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How to choose which Greek Island to visit on your next trip

Updated: Jul 6

In May, the National Geographic Traveller UK organised a Travel Geeks event called Plan the ultimate Greek island-hopping adventure and of course I was there to represent My Greek Island and share the wealth of knowledge I have acquired during my travels to Greece. One of the questions asked during the event was: "How do you go about starting to plan a holiday to Greece and choose where to go?"

If you were in the audience that day, you would have heard the tips I gave, so I decided to write this post for all of you who were not there and offer the information to the My Greek Island audience.

Greece offers a plethora of breathtaking islands, so how do you go about choosing which is the best one visit?

Greece is a country with allegedly 227 inhabited islands, each of which have their own unique character, making the list of islands a long one to choose from; Santorini is known for its scenic views and iconic sunsets, Mykonos for its whitewashed houses and nightlife, Rhodes for the medieval old town, Milos for its endless number of how do you go about choosing which one to visit, how to get there and when to go?

Below are some pointers on how to choose which island you should visit on your next Greek Island getaway. If you are a solo traveller, make sure to also check out the blog post: The Best Islands in Greece for Solo Travellers: Unleashing the Perfect Greek Escape.

And of course, don't forget to check out the My Greek Island Podcast available on all podcast platforms for dedicated episodes related to any destination of interest, where George and I expand in more detail. For ad free episodes and exclusive content sign up to the My Greek Island Patreon.

Island clusters and types

As previously mentioned, Greece has 227 inhabited Greek Islands, so to make things easier for you the Greeks have split them into clusters which are located near each other and tend to have similar characteristics. Whether it is the Ionian islands, the North Aegean islands, the Sporades, the Cyclades, the Saronic islands, the Dodecanese, Crete or Evia, within each cluster you will find large islands, iconic/popular islands, small islands and secluded islands.

Many people think of the Greek Islands and think of white-washed houses, hot tubs with a view and blue domed churches, but this does not hold true for all islands and is in fact seen mainly in the Cyclades.

So you can narrow down which island you want to visit if you check the island clusters and see which benefits each one has. For example, if you do want to experience the whitewashed houses and experience some island hopping, then the Cyclades is probably the island cluster for you.

Did you know: Greece is the most popular sailing destination in the world and a great way to visit many islands in one go and the most popular cluster to go sailing is the Ionian islands.

Transportation and Accessibility

After viewing the various clusters and narrowing things down, the next thing you will need to consider is how you will reach the island and whether you are willing to drive. Do you want to fly to directly, willing to fly via a main city in Greece, take a boat or combination of the above? Whatever choice you make, it is great that Greece can cater your requirements.

Many islands offer international airports, others domestic airports connecting to big cities like Athens and Thessaloniki, while others can only be reached via ferry from a main port or a neighbouring island.

Driving in Greece, and especially the islands is not for everyone. If you plan to drive, you could either rent a car on your island of choice or rent one in a main city and take it with you to the island. If however driving is not for you check out the blog post Exploring the Greek Islands; Top Destinations for Non-Drivers.

Do you plan to take a car with you from Athens of Thessaloniki on your trip? Check out our podcast episode with a local car rental company Cosmorent and sign up to our patreon (paid or free) to unlock the MGI Cosmorent discount code.

When to visit

The islands are most visited from June to August, with peak season being from mid-July to mid-August, although many islands enjoy long tourist seasons and offer activities off peak too, while other islands may not be fully functional for visitors beyond mid-September. To help decide when to visit, it is worth thinking what is most important to you. If its beach-time then you will probably want to visit during the popular months, whereas, if treks or other activities are more important, then it might be worth considering May or late September to early October.

Santorini for example offers great treks but also a vast list of wineries and museums so you could even visit until the end of October. To find out more about Santorini read the dedicated blog post Top things to do in Santorini and the MGI e-map with my top picks on the island.

Also, festivities in Greece are linked to the Greek Orthodox religion, so for example the15th of August and other festivities during the summer months known as panigyria to honour patron saints take place all over Greece. So it might be worth timing your trip with these festivities, as they can be great to participate in. However this also means there are increased crowds, so you would need to plan for visits during these times.


How long you plan to visit may help decide which islands are appropriate but also destination combinations. You want to be able to experience Greece to the maximum, without being overwhelmed. As a rule of thumb, bigger islands would require a minimum of 5 days and if you want to include the historic city of Athens during your stay, it might be worth combining with an island which makes sense from a cost, time and proximity point of view.

For those of you who choose to combine your holiday with the city of Athens, make sure to check out our dedicated podcast episode 48 Hours in Athens and download our corresponding guide (e-map) which includes all information mentioned on the episode and additionally some of my favourite things to do.

This guide can be downloaded for free using the discount code offered to all patreon members (paid or free)

Podcast Listening

The My Greek Island podcast is here to offer you information for many of your trips to Greece. Below are some episodes with links to Spotify, selected relevant to this blog post to help you plan and to inspire your travels more. Don't forget to check out the Bitesize Greek episodes to use some Greek words and phrases during your trip.

Book Me

Do you need help deciding where to go in Greece? Book a travel consultation session with me and I will help you narrow it down to a destination. Prior to the consultation, a questionnaire will need to be completed. During the session we will discuss the questionnaire and your needs and post the consultation, an overview of the destination proposed will be provided with key information and an e-map with places of interests and other tips and tricks.

Did you enjoy this post? If so, please leave a comment below and spread the love in the MGI community. And if you have a request for a specific post, feel free to get in touch!

Affiliate Disclosure: Some of the links on this website are affiliate links, which means if you book or purchase something through those links, I may earn a small commission at no extra cost to you. Your support helps keep the site running, and I only recommend products and services I trust.

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