A Go-To Travel Guide to the Greek Islands

Greek Islands

The Greek Islands 101.

Surely, you are here because, well…its been on your mind. Let me guess- it’s even on your bucket list. I know, I know. Greece has a way of capturing people and leaving them completely breathless. Yet the biggest question is, where do you start? How do you start? Well, let me see if I can help you. This is a preliminary Greek islands travel guide.


Me at the Acropolis in Athens.
The Acropolis of Athens

Now personally I had not had a chance to fully explore mainland Athens as my focus had been the Greek islands, however, in a place as rich in history as Greece, Athens is not to be missed. For example, the Acropolis is certainly a sight to see, but I’ll get more into the details in another post. With that, let’s get you in order for your trip to the islands of the gods!

A bit about the islands

First off I will tell you that Greece has roughly 6,000 islands, with only 227 being inhabited. Wheew, those are big numbers! However, that means you have more than enough legroom to pick and choose which islands fit your fancy, provided that you understand how to navigate around. To make it a bit easier, the islands themselves are divided into groups ( For simplicity, I have included the major and most inhabited islands of the groups; the latter 3 being proper islands).

Amorgos, Anafi, Andros, Antiparos, Delos, Ios, Kea, Kimolos, Kythnos, Milos, Mykonos, Naxos, Paros, Folegandros, Serifos, Sifnos, Sikinos, Syros, Tinos, and Thira or Santoríni

Corfu, Paxos, Lefkada, Ithaki, Kefalonia, Zakynthos, and Kythira

Agathonisi, Astypalaia, Chalki, Kalymnos, Karpathos, Kasos,  Kastellorizo, Kos, Lipsi, Leros, Nisyros, Patmos, Rhodes, Symi, and Tilos

 Salamis, Aegina, Agistri, Poros, Hydra and Dokos

Lesbos, Chios, Psara, Oinousses, Ikaria, Fournoi Korseon, Lemnos, Agios Efstratios and Samos

 Alonnisos, Skiathos, Skopelos and Skyros

The largest of the Greek islands

The second largest of the Greek Islands

A peninsula in Southern Greece

How I did it

When I decided to head to Greece, I was planning it around my birthday, which is in July. Now, mind you early May and into October are possibly the most ideal times to visit. The high season, which is the season EVERYBODY is in Greece, is pretty much June-July. With that comes exorbitant prices for flight tickets and accommodation. However,…there is always a way around it. The key is in the planning.

Locations, such as the Greek isles really require advanced tickets. For example, if you were to plan a trip in June, look into purchasing tickets around the month of October the year before. As crazy as the high season can be, I won’t lie to you, it is a beautiful period to visit.

You are going to want to find flights heading straight to Athens first, as this is where the major international airport is located. From Athens, you can easily get a connecting flight to most of the islands. You even have the option of taking ferries. I’ll get into that a bit later.

Finding tickets

So, where do you purchase tickets? I love my travel hacks. Haha One great site that you can always use as a reference is Hopper. It is a cellphone application that really and truly is fantastic because it allows you to look into the best months to travel, well in advance. Although you cannot actually purchase the tickets through the site, it can redirect you to the affiliated websites to make your ticket purchases. Some other great features are that you can book hotels, cars, or even freeze prizes. Hopper serves as a great guide to tell you when to buy.

Now, on to my two all-time favorite sites for searching for tickets: Skyscanner and Kayak. Many people use these two websites mainly due to their ease in search-ability. They have even saved me quite a few times on some last-minute trips. When I say “saved me,” I mean a trip that would normally cost between $600 – $1200, I managed to get for $200 round trip. Prices change frequently throughout the day, so just stay ready! What you really want to be watching for are…flight ticket errors. These are basically errors in the ticket price. Believe it or not, you will find this occur often, so just check the websites periodically throughout the day.

Getting to the Greek Islands

So, how do you get to any of the greek isles? First off, you better choose which islands you want to see!

The thing is, when selecting which islands you want to see, you must be strategic. It is very difficult to navigate between islands (although there is one particular exception which I became familiar with). So, say for example you really want to see Santorini, you have to take into account that Santorini is in the Cyclade family. Thus, if you want to visit a few others, for the sake of ease and mercy on your wallet, stick to other islands within the Cyclade family.

I really wanted to visit three islands, and I had two weeks to make this happen. So the first island at the top of my list was Santorini, since you know… it’s the talk of the town. The next island I chose was Milos. I was so intrigued by this island due to the fact that it is the birthplace of the goddess Aphrodite. It is also a Cyclade, so an excellent bonus.

Boat riding smooth in Milos, Greece
Milos for the taking!

Now, here is where I was a bit stuck. I was yearning for a simple and authentic Greek experience. Not that the other islands don’t offer equally beautiful experiences, but I wanted to really feel the Greek experience, and delve into a bit of history at the very same time. Most importantly, for this portion of my trip, I knew I was going to be alone, so I wanted to really brace myself for a true adventure. I spent quite a few weeks doing research and fell upon Crete. It is the largest of the islands, but that was not going to stop me. I planned Crete, just as well as the others.

To fly or sail to the Greek Islands

First thing you will want to do is fly into Athens. You could spend a few days there, or you can immediately book your connecting flight to your first island. I did the latter. For flights around the Greek isles, you will most likely fly Aegean airlines. I found their service to be quite good. Actually, I loved it so much, I joined their loyalty program.


I chose to fly to Santorini first, because it is a major hub and very well connected. Once you are there, you can easily get to the other islands. It is convenient to do so by ferry. With Santorini as my base, I took a ferry to Milos, for a day trip. I then took a separate ferry from Santorini to Crete. Although both trips are generally quite comfortable, the ferry to Milos was a bit scary.

Purchasing Ferry Tickets

So I’m the kind of traveler who loves options! It just takes me forever to choose. Haha When it comes to purchasing ferry tickets, it might be ideal to do so in advance. There are three websites I found quite helpful: petas.gr , danae.travel , and Ferriesingreece . Offering a variety of features, all three will can be searched and booked in advance for whichever island it is you want to see- given that the islands are within the same family. Ferriesingreece even provides an “island-hopping” option to help you further pre-plan.

Ferriesingreece website example to optimize planning your trip to the Greek islands.
Pre-planning your island-hopping.

Oh and one more thing I will suggest…TRACK YOUR FERRY! I found on a few of these trips, the ferries can sometimes be really…really delayed. It can be quite an inconvenience if you only planned on doing a day trip, with plans back at your home base afterward. Therefore, it is probably best to plan on spending the full day at the location to make the best out of your day trip. A great website I used to track my ferries was: My Ship Tracking . It can actually be used to track ferries in different countries, has the ability to provide real-time tracking, and has a free downloadable app for iOS devices.

An example of real-time tracking with My Ship Tracking .


As I had mentioned, Milos is Aphrodite’s island but it is also referred to as the windy island, and for good reason. Leaving Santorini, the waters will be calm, but rest assured about 15-20 minutes into your ride, the boat will start to rock. Some might think this is fun, but I for one, was shaking the whole time. It gets worse at night when you are going back, so just hold on to your seat.


As for your ride to Crete- it will be very smooth. To be honest the boat they used kind of looked like a luxury cruise line. If I recall well, I had a reclinable seat, my own tv, and the food was exquisite. This was all included in one very affordable price. So trust me as I say, this leg of your trip will be a piece of cake!

For more details on my experience on the individual islands, check out my other blog posts. I go into a bit more depth regarding places I frequented and things I did. Hope you enjoy!

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