How I plan my Greek holiday

How I plan my Greek holiday

How I plan my Greek holiday? Well, many people use a tour operator to book combined flights and hotels with a rep. I used to and not saying this is right or wrong. However, many tour operators don’t offer odd number of nights like 9,11 or 12.

Also, because we often like to see more than one Greek island, ferries have to be factored in too.

Besides which, I love the planning of a holiday, myself

So this is how I plan my Greek holidays, when looking at island hopping.

Location often decided a year or more in advance. Using Goggle maps and explore Greece and then my chosen island. If I want to see other islands in the same area, check whether ferries go from one to another.

Whats to see and do?

Next, I look at what kind of attractions are there to see and do on each island. We love to go off exploring to see windmills, churches, waterfalls, beautiful coves and scenery.

I look at the island that has the nearest airport. Using this as a base to start and end with. Once decided on a Greek island that I can fly in to, I decide how many days going for. In addition to how many islands could potentially fit in, close by.

As an example:

So for arguments sake, as an example, lets look at Kos and Nisyros, Leros and Kalymnos islands, in the Dodecanese area of Greece.

A year in advance, decided to look at how to do these 4 islands together, for a stay of around 12 days.

Kos has an airport from which flights from the UK go to. I checked out ferry companies that would take us to the other 3 islands.

Google maps has been instrumental in my planning

Usually you can zoom in on Google maps and look at the port area for each island and there will be a dotted line telling you that a ferry goes from island ‘A’ to ‘B’.

A word of caution: ferry schedules are not available that far in advance, so I look at the current year,  as a rough idea, to see ferries- what days and frequency. So I found out Dodecanese Seaways and Blue Star ferries go to these islands.



Reckoning 2-4 days would be more than enough on each.

Using my usual way of booking hotels- Because we are island hopping and need to be close to Port for getting from one island to another, it made sense to find hotels in these areas.

Like because if book early enough you can get a good choice of room accommodation and often reserve now/ pay at the property and free cancellation.

Flights and travel insurance

Thus, I reserved rooms for Kos, Nisyros, Leros and Kalymnos. Then sorted the flights separately [using sky scanner or typing in on Google ‘who flies to Kos from the UK?’] for operator, price and times to suit us.

Generally speaking for Greece, Tui, Thomas Cook and EasyJet, I have flown with.

Subsequently, I then booked our flights [ they usually ask for full payment for flight only]. I also then sort my Travel insurance.

I am a nerd- Have an itinerary

Next, I start by planning an itinerary. What to see on what days, where we could explore- how we are going to get there. Car, ATV, bus?

I spend a vast amount of time online reading other peoples reviews [ namely, on Trip Adviser] and tips for where to go. I also zoom in on Google satellite maps and Street maps if available.

Checking ferry timetables

As the time gets nearer, keep checking the ferry operators to see when the ferry schedule is out. When booking this holiday, I had everything booked except for the ferries.

Then found out on my first itinerary that my dates/hotels/islands didn’t line up with ferry schedules as they didn’t go to all islands every day.

So I had to do a quick reshuffle of the days on each island, change my dates on [ luckily they had availability and remember, I had free cancellation, so no charge for changing dates] and then able to book the ferries over the internet.

An example of my itinerary:

So a sigh of relief when all the ferries were booked. So in the end, this is how I plan my Greek holiday:

Day 1-Fly to Kos-taxi from airport-Stay 1 night-Early ferry [ Sunday] next morning from Kos to Nisyros.*

Day 2-Nisyros-exploring with ATV Pali/ Emporios/ Nikia and other places on way *

Day 3-Nisyros-explore Stefanos Crater on volcano/ Mandrakia -evening ferry to Kalymnos *

Day 4-Kalymnos- car-explore Myrties/ Masouri, small boat to Telendos island

Day 5-Kalymnos-explore Vathy-mountain road to Palionnisou/ Arginonta/ Emporios

Day 6-Kalymnos-explore Chora castle, Vlychadia, and Savas monastery

Day 7- ferry from Kalymnos to Leros-explore around Lakki area

Day 8-Leros- explore by car-Blefountis beach/ Ag Isidoros church on causeway/ Agia Marina

Day 9-Leros-explore Windmills/ Castle and Panteli beach

Day 10-ferry Leros to Kos-stay 1 night around port area

Day 11- Kos hire car sight see a couple places and stay night in Kardamania

Day 12-Kardamania -Kos waterpark and drive to airport for flight home, evening

2 ferries booked were with Blue Star and 2 ferries booked with Dodecanese Seaways.

* However, unforeseen circumstances can change plans in a blink of an eye. Immediately, I had to put a plan in to action.

Four days before departing for Kos, received an email from the ferry company to inform me that the Kos to Nisyros ferry departure would be changed to 18 hours later than planned. In other words, now leaving at 01.00am on the Monday morning from Kos to Nisyros.

What good is that when our ferry from Nisyros to Kalymnos is on Monday evening? As you can see from the first 3 days of the itinerary, that would mean only a few hours stay on Nisyros.

A pat on the back for me- got it sorted

After a frantic call to the ferry company in Greece, explaining my predicament, gave me a number to call. Called a local man who told me that a day trip boat was leaving Kardamaina on Sunday at 09.30am to Nisyros.

‘Off shore travel agent’

Ferry company refunded our fare after we declined their later schedule. On the Sunday, had to book a taxi to take us to Kardamaina where we found Off Shore travel and purchased one way tickets to Nisyros for 8 euros each. The crossing was around one and half hours.

As planned, the ferry on the 2nd evening to Kalymnos ran to time. Phew.

Purchasing ferry tickets online

Usually when paying for ferry tickets online, pick them up at the port and the email confirmation tells you where to collect them.

The first time I ever planned an island hopping trip, I sat in the UK booking ferries hotels etc I kept thinking will everything work when we get there. So far, I have had no hiccups, everything has gone smoothly and I always pat myself on the back after thinking it all worked out well.

Island Hopping adventures

Moreover, we have successfully island hopped from Mykonos [ used as a base and most nights spent here] to Naxos for 1 night and onto Paros for 1 night. Ferries used were SeaJets and Blue Star.

Also flown in to Santorini and then SeaJets ferry to Milos for a 5 night stay before returning back to Santorini for flight home.


Always ensure you leave a good day or two to get back to the island you are flying out of, just in case of any cancellations with the weather and the ferries.

Also look to see if there are any local ferries or boat trips to other islands. So for example, when staying in Corfu, I now know that Kamelia lines do a daily ferry service to Paxos, from which you can get a sea taxi to Anti Paxos.

Ferry carriers

On Milos island a local ferry called Panagia Faneromeni runs every 30 mins or so from Pollonia to neighbouring island of Kimolos. Taking 30 minutes to get there.

Anes Ferries go from Skiathos to Skopelos, as do Hellenic Seaways Flying Cat 5.[Cosmote]

If you need advice on ‘how to plan a Greek holiday’  am happy to try and help if I can.

I am not an expert, I can only advise what we did with our experiences.