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How to Plan the Best Greek Island Hopping Holiday Ever

With 7 Easy Tips & Example Itineraries

February 6, 2020


This time

around two years ago I created and organised a whirlwind island hopping

itinerary to some of the major (and some lesser known) islands in Greece. In

the space of only 11 days we travelled to up to 4 different islands as well as

to Athens on the mainland. Although

the time it took to research all the different and wonderful islands in Greece,

the things to do, how to get there, where to stay etc. probably took just as

long as the trip itself; we did at least narrow down on some key points which

helped make our search a lot easier and I will be running through them in this

article by asking you a series of questions.

Alice Ogeh


A Lawyer in her previous life, the copious hours of scrutinising law text books, case law and wikipedia have resulted in the birth of a creature, whose capability to research into the paths less trodden, surpasses most seasoned travellers.

1. What Do You Want to Do?

First and foremost you need to know exactly what is that you want do and what it is that you're interested in. While we don't want to over-generalise each island as most islands have something special to offer for travellers of pretty much all tastes, in our opinion the islands can be grouped into the following categories:

  • Party Goers
  • Sunsets & Romance
  • Watersports
  • History & Culture
  • Spa & Relaxation
  • Best Beaches
  • Families
Party Goers

Mykonos, Ios, Zante, Kos, Rhodes, Cyprus

Mykonos is usually seen as one of the most expensive island to party at (for good reason too - one cocktail can set you back €11), whereas Ios is usually seen as a cheaper option - just beware anyone who is 30+ years old, as it's mostly college/university students that frequent the island of Ios.

Sunsets & Romance


When it comes to postcard perfect views, there is one clear winner - Santorini! One of the top destinations for honeymooners, it's no wonder that the sunset views are enough to make your heart melt.


Paros, Naxos, Crete, Lefkada

Calling all REAL adrenaline junkies , we repeat all REAL adrenaline junkies! While most Grecian islands can offer some form of water sport, whether it be jet skiing (if you call that a sport) or water skiing, the real water spot action is to be found in the windier islands of Greece, like Naxos, Paros and Lefkada.

History & Culture

Paros, Skyros, Hydra, Rhodes, Athens, Delos

Athens probably being the most accessible site within Greece for historic artefacts (new artefacts are still being found daily!), we would still highly recommend any history buff to travel further out to islands such as Delos, an island which is one of the most important mythological, historical and archaeological sites in Greece.

Spa & Relaxation

Santorini, Athens, Pella, Kos

Santorini is well known for its boat cruise and volcano tour which takes you to a natural hot spring; however, Greece is dotted with several hot springs, natural spas and other natural phenomenon which will have you relaxing in no time.

Best Beaches

Kos, Santorini, Paros, Naxos, Cyprus , Zakynthos , Corfu, Rhodes, Kefalonia

The pictures say it all really.


Corfu, Crete

With direct flights from the UK, these two large islands ofter a convenient respite for families looking for resort type fun. Although these islands have previously been popular with Brit hen parties and stag dos, both islands are large enough that whole sections of seaside have been pretty much dedicated to family resorts.

2. What Is Your Budget?

The difference between the cost of a margarita on one island compared to the cost of a margarita on another island may be enough to make your head spin. The same goes for accommodation, excursions and even transport. Most often than not the variable prices have nothing to do with the level of sights  or beauty that can be found on the islands - most if not all Grecian islands really are beautiful beyond comparison. Its more to the do with the type of tourists that frequent the island especially during peak seasons. 

Mykonos has by far some of the most expensive prices for food, accommodation and drink when compared to other islands and given that it's mostly millennials and gay partygoers with surplus cash that frequent, it's no wonder that the island can command such a price. In comparison, we were able to pick up a full meal in Naxos for just over €5 per person. 

3. How Bougee Are You on a Scale of 1-10?

For a group which we knew we would be moving about quite a bit as we were more interested in exploring our surroundings, the accommodation wasn't so much our key focus. Outside of Athens, Mykonos (to an extent) and Santorini, the accommodation types on offer across most islands tend to be very similar. Self catering  apartment or room styles with the usual off-putting hotel colour schemes (why orange and green??), private bathroom and fridge at the very least. 

If you're looking for more luxury accommodation, like rooms that lead to their own infinity pool and the such, islands such as Santorini, Mykonos, Rhodes and Cyprus are likely to have a much greater variety to choose from.

4. Suffer From Sea Sickness?

Although some islands do host their own airports with flights coming in and out from Athens, the key feature and convenience of island hopping is the fact that you'll be travelling by boat, or to be exact in the case of Greece, the very efficient and reliable ferries. Even though we visited in peak season it was fairly easy to purchase our ferry tickets a day or two in advance from local tourism shops and offices.

For those worried about sea sickness, you may be happy to hear that you feel very little movement at all, even my friend who suffers from very terrible sea sickness was fine for the ride from Athens to Paros (our first stop) without any sea sickness tablets.

Once you're off the ferry and have arrived at the port of the island, some islands were so small that it was possible to walk from the port to our accommodation, others we just took a taxi or arranged pick up from our accommodation. If you haven't arranged any accommodation before arriving at the port (which is totally possible to do) you don't have to worry as there's normally plenty of accommodation providers with last minute rooms available waiting at the port for arrivals and you tend to get the rooms (because its last minute) at a bit of a discount.

5. Have You Checked Ferry Timetables?

Another thing to bear in mind when it comes to transportation which also relates to the second to last point, is the timetables for the ferries. Some ferries do not operate everyday and so when planning the logistics of the holiday ensure to leave a gap of at least one full day on either side of your first arrival inGreece and departure from Greece.

You can check for up to date ferry timetables and costs HERE. Although estimated costs are shown in the picture below, please note that in reality our tickets were a lot cheaper and the map also assumes that you will be taking taxis etc. to reach the port, so take a look at the costs below with a grain of salt. Note that if you're landing in Athens there is a direct train from downtown Athens (Monastiraki station) to the Piraeus ferry port. It takes about 20 minutes from central Athens to the ferry port.

6. How Much Time Do You Have

Most of the islands of Greece can be grouped into about 5 or 6 groups/areas by their proximity to each other and shared characteristics. Knowing the different types of groups/areas and comparing that to what you are looking to visit in the time that you have, will probably be the single-most important thing to consider.

I have set out three of the easiest and some of the most popular routes to navigate below, which you can cover a period of a week or longer.

  • WEST
  • EAST

Ionian Islands - Corfu, Lefkada, Kefalonia and Zante

If you land in Corfu and you would like to visit some nearby islands, one of the easier routes is via Lefkada, Kefalonia and Zakynthos with your exit flight coming out of Zakynthos, with a stop over at Athens for the more budget airlines, or you can fly direct into London Heathrow (normally slightly more expensive).


Cyclades Islands (popular for island hopping) - Mykonos, Santorini, Paros, Naxos

For a straightforward route which can possible finish up within a week, once you land in Athens, you can then take the ferry to Paros (you can also do a day trip to Antiparos from here), then Naxos which is very close by, then decide whether to head on to Mykonos or Santorini, or if you have a longer stay (like two weeks) you can do both.


Dodecanese Islands - Rhodes, Kos, Symi, Patmos, Samos

A less frequented island hopping tour is via the most popular Dodecanese Islands. Most Brits are happy with catching a flight out of the UK to just one of these islands once a year, but why settle for one, when you can tour 4 and through in a stop over in Turkey for good measure due to the close borders. You can get direct flights to London from airports located in Rhodes and Kos and an indirect flight from Samos, stopping over at Athens.


The Aegean Islands - Icaria, Kos, Samos, Chios

This is a route for those that are really intrepid as it does take you quite a way from Athens to get to the first stop Icaria, which depending on the rates at the time of booking, it may actually be cheaper to take a flight out of Athens to Icaria than a ferry, which will require a stop over at Syros. Although the route may seem daunting, the views and untouched nature make the journey well

worth the time. For your exit strategy you can actually flight out of most of the islands, just bear in mind that all flights will require a stopover at Athens and sometimes the stopover can be overnight.

If you like what you've read so far, ways you can support us is by following and engaging with us on social media, getting your friends to sign up to our email newsletter (gain a £5 reward to spend on our itinerary services and upcoming group travel collaborations for you and your friend) and be one of the first to test our new website once it launches! We love you and appreciate all the support.

7. What is Your Exit Strategy?

Most people when planning an island hopping holiday seem to forget the last little detail - how are you going to make it back on time for your return flight? Luckily a lot of islands across Greece do have their own airport, but most flights tend to have a stopover in Athens before . In most cases it would be more economical to ensure that your itinerary is planned in such away that your last stop is an island with an airport, as opposed to just a ferry port as it tends to be quicker and cheaper to get back to Athens via plane than it is

ferry. Consider this, in planning our itinerary visiting some of the Cyclades Islands, I found that we saved close to £120 just by opting for open jaw flights for our departure and return, as opposed to a standard return flight from Athens, meaning we would have had to fork out close to £80 at the time and almost 7 hours of a ferry ride just to get back to Athens from Santorini.

If you need help planning your island hopping itinerary across Greece, don't hesitate to get in touch with our Expert Connects.

If you like what you've read so far, ways you can support us is by following and engaging with us on social media, getting your friends to sign up to our email newsletter (gain a £5 reward to spend on our itinerary services and upcoming group travel collaborations for you and your friend) and be one of the first to test our new website once it launches! We love you and appreciate all the support.



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Not to worry, you can always come back to us later, but while you're figuring out where to jet off to next, you should at the very least save some coins and time, while doing it.

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