of a wind-beaten journey, then a sailing yacht is definitely suggested.

What is the difference between a bareboat charter and a crewed charter?

Choosing between a bareboat or a crewed charter is key before your sailing holidays in Greece. If you are a licensed sailor (ideally with experience), then a bareboat charter allows you to be more spontaneous during your holidays. At least two persons from the group must have a recognized skipper’s license but make sure you know your whereabouts if you plan on sailing without a skipper, especially if you’re visiting a region for the first time.

On the other hand, a crewed charter can include a skipper or both a skipper and a hostess. This isn’t only for inexperienced travelers, but for those of you who are after a more laid-back sailing vacation in Greece. Putting your feet up and letting someone else steer the boat and take care of you is a whole other kind of voyage.

Apart from steering, your skipper is also there to help translate things at your destinations and act as a tour guide – they always know where the tasty food and the good coffee are served. Sit back, relax and enjoy your holidays in Greece with a skipper.

The Ultimate Guide to Organize your Sailing Holidays in GreeceFrancine Screca by Pixabay

FAQs for sailing in Greece

Is sailing in Greece difficult?

Even though the difficulty level varies depending on the region and weather conditions, sailing the Greek islands is relatively easy and, most importantly, safe if you follow the guidelines. Be sure to check the weather prediction and stay up-to-date with the announcements of the local authorities.

What do you wear on a sailing holiday in Greece?

Sailing in Greece is a breeze, as shorts and a T-shirt are all you’ll need, apart from your swimsuit, of course. Sunglasses are a basic necessity and some people find windproof jackets essential, depending on the season. You can include an outfit for dining but always keep it casual.

How much does it cost to charter a sailboat in Greece?

Just like hotels, sailboat prices vary depending on the season – the high season would be significantly more expensive than the low season. And of course, a bareboat is undoubtedly cheaper than a crewed charter. In addition to that, boats come in many shapes and sizes and can include various services, and factors like the number of cabins they have and the year they were built in also play a role. High season prices can range accordingly:

Bareboat sailing yacht: 2500 – 7000 euro per week

Crewed sailing yacht: 6000 – 10000 euro per week

Bareboat sailing catamaran: 4500 – 10000 euro per week

Crewed sailing catamaran: 12000 – 60000 per week

What is the best way to island-hop in Greece?

Hopping from one Greek island to another by ferry or by sailing boat is by far a favorite choice. Boats give you the flexibility of visiting your preferred destinations without sticking to a strict schedule and can reach shores that are sometimes only accessible by sea, or much faster and easier to do so.

Do you need a license to sail in Greece?

It depends on the type of boat you’ll choose. If you opt for a bareboat charter, at least 2 persons from your group must possess a recognized skipper’s license. On the other hand, if you rent a crewed charter, you don’t one as your skipper will undertake the steering.

Table of Contents
Share This Story

Related Articles

Information, news and secret tips about Santorini