What To Think About When Planning A Month Long Trip Around The Greek Islands

Travel planning is like decorating, it looks easy but it’s always so much easier for the professionals.


This summer I arranged a month long back-packing trip around the Greek Islands. If you’d like to do the something similar but ‘don’t know where to start  here’s a few tips that may help you get started.

You can also share my thoughts as I planned another ‘holiday of a lifetime.’

Travel planning is like decorating, it looks easy but it’s always so much easier for the professionals. Don’t be put off using a travel agent. They get a bad press but they know what they are doing. Even if you just talk through options and take away their brochures, you’ve learnt something.

You can just get online, right now, book a flight and start travelling. HOWEVER that may not be your best idea.

On a budget? Being impulsive may not be the cheapest option.

Have to stick to a set timescale? The ferry’s don’t run every day, so you could get stuck and miss your flight home.

Prefer to know where you are going? Plan it, or you may not see the islands you’d like.

For holiday planning I get a huge cheap notepad, nothing fancy and not a travel journal, not yet anyway. That comes later! Scribble down your ideas and date them. Things change, it helps you keep track. At this stage you are FREE to do whatever you want. Be creative and don’t rule anything out.

Try using the 5 W’s (+ 1 H) as I do.


My trip was just the two of us, which makes it simple. If you have seven kids and two grandparents, it’s going to affect your plans. Nothing is a problem, you may just have to accept limitations.


I’ll cover this later, but following surgery long haul wasn’t an option this year.


A summer chill out break, with a city break at one end or other. Probably.


I wanted four weeks away, but had a six to seven week window. If you can keep options on travel days and dates flexible it will help in finding the best prices on flights etc.

If you are restricted by day job, school holidays etc. it really is a good plan to book early. Look into when the school holidays and National holidays occur. If your trip coincides with local Saint’s days or similar it could make for an amazing trip with added extra celebrations. Or a nightmare of not being able to travel on shut down days. It could also mean accommodation prices are hiked up.

Greece and its islands can be hot, so if you don’t like it hot or are travelling with young children, consider going off season. This can limit choices of both accommodation and ferry crossings so you may need to cut down the number of islands you visit.


Life’s too short, and I wanted to see Athens. Also Greece was having a bad time in the UK media. The adverse publicity about refugees was affecting their tourism industry. Without wishing to sound patronising or naive, the Greek people had always been so friendly to me on past trips. I just wanted to help in anyway I could. 


Cheaply and flexibly, island hopping by boat. I knew my budget, which helped to focus things.


First job! Check out the government advice on travel for the intended destination.

This has previously resulted in a complete change of plan. I’m not paranoid, I don’t always trust the people in power, but I’m also not a total idiot. If the government say I’m likely to get kidnapped or hit by volcanic ash I’m going to take that on board.

Despite the media coverage all islands were deemed OK, just some advice about specific ‘trouble spots’ in Athens. I’d also watched the brilliant Simon Reeve programme which covered similar issues. Advice noted.

In the UK if the FCO suggests you don’t travel somewhere it may invalidate your travel insurance.

DO NOT travel without insurance.

No really, even just on a day trip overseas, ALWAYS get insured, it’s cheap compared to the alternative!

Check out travel forums, like Lonely Planet and of course keep an eye on the news. Subscribe to travel forum’s on Facebook or Twitter as well as online, keep informed.

Right then now on to the fun stuff, the details. Here’s how I went about it…


The travel industry is sadly built around couples, so two of us created no logistical problems.

If you are a lone traveller you have my sympathy as you may have to pay single supplements. The industry is gladly getting to grips with the ‘solo’ pound so dig around for bargains. Consider hostels, you will make lots of friends on the way.


Greek Islands, wow, never knew there were so many huh? Now on a globe they all look cosily close, they aren’t. It takes time to get from one to the next, so the best option can be to limit yourself to a specific island group.


Which islands?

I’d started out with an idyllic idea of getting out to the islands and moving around at will and when the mood took me. However, as I did some digging I soon realised this could be difficult. I had four weeks but that isn’t that long when you take off a day at each end for travel. A day to get from one island to the next etc.

So I needed to do the nitty gritty, read up on the islands.

I had to decide what I wanted to see, and importantly what I was willing to sacrifice.

I’ve mentioned in previous posts my 1 – 2 – 3 Plan:

1 – MUST DOs, absolutely on my bucket list.

2 – What I’d like to see/do, if at all possible.

3 – If I have the time and money, I’d like to include this too.

1 – Firmly in the MUST DOs was Athens. I’d studied it in my degree course and have never been able to afford it, now was my chance.

2 – I fancied Santorini, I knew it was pricey. santoriniMykonos was the cheapest option for flights home, and it looked fun.

Looking at the map it made sense to choose the Cyclades this time around.

greek-island-mapI have been to other islands on one off trips before, so this also honed the choice down. The world is so small and I have so many places I want to see, I try to only go somewhere once. No matter how gorgeous it is.


The Greek Islands, the perfect backdrop for a summer chill out. Some islands are livelier than others, as are some towns or cities. I wanted the city break in Athens, so knew I’d want a remote peaceful place to recover for a day or two afterwards.


I had a six week block, so did hours of trawling and clicking through flights, noting airlines, prices, flight times, baggage limits and stopover choices. Scribbling down all the options. It was at this stage I discovered that it was actually cheaper to fly home via Rome. Result!

Change the plan!

Include a two day break in Rome on the way home!rome-arch

I did say be flexible right? How about looking at air routes, it might be cheaper to do a stop over extension than a totally separate trip at a later date.


This question is the one I use to decide on specifics. I wanted to go to Athens, but why? I wanted to go to Santorini, but why? I read the tour guides and picked out various ‘mustn’t miss’ beaches, churches, antiquities, art etc. Be wary of taking on board too much advice from friends. Be brave. Whilst you may also love a place your mum suggests, you may love it for very different reasons, or not like it at all. It’s your trip, make your own decisions.


Once I’d decided on a rough idea of dates I started checking out flights. Skyscanner is my main source of initial flight information, I find them easy to use and they show good price illustrations.

In the UK a lot of the cheap flights go from London airports which for us Northerners can be really frustrating, however if you shop around early enough transport by coach / train to London can be reasonably priced. Why not check out a show and make it a mini city break?

Whilst the ferry network is comprehensive not all the islands are directly linked. Some routes are 6 – 7+ hour ferry journeys apart, which for me was too long. The ferry companies have great websites and apps. Despite numerous warnings about them not running to timetable, or indeed not running at all, we didn’t have one issue. It went like clockwork. The ferries were clean, arrived and departed to the minute and felt safe.

I’d been given an excellent piece of advice. Allow a day or two ‘just in case.’ If you are time bound e.g. By a return flight home, don’t miss it, make sure you arrive at your last island a day or two in advance.

It means you are not stressed, can wind down, do the final shopping for souvenirs or chill out in a beach side bar.

Travel Journal

Remember when I said that comes later? Once you have anything booked, pick up that very gorgeous journal and tactile pen, take the plunge and write down the detail.

I use the first few pages for the schedule, flights, etc. I then go from the back for accommodation. If it’s still a possibly/maybe then pencil it in.

This works for me:

Day 1 – Date

Travel plans (include flight times / seat numbers etc)

Overnight accommodation (even if it’s on the plane, write it down)

Activity (could be travel all day or beach or museum etc)

Day 2 – Date




(Don’t forget to leave lines spare for stuff you’re going to do on impulse. You get the idea)

I’m embracing the age of the smart phone but a paper back up is always recommended. Enter things in your email calendar, but remember timezone differences can create all sorts of confusion.

Still not inspired to DIY? A package deal could be your best option. All I ask is PLEASE, unless you have young children who demand ice cream all day, try to avoid the All Inclusive option. Spend money in local cafes, local shops and bars. Meet the locals, talk to them, immerse your self in the culture.

Waiting until last minute you may pick up a bargain package deal for two but more often, for your ideal break the sooner you start, the more bargains you can pick up.

So, back to the decorating analogy, it’s all in the preparation. I know, I hate sanding down woodwork too, but you know it makes sense. So does planning your holiday.

I hope you’ll let me know what you’ve got planned, and how you went about it and how you recorded the detail. My resources pages is a great place to start looking…

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Author: christieadamswriter.com

I’m a storyteller focused on sharing my love of literature, travel, photography and all things arty. My blogging supports my writing and I’m committed to encouraging others to pursue their dreams through travel and the arts.