Preparations for an Island Hop with the Fam!

The ‘idea’ of this holiday has been over 2 years in the making. Originally planned as a trip with one of my granddaughters who had just turned 16 as a way to celebrate the end of her exams. No sooner had the flights been booked, the dreaded Covid struck and all our plans went up the wall. I had booked flights to Athens and the ‘idea’ hadn’t really progressed further than that – purposefully. I wanted to show my granddaughter how to island hop by making it up as you go along – ‘old school stylee’. Except maybe without the rucksack. I’m too old and decrepit to be carting luggage around on my back!

Now we are back to some kind of normality where travel is concerned (well almost!) the ‘idea’ is back on the table and our travelling party has expanded somewhat. With granddaughter now 18, I will now be joined by my husband and two other grandchildren aged 14 and 17 which I’m very excited about. I’ve had to re-think the plans though. We are now travelling mid July and already in my day job I’ve seen hotels in Greece getting booked up quite early on in the season. 2022 is an absolute bumper year for Greek travel which is fantastic news for the travel industry. This trip has been thoroughly planned with all accommodation booked beforehand – something quite novel for my own personal travels.

So where to this time? The grandchildren haven’t been to Greece before – they’ve been to far flung places but never to Greece so I feel that it’s my duty to show them some of what the country has to offer. Think of Greece and what do you see? I think that picture postcard image of Greece is of the white cubist buildings and blue domed churches, so to give them that experience – the Cyclades it is!

I also have to consider that 3 teenage children may not ‘yet’ appreciate being taken off the beaten track and would possibly want something a bit more lively so hopefully this itinerary will show them a little bit of that.

The best value flights for our dates was to Santorini. Santorini of course along with Mykonos are two great gateway islands that bring you into the heart of the Cyclades. To be honest Santorini is not my first choice of island to spend much time on primarily because of how busy and crowded it gets. However, the island has many spectacular assets, some of which I know the grandchildren will love. One of my granddaughters will be going to university in September to study geography so a visit to the volcano is an absolute must.

I’m sure that all seasoned island hoppers have their own preferred ways in which to plan an itinerary and I definitely have my own style and it usually starts with a map. I have a large framed wall map of Greece next to my office desk for easy reference. Above my desk I have an array of Greek related items almost shrine-like peering down on me. I’m a visual learner and communicator so tools like maps are invaluable to me. I’ve also been known to scrawl on map printouts and even spread out a large sheet of paper on the floor and draw a route this way. The latter is usually for my own, more complex itineraries.

My next step is to put everything into a spreadsheet. This is really handy if you want to keep an eye on costs. I’ve started costing up my itineraries before, during and after travelling and then posting that information in the blog. This may be useful for other budget travellers.

I already have an idea of the islands that I think would make a great itinerary for the family. Thinking of the islands that are easily accessible from Santorini, I know that Naxos is an absolute must. As far as I’m concerned Naxos really does have it all – beautiful golden sand beaches, an atmospheric kastro quarter and charming mountain villages. It also has a very good bus service that will get you around the island quite easily.

When planning an island hopping trip the first thing I always determine is whether the route will be circular or linear. The very nature of the ‘Cyclades’ is that most routes (but not all) will be circular. The name Cyclades means ‘encircling islands’ as the islands encircle the sacred island of Delos just off the coast of Mykonos. This is different to planning a trip to the Dodecanese for example where it is likely that your route will be linear.

Both routes are relatively easy to plan – a circular route should bring you back to your place of arrival/departure (assuming that you’re flying out of the same airport that you arrived in). With a linear route I’d usually go to the furthest island first and then work my way back to the arrival/departure island. With this approach you are always making your way back to where you need to be to catch your flight home. With all of this in mind, of course the skill is in making sure that the ferry connections will be amenable to your plans. There is no hard and fast rule to planning an island hop but this is the rule of thumb that I usually apply.

Talking about the island groups is an important point. The ferry lines tend to run within or along certain island groups i.e Central Cyclades, Dodecanese, Eastern Aegean. Of course there are others that cross island groups but a basic knowledge of the various ferry lines is useful when planning an island hop. Back in the day the island hoppers bible was Greek Island Hopping by Frewin Poffley – a Thomas Cook publication. I have various editions that I’ve used over the years but of course this was all pre the smart phone era. The book was chunky – and I mean chunky! The books consisted of over 600 pages of information. They were so thick and heavy that I used to press a flower in between the pages of each island that I visited. If you can get hold of an old copy it makes good reading although some of the ferry information will be out of date.

My first itinerary didn’t quite go to plan. I’d sketched out a route with all known ferry connections in March. The only ferry connections that I didn’t have was from Santorini to Sikinos. However, I’d read that during summer there is a daily service. Looking at the previous year’s schedules this seemed to be the case so it gave me the confidence to book hotel accommodation for us all as well. When the Santorini/Sikinos schedule did finally get published at Easter to my utter dismay, the only day that the ferry wasn’t going to run was the day I’d planned for us to go! Back to the drawing board I went to make further tweaks so that the itinerary would work.

In most instances if not all, we will be staying in slightly better accommodation than I would normally. As a budget traveller my main requirement is a clean room and air conditioning after all the hotel or pension is just a place to lay your head. For me it’s always about the location rather than the accommodation as I come to explore a new destination – not the hotel. Yes I’ve stayed in some really nice hotels in Greece but I have always preferred smaller family run establishments rather than the more sterile larger chain hotels. But that’s just me. I’d rather stretch my purse to allow more trips rather than have upgraded accommodation.

Anyway, although I love planning itineraries and do it almost every day, I’m sure me rambling on about it doesn’t make good reading material.

The itinerary that I have planned for this trip is below. I think that this is the perfect itinerary for my family’s first trip to Greece:

Santorini 1 night

Sikinos 3 nights

Ios 3 nights

Naxos 5 nights

Santorini 2 nights

This really is going to be a whistle stop tour! When I do my solo trips I much prefer to spend longer on each island. You’ll never really get to know an island inside and out as a visitor but at least a longer stay will enable you to have more of a sense of it. That’s maybe something to do with the awareness of my age and own mortality. I know that in the past I’ve done what I call a ‘hit and run’ on an island and have said that I can always go back. In reality we don’t always go back and I remind myself that Island hopping in Greece isn’t a tick box exercise. It’s an experience.

Anyway 2 weeks to go and all fingers and toes are crossed that everything goes to plan. I hope that this trip gives my gorgeous grandchildren a taste for this beautiful country and that they all have the most amazing time!