Sailing & Cruising in Greece [vacation packages, itineraries & yacht rental tips]

So, you’re planning on going on a sailing trip to Greece? But, you don’t know where to start from?


No, worries, we got you covered!


In this article, we’re going to let you in on every secret about sailing in Greece, including the best places for sailing, insider tips, and many more. Keep reading!

Sailing Cruising Yachting Greece


What are the sailing vacation categories?


Bareboat charter

Are you or a fellow traveler a certified skipper? If the answer is yes, you can opt for a bareboat charter, which means that you aren’t going to hire a skipper to guide your boat. This option is perfect for those who are experienced sailors and adventure seekers, know how to navigate through the Greek islands, and want utmost privacy and freedom.

However, bareboat charter comes with some drawbacks. First of all, at least one of the boat’s passengers must own an RYA Day Skipper International Certificate of Competence or equivalent certification to run the boat. Second, the licensed skipper must be familiar with the route you’re going to follow and the wind conditions in the different parts of the sea in Greece. Navigating through the several island complexes will definitely be challenging for someone who hasn’t done it before!

Skippered charter

A skippered charter is a great option for those who aren’t certified skippers or just want to sit back and enjoy the trip. Hiring a skipper you’ll have a professional to guide the boat and save you from the stress of navigating through unknown waters, making sure you’ll arrive at your destination safely. What’s more, a local skipper knows better than anyone the most beautiful caves, beaches, and coves. This means that not only you’re going to discover the hidden gems, but you’ll also save time!

How much you’re going to spend on a skipper depends on the season and the vessel type you’re going to choose for your trip. An indicative price for hiring a skipper in the summer season is about 1,000 euros per week. For three persons, this means less than 50 euros per person/day, which is less than the price you’re going to pay for a hotel.

Crewed charter

If you want to have a luxurious sailing experience in Greece, a crewed charter is your best bet! With a crewed charter, you’re going to have -except for the skipper- chefs, hostesses, etc, who will go out of their way to meet your every need during the trip. The only thing you’re going to do is sit back and enjoy the trip, without worrying about cleaning, cooking, and other mundane tasks that you should avoid during your holidays. If you worry about being on a boat with a crew of strangers, well, don’t! The crew and the skipper are trained to be discreet and respect your privacy.

Where to sail in Greece


With about 6,000 islands and islets, most of them uninhabited, it may be hard to choose where to go! If you opt for a bareboat charter, we suggest sticking with the tried-and-tested routes. But, if you choose a skippered charter, you can go off the beaten tourist trail and discover many hidden islets. Below you’ll find the most popular sailing destinations in Greece.


Sailing around the Cyclades islands


The Cyclades is the most popular island group in Greece. Hordes of tourists flock to the Cyclades every year to visit its super-star islands, Mykonos and Santorini, do watersports in Paros, and party in Ios. Those who seek privacy and want low-key holidays away from the hustle and bustle go to the so-called Small Cyclades, an island complex that includes Naxos, Koufonisia, Schinoussa, and Donoussa.


Although most of the people that go to Greece for sailing holidays want to go to the Cyclades, this island group is a tricky option for sailing for two main reasons. Firstly, it’s quite far from Athens, meaning you’ll need at least 8 hours sailing per day to get there. Secondly, the Cyclades islands are often affected by the northern Meltemi winds that blow in the Aegean from late July to August, causing big waves. The wind conditions make sailing challenging, as the wind can reach the 8 Beaufort.


However, if you want to go to the Cyclades, we suggest setting off on your sailing trip from a Cycladic island and not from Athens. You can reach the island of your choice by air or by boat from Athens and then charter a yacht there, instead of sailing from Athens. This way, you’ll save yourself from endless hours of sailing and have a more pleasant trip. Our second advice is to opt for early summer or fall when the Meltemi winds aren’t strong. However, even if you visit the Cyclades in the Meltemi season, an experienced skipper will know when and where to go to avoid the winds. So, if you choose a skippered charter you don’t have to worry about it!


The best sailing itineraries in the Cyclades


Mykonos-Paros-Naxos-Small Cyclades-Syros-Tinos


This is an ideal sailing itinerary for seeing the best of the Cyclades from the comfort of your yacht. Not only are you going to visit the Greek superstar island, Mykonos, but you’ll also go off the beaten tourist trail in the tiny islands of the Small Cyclades complex. At the beginning of this itinerary, you’re going to visit Mykonos and Paros, two islands with a crazy party scene and a cosmopolitan flair. After getting your dose of crowds, you’ll continue with the less crowded islands of the Small Cyclades and with the elegant Syros and Tinos.


Paros-Naxos-Small Cyclades-Ios-Mykonos


This itinerary combines relaxation, exploration, and entertainment. Starting from Paros, which you can easily reach by air from Athens or by ferry from Rafina or Piraeus port, you’re going to sail to the nearby Naxos and the Small Cyclades, which are famous for their dazzling turquoise waters and rocky landscape. Next, you’ll continue with the final islands of the itinerary, Ios and Mykonos, which are go-to destinations for partying and socializing!


  • Kythnos-Serifos-Sifnos-Milos-Folegandros-Ios-Santorini
  • Milos-Kimolos-Sifnos
  • Mykonos-Naxos-Antiparos-Paros-Syros
  • Milos-Folegandros-Ios-Mykonos
  • Koufonisi-Amorgos-Schinoussa
  • Koufonisi-Donoussa-Mykonos


Sailing around the Saronic islands


The Saronic island complex is the best, easiest, and most popular option for a sailing trip from Athens, thanks to its proximity to the capital, ideal wind conditions, and calm waters. For these reasons, the Saronic Gulf is also a very good option for bareboat trips and cruises. However, there is a chance that the Saronic gets affected by the Meltemi Winds that blow in the Aegean and can exceed 7 Beaufort. This doesn’t happen often, though, and most of the time the winds are between 4 and 5 Beaufort.


The most popular islands of the Saronic island group are Aegina, Poros, and Hydra. Many yachts moor at the ports of these islands every summer to renew their supplies and their passengers often spend some days exploring the island’s villages and beaches.


The best sailing itineraries in the Saronic


Agistri-Poros-Porto Heli-Spetses-Hydra-Aegina


Following this itinerary, you’re going to see the best of the Saronic and the verdant bays of the Peloponnese peninsula. Departing from Athens, you’ll sail to Agistri to enjoy the island’s beautiful beaches and emerald waters. Then, you’ll continue your trip to Poros, a picturesque island in the heart of the Saronic, and Porto Heli, a cosmopolitan coastal town in the Peloponnese peninsula. Next, you’ll sail to Spetses and Hydra, the most elegant islands of the Argosaronic Gulf before departing to the final destination of your trip, Aegina.




This is a great itinerary for first-timers and for those who opt for a bareboat charter. Starting from Athens, you’ll sail to Aegina, Poros, and finally Hydra, the most cosmopolitan island of the Saronic. The distance between the islands is not very long, so you can sail to the next destination whenever you want.


  • Aegina-Poros-Agistri-Hydra-Moni-Ermioni
  • Poros-Hydra-Spetses


Sailing around the Ionian islands


The Ionian island group is another popular destination for sailing in Greece! Located in the western part of the country, this island complex is known for its verdant landscape and exotic beaches. Every summer, it attracts every kind of traveler, particularly youth and families.


Thanks to their proximity to the Greek mainland and the mild winds (usually up to 4 Beaufort), the Ionian islands are perfect for both skippered and bareboat charter. Corfu, Paxi, Zante, and Lefkada are the most popular sailing destinations for every type of sailor, even for those who have little experience. However, keep in mind that there are frequent rainfalls in the Ionian islands at the beginning of the summer and the beginning of fall. Our suggestion is to avoid these periods if you opt for a bareboat charter. If you have a skipper, though, he should know when the best time to set sail is!


The best sailing itineraries in the Ionian




Kefalonia, Lefkada, and Ithaca are three of the most beautiful islands in the Ionian Sea and a route that includes them is nothing less than idyllic! The first stop of this itinerary is Kefalonia, a verdant island with exotic beaches and many interesting places to visit, like the Melissani Lake and Drogarati Cave. The next stop of your trip is going to be Lefkada, which is perfect for snorkeling, and then, you’ll go to Ithaca, the mythical island of Odysseus.


  • Kefalonia-Ithaca-Zakynthos
  • Paxos-Antipaxos-Parga-Lefkada
  • Lefkada-Meganissi-Ithaca-Kefalonia
  • Lefkada-Paxi-Kefalonia-Ithaca


Sailing around the Dodecanese islands


The Dodecanese island complex is one of the most picturesque ones in Greece. Rhodes, Simi, and Kos are the most popular islands in the Dodecanese and also where most yacht charter companies lie. Thanks to their location in the southeastern Aegean Sea, close to the Turkish coasts, they are a very good base for sailing to Turkish coastal towns, like Bodrum, Fethiye, and Marmaris. The wind conditions in the Dodecanese island complex are mild (between 2 and 6 Beaufort), as the islands are protected from the north and south. That makes sailing easy throughout the summer.


What’s more, this island complex has many uninhabited islets to discover -it’s perfect for going off the beaten tourist trail! It’s also a popular destination for fishing, so if you are a fishing enthusiast, Dodecanese is your best bet.


The best sailing itineraries in the Dodecanese




This is a great itinerary for those who want to explore the most beautiful islands of the Dodecanese. The starting point of this sailing trip will be Rhodes, the Island of the Knights. In Rhodes, you can visit stunning beaches, stroll around the Medieval town, go sightseeing, and do many fun activities. The next stop will be Symi, the most picturesque and colorful island of the Dodecane. Finally, you’ll visit the volcano of Nisyros, the secluded bays of Tylos, and the little port of Chalki.


  • Kos-Leros-Kalymnos-Tilos
  • Kos-Pserimos-Leros-Lipsi-Patmos


Sailing around the Sporades islands


The Sporades island complex might not be as popular as the Cyclades or the Ionian, but it makes a great destination for sailing. Out of the 11 islands that constitute the complex, only 4 are inhabited, which leaves plenty of hidden spots to be explored and bays to stop at.


One of the main reasons why the Sporades is a top sailing destination is its proximity to the Greek mainland and the town of Volos. Another reason is that Sporades is not affected by the strong Meltemi winds that blow in the Cyclades. In the summer, the winds are usually between 4 and 5 Beaufort, creating the perfect conditions for sailing. Even when the winds get stronger, though, the waves don’t get big. Sailing in the Sporades is an ideal option even for less experienced sailors, as the islands are close to the mainland and close to each other.


The best sailing itineraries in the Sporades


  • Skiathos-Skopelos-Alonissos-Skyros
  • Skopelos-Alonissos-Kyra Panagia-Skiros
  • Skiathos-Skopelos-Alonissos-Kyra Panagia
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