Best islands to visit when sailing in Greece

Written by Samantha @Danielis on November 15, 2022 in Sailing Destinations

If you’re in search of long-lasting love, we can assure you that you’ll find it sailing through the thousands of Islands of Greece. You won’t just fall in love once, you’ll fall in love thousands of times with every island you visit. Who can resist white sand beaches, Cycladic architecture, and picturesque backdrops no matter where you go? Saying it’s Instagram-worthy is an understatement!




There is no better way to experience the wonders of over 3000 islands and islets than by getting a charter and sailing the deep blue Ionian and Aegean seas. But before you set sail in Greece, you’ll want to know the best places to head to and anchor.

Unless your vacation lasts a year or more, you probably won’t get the chance to see all of the Greek Islands. But that doesn’t mean you shouldn’t focus on trying to visit as many as possible for however long you are in Greece. Luckily for you, the majority of islands are in clusters, making it easy to hop from one to the next.

Let’s get into details about Greece Islands to see where the breeze will take you.

The Ionian Islands



The five main islands that make up the Ionian Islands are Corfu, Paxos, Lefkas, Kefalonia, and Zakynthos. All of which are located on the Northwest side of the Greek mainland. Given that these islands lean towards Italy you’ll be in for a lot of Italian-influenced scenery and Venetian architecture. Which island should you head to first? That depends. Are you more for spending the day anchoring in a bay, or do you prefer to head to land and explore?


This Island is a nature lover's dream, especially if you enjoy the greenery. It’s filled with beautiful mountains waiting to be hiked on, secluded beaches, small villages, and ancient ruins hiding between vineyards, olive trees, and pine forests.




Just off the south coast of Corfu, you’ll find the small island of Paxos, where you can anchor in the main port town, Gaios. On the tip of Paxos is also the town Lakka where you can find the two main beaches.




Out of all of the Ionian Islands, Lefkas is the closest to the mainland so you don’t have to sail too far. The most popular places to anchor here are Egremi Beach, Lefkada (the capital city of Lefkas), and Vlicho. Fun fact, Vlicho is so small it only has two roads, but luckily, it has plenty of seas to sail!


This beauty of an island is most known for its capital city Argostoli, which sits on a hillside where locals and tourists have a perfect view of anyone entering the harbor. So if you’re sailing into this port, make sure to wave to everyone that's shoreside!




Last but not least is the Island with the most photographed beach in Greece, Navagio, also known as Shipwreck Cove. You can also visit the Blue Caves located in the north of Zakynthos in Skinari, these caves are exclusively accessed by water.


In between all the sailing, walking, and swimming, you have to eat, right?

You’ll notice that Italian culture not only influenced architecture but cuisine too. While on the Ionian Island, you have to get a taste of specialty dishes such as Pastitsada, Sofritom Kefalonian meat pie, and some refreshing Corfiot ginger beer.

The Cyclades



In the middle of Greece and Turkey, you’ll find the Cyclades. Made up of over 2000 small islands and islets, of which only about 33 are inhibited. This is where you can embrace the island hopping experience. If you want a taste of the good life and pictures that will make all your friends jealous, the two must-visit islands in this cluster are Mykonos and Santorini. Given the popularity of these islands, you might also find yourself sailing by a celebrity or two, so keep your eyes peeled!


Must-have dishes that you can’t leave these islands without trying are Pitarakia, a specialty of Milos Island, Karpouzopita, and Ladenia (Greek-style pizza as some would say).

The Dodecanese



Due to the proximity of Turkey, in this particular area, you’ll encounter not only Greek tourists but also quite a bit of Turkish tourists, especially on Rhodes and Kos. If you’re a history lover, the Dodecanese Islands are made for you. Scattered across these islands are over 60 castles, medical architecture, historical gems, and exotic beaches such as Nisyros which is a black pebble beach located on a volcanic island.


Sweet or savory lovers will enjoy eating dishes originating from The Dodecanese Islands. Starting with sweets, make sure to try a special Rhodian treat known as Melekouni (similar to a sesame bar but yummier) and Akoumia. As for savory dishes, Kapamas and Spinialo are the way to go.

The Saronic & Argolic Gulf

If you’re situated in Athens the nearest islands for you are the Saronic Islands that extend into the Argolic Gulf. The main islands of Saronic are Salamis, Aegina, Agistri, and Poros.


Off the coast of Athens, the first island you’ll come across is Salamis, also the largest island in the Saronic Gulf. It is widely known for the Battle of Salamis which took place in 480 BC.


As you sail down south of the Saronic Gulf the next stop is Aegina. Whether you are up to the party, relaxing, exploring, or perhaps trying out some water sports Aegina Island has you covered. Some of the top attractions here are the Temple of Aphaia, Agios Nektarios Monastery, and Marathon Beach where you can enjoy Mediterranean dishes with fresh seafood.




After Aegina, you can make your way down to the island that many consider being an inspiration for writers and creative types. Enjoy a heartwarming romantic sunset at the top of a clock structure that dates back to 1927.




Between the Saronic and Argolic Gulf, you’ll find the renowned island Hydra. If you can describe this island in only two words it would be ‘classic beauty'. From the Piraeus dock, it will take you about two hours give or take to arrive in this paradise. Here you can visit Greece’s oldest pharmacy Rafalia, climb the bastions, or appreciate the architecture of over 300 churches and six monasteries spread across the entire island.

Argolic Gulf

Sail around the corner past Dokos and Idra to meet the Argolic Gulf. The Gulf in itself doesn’t have too many islands to visit but it’s worth docking into some towns on the mainland or searching for undercover caves and coves.


When life gives you lemons (or a lemon forest like in Poros), make lemonade, lemon cake, and everything lemon flavored. The Saronic Gulf is a lemon lover's dream. As for other foods, you will also want to get a taste of pistachios in Aegina, and almonds in Hydra.




This list would not be complete with the one and only Crete Island. What makes this island really stand out from the rest is that it’s not only the largest island in Greece but also the most beautiful no matter what time of the year you decide to visit. Given its diverse landscape, ranging from mountains to white-sand beaches you’ll feel as if you visited 10 islands in one.


Under any circumstances (unless you’re lactose intolerant) do not leave Crete without trying Cretan Cheeses. Such as Graveria, Kefaltyri, Staka, Mizithra, and the list goes on. Think of Crete as the Wisconsin of Greece! Also try to get your hands (or better said, taste buds) on some Mountain Bulbs (Askordoulakous), and Cretan Brandy for when the sun comes down.

The Cost of Island Hopping

How much you’ll be spending depends on what your budget is like and the areas you’ll be visiting. You might encounter an increase in price in popular tourist islands such as Santorini, Mykonos, and Crete. But generally speaking, prices in Greece don’t vary drastically and are still relatively cheap compared to other sailing destinations in the EU. Typically, sailboat rentals range from $220/day to $280/day, but this all depends on where you’ll find your perfect boat.

Important Note

Before you hop on board and start sailing you’ll want to keep in mind not only where you’re heading, but what the journey will be like while getting there. Given that summertime is the peak season for sailing it’s important to note that during this time first-time sailors or not-so-experienced ones should avoid areas such as the Cyclades, Dodecanese, and Saronic Gulf due to high winds, known as Meltemi.