Whether you are Greek island hopping, sailing to specific Greek destinations for the purpose of a longer stay, or visiting on a Greek Island cruise the idea of sailing the Greek islands is one of the most sought after vacations in the world.  Exploring the Greek Islands and the mainland coast by sea allows you to access remote coves and bays and anchor in shallow water, close to the many stunning beaches. Sailing holidays in Greece can be hard to organise with a plethora of information online but not always the context and detail you need.

Which Greek islands to visit, how to book, what will it cost, what to pack for your sailing holiday. We answer these questions plus more in this Greece sailing guide.


The sailing season in Greece begins in May and lasts until the end of October. This is when the weather is best for sunbathing, swimming and making the most of the local hospitality.

Additionally, you will save some money and avoid crowds while visiting the islands in May, June and September particularly for the more popular ones like Santorini, Mykonos and Crete (which are very busy in summer).

Do you want to actually sail or are you happy to motor for your holiday? If you love to raise the spinnaker and ready about then you need to understand the wind and weather conditions in Greece. In particular there is a famous wind called the Meltemi which blows down from the Bospherous in Turkey in summer through the Cyclades and parts of the Northern Aegean Islands, and is particularly strong between June and September.

It is a bit unpredictable and doesn’t blow every day but when it does it can be so strong even the Ferries can’t run. In saying that sailors have loved the Cyclades for thousands of years for this very reason. It’s also why you see so many windmills on these islands. 

Strong winds can also be an issue in the Ionian islands. That said the beauty of these island groups is that you have lots of options. There are countless ports, coves and bays where you can shelter for a day or two and many beaches are often unaffected especially those facing south. As long as you display a degree of flexibility and understand your itinerary may often change you will always have a great time. 

Sail Greece – how to do it

Sailing around the Greek Islands has to be one of the great holidays in the world. It does, however, require a boat, preferably a yacht of some kind.

Even if you have no experience sailing it is still possible to explore the Greek Island by the sea with the following options;

Your Own Yacht

If you always tend to take sailing vacations, there’s a definite advantage in having your own yacht or boat and using it for your vacation to the Greek islands. If you live in Europe or the Middle East this could be a real possibility. Also, the great thing about it is you can feel in complete control and choose to explore the islands at your own time and pace without adhering to someones schedule.

A Party Cruise

A party cruise in the Greek islands is great if you just want to relax, have some fun and unwind, without having to worry about anything other than what to wear and who’s buying the next round of drinks. These tend to appeal to younger people and the young at heart and are often fairly inexpensive. They are a great way to meet people and a lot of fun done as a group.

Sail the incredible Saronic Islands with Contiki over 8 days from Athens.

Book a berth at Yacht Week Greece ( which actually goes for a few months)

Yacht charter Greece – a Bareboat Charter in Greece

If you are an experienced and competent sailor then you may prefer to skipper your own yacht and rent your own boat in Greece. Yacht Sailing Greece and Easysailing have big fleets, lots of variety and a range of options to cater to your needs. They can also organise crew and a range of addons.

Cost : depends on the type of vessel but generally it starts around US$1000 per day

Yacht charter Greece – a Skippered Yacht

Having a skippered yacht charter in Greece takes all the hard work out of it and allows someone else to sort out the route, the mooring arrangements, the navigation and even the weather. Your skipper will not only ensure you arrive to your destinations safe and happy but will likely also take you to hidden gems and pass on lots of local knowledge.

There are some great offers to consider such as sailing from Athens to Athens from Mykonos to Santorini or visit 9 of the Cyclades Islands with Intrepid.  You could also consider a skippered Gulet around the Dodacanese or 8 days cruising around the Saronic islands.

Cost: again varies greatly depending on the type of vessel and the inclusions. You will need to also budget for crew tips and will have to pay an APA ( Advanced Provisioning Allowance – usually around 30% of the total). It is ‘generally’ around 25% more expensive to rent a motor yacht than a catamaran.

Book a Greek Island Cruise

Finally, booking a cruise ship is great for simplicity, convenience and ease of access. You’ll be able to choose an itinerary that works for you and explore the Greek islands at your leisure, without having to own your own boat, understand maritime rules and restrictions nor skimp on luxury and comfort.

There are a number of big companies that operate regular cruises into and around Greece. It may not really be ‘sailing’ but for many people, it is the next best thing. There is a big variation in price point with these cruise with some very affordable itineraries on some ships and some luxury Greek Island cruises available as well.


Large cruises in the Greek Islands and Greece

Celestyal Cruises are the only operator that offer itineraries on a large ship focused ONLY on Greece

Princess Cruises have lots of Mediterranean itineraries that include Greece

MSC Cruises have huge ships that visit the most popular ports in Greece including Crete

Cruise Direct have access to over 20 cruise companies and cover all styles and budgets

Greek Island small ship cruises

Greek Island Hopper – this award winning small cruise  is pitched at the budget traveller and sails around the Cyclades islands over 11 days with no more than 50 passengers. 

MS Galileo is a grand 70 berth galeon that sails throughout the Cyclades starting and ending in Athens.

MS Running on Waves is a three-mast 42 berth yacht that sails through the Corinth Canal from Athens and explores the Ionian islands over 8 days

MV Harmony is a modern super yacht that explores the Cyclades islands, Samos and stops into Kusadasi in Turkey as well.

MS La Bell de L’Adriatique has 197 berths and sails from Dubrovnik to Athens through the Corinth Canal with a side trip to Meteora

Variety cruise from Athens taking in the Cyclades, down to Crete and up around the Peloponnese. We have done a cruise with Variety ( a Greek owned and operated company) and it remains one of the best holidays we’ve ever had!


Insider Tip


“The whole point of sailing for many people is the peace and tranquility so try and avoid using a noisy generator if you can, especially for airconditioning.

We found there was ample cool breezes at night in the Sporades if you left the windows open and used bug spray or coils”

Bella, Sydney Australia

Sailing holidays, Greece – what to pack

✔ Luggage – a small suitcase, preferably soft and waterproof and with very sturdy wheels

✔ Clothing 

Swimsuit x 2

Cover ups / sunshirts

hat or cap – preferably one that ties up and can not blow away

shorts – Maxi dresses are very tricky on boats!


long sleeve shirt(s)

a lightweight jacket

underwear for the length of the trip

activewear – versatile, easy to wash and will keep you cool

✔ Footwear

Fitflops/thongs are a given

Reef/surf shoes – you can buy these all over the islands but you will need them almost immediately. Mandatory for walking on the many pebbles and swimming to shore.

deck shoes or sneakers

optional going out shoe – something flat but perhaps with a bit of bling

✔ Small first aid kit



seasickness medication




✔ Toiletries

eco friendly shampoo/body wash or bar and lots of hair conditioner

lip balm


Insect repellent

makeup if you like but you won’t need much

a camera and or smartphone

✔ a waterproof pack for phone/camera

✔ chargers – phone, kindle, laptop etc…

preloaded music, videos and documentaries for quite nights in, lengthy stretches at sea or wet weather

✔ powerpack

a good book or two – the glare can make reading on a tablet or kindle difficult. Plus, water!

a waterbottle

A reusable shopping/beach bag

✔ a wetpack for dirty/wet clothes – packing cubes are usually great for this

towel pegs to peg your beach towel to a sunbed ( can also be used to hang shoes and clothes on the boat )

travel insurance

Further reading: What to pack for Greece, for women ( a complete packing guide)

Sailing holidays,Greece – where to go

Did you know that there are more than 6,000 islands and islets to be found among the Greek Islands? These cover most of the eastern Mediterranean, and among them 230 are inhabited. 

Whether you are sailing the Greek Islands for sun, sand and swimming, for the purpose of bird watching or checking out archaeological sites and relics it can be a great adventure regardless of how long you plan your sailing trip to be.

While there are many places worth visiting on the mainland, few places offer the kind of magic, tranquility and stunning natural scenery that you can find in the different island groups that make up the Greek Island archipelago. There are six different groups of Greek islands, plus Crete that you need to learn about, before planning your sailing journey:

The Cyclades islands

sail the cyclades


The Cyclades are probably the most popular of all the Greek Island groups. Here you can find islands like Paros, Mykonos, Andros, Naxos and Santorini with their picturesque villages and towns and distinctive whitewashed houses.

It is also where you will find Milos, home to the famous white volcanic beach of Sarakiniko and the towering white cliffs of Kleftiko.

The Small Cyclades group of islands is a firm favourite with sailors as well, offering a vast array of coves, bays and beaches and many are quite protected on windy days. The notorious Meltemi wind blows in July through to early September and can make sailing challenging and often exhilarating!

Most of the charter companies for this area base themselves in Athens or Paros.

Further reading : A complete guide to Schinoussa in the Small Cyclades


A Cyclades sailing itinerary

sailing greek islands

The Ionian Islands

sail the ionian islands

The Ionian islands are located in Western Greece close to Italy and have been variously occupied by the Venetians, French and British over time. There is substantial Venetian influence in the architecture and the culture including the food.

Islands include Corfu, Ithaca and Zante, and some of the smaller ones, like Paxi, which are great for a quieter pace. The island of Zante (Zakanythos) is home to much photographed Navaggio Beach, also known as Shipwreck Beach.

Due to less severe wind than in other regions these islands form the perfect ground for sailing holidays for everyone including less experienced sailors and families. Its proximity to the mainland also provides access to some famous ancient sites such as Olympia which can be visited from Katakolon.

The best bases for yacht charters can be found in Preveza, Corfu, Gouvia, Kefalonia and Lefkada.  

An Ionian Islands Sailing itinerary

sailing greek islands

The Saronic islands


The Saronic islands are found just south of the Greek capital of Athens, in the Saronic Gulf.

Salamina, Aegina, and Poros are among them, all famous for their beaches and for the influence that the contemporary Greek culture has on them. Hydra in particular if well known for both its vehicle and scooter ban as well as being home to many literary greats and the original ‘bohemians’.

This is one of the easiest island groups to sail in Greece as they are close to Athens and are generally protected from strong winds meaning the seas are often quite calm. This also makes it the most popular area to sail in Greece.


A Saronic Islands Sailing itinerary

sailing greek islands

The Dodacannese islands


This group of Greeks Islands hugs the Turkish mainland and is also one of the largest. There are 163 islands to explore of which 26 are inhabited.

Due to its proximity to Turkey, the Dodecanese islands have a strong Ottoman influence in the architecture and culture. At various times they have been fully occupied by the Venetians and the Ottomans and in turn parts of modern-day Turkey were once Greek.

Highlights in the Dodacanese include the Palace of the Grand Master of the Knights of Rhodes, the beautiful harbour in Symi and colourful Kastelorizo. 

The top yacht charter companies have their bases in Rhodes and especially in Kos. Other charter bases in the area are Bodrum, Marmaris and Fethiye in Turkey.  


A Dodacanese islands sailing itinerary

sailing greek islands

Northern Aegean islands


Although located slightly farther away from the regular tourist trail and often associated with Turkey due to their proximity to the Turkish mainland, the North Aegean islands are still excellent spots for a holiday.

With islands like Lesvos and Samos being counted among the top holiday destinations of the area, there’s still a lot to explore here, especially since some of the islands feature pristine beaches that have yet to be touched by tourism.

Chios is also a fascinating destination with it’s ‘painted’ village of Chios as it’s fragrant Mastica bushes.


North Aegean Sailing itinerary

sailing greek islands

The Sporades islands

sailing greek islands

The Sporades group of islands is quite close to the mainland port (and airport) of Volos, which makes them easily accessible if you decide to sail from that direction.

There are 11 islands in total with 4 permanently inhabited. Several of the beaches on Skiathos and Skopelos are considered the best in the eastern Mediterranean and by sailing there are an abundance of stunning bays to drop anchor where you will be all by yourself. In fact the Northern Sporades are as famous for their beautiful scenery and beaches as well as the amount of secluded anchorages and wildlife.

With over 60 stunning beaches, several sailing companies organise daily ferry rides and even a marine park established around the islets just north of Alonissos. 

For this sailing area the best base is the marina in Skiathos port.  


A Sporades Islands Sailing itinerary 

sailing greek islands


sailing greek islands

Crete is like a country all on its own with hundreds of kilometres of coastline to explore. You will find pink beaches, crystal clear water, turtle nesting, mythical ruins, ancient caves and much more.

The weather in Crete is also the mildest and offers more sunny days and less strong wind that the others.

For visitors that bring their own yacht or for those that have a lengthy skippered charter the normal approach is from the South Peloponnese, via the island of Kythira, to Kourtri or Paleohora for the southern coast or Kissamos and Chania for the northern coast.

When leaving the island from the East many people depart from Cape Sideros and sail via Kasos and Karpathos on to Rhodes and the Dodacannese islands.

A Crete Sailing itinerary

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