A summer island-hopping adventure in Greece

My ‘big’ summer trip this year was supposed to be stateside to finally tick my final state of Hawaii off but it was something that needed to be planned and booked well in advance and when that point in time came, things were still very uncertain in the World as the pandemic continued to rumble on. Hawaii seemed a very big gamble when coming all the way from the UK – long haul flights, internal flights, car hire on multiple islands, hotels and condos all to book and while we could have gone through a specialist such as Trailfinders or Flight Centre to organise it all for us as a package giving us a bit more peace of mind should we have to cancel, we weren’t sure we’d get exactly what we wanted this way being so used to planning everything just how we liked it independently. It was a lot of money to lose should it all go wrong again.

So we begrudgingly made the decision to put off the trip another year and swapped Hawaiian island-hopping for Greek island-hopping. We knew we wanted to get out of the UK this summer as much as we’d enjoyed our UK National Park trips of the last two summers and Europe felt less of a risk than the US, somewhere we could easily return from mid-trip if needed, somewhere we didn’t need to test to enter even at our point of booking quite early into the year.

Wanting to island hop meant we still couldn’t book as a package trip. With flying in and out of different islands, we’d even need to book our main flights as separate bookings as the (mainly) package holiday carriers that flew there didn’t allow for open jaw bookings but we decided to go for it and hope for the best.

Having never been to Greece before, it was hard to know where to start. Who knew there were so many islands to choose from?! My friend who had been many years ago suggested Santorini and with this being an island in the Cyclades, we decided to concentrate on this area. After some googling, we saw lots of suggestions of mixing Santorini with a less ‘touristy’, more traditional island. Milos, Paros, Naxos and a few other islands I’d never heard of before all came up as recommended in various searches and we eventually settled on the much-praised Naxos island.

With those two islands only taking up a week of our 2-3 weeks available, my friends suggested looking into going to the ‘Mamma Mia’ island. She was a big fan of the film and wanted to visit some of the locations if we could. A bit more research lead us to find out this was filmed in Skopelos, one of the Sporades Islands and not really anywhere near the Cyclades! However, the neighbouring Sporades island of Skiathos was somewhere you could fly to directly from the UK and from here it was possible to do a ‘Mamma Mia’ boat trip to Skopelos. To get to the Cyclades from here, we’d have to fly via Athens and as neither of us had visited Greece’s capital city before, it seemed silly not to add a stop here into the mix!

Our trip was finally coming together – we’d fly to Skiathos for a few nights, fly to Athens and spend a few days there and then on to Naxos and Santorini by either plane or ferry – whichever worked out cheapest/least time-consuming.

With a few days still to fill, we looked at adding one more island. Wanting somewhere with plenty to do and some history behind it, I suggested the largest of the Greek islands, Crete. Being the most southerly of the Cyclades, it fitted perfectly into our into our itinerary as our last stop and with it being a popular package holiday destination from the UK, there was plenty of direct flights back to regional airports in the UK available, even one direct to Norwich, the closest airport to my friend!

Researching what we wanted to do at each of our stops, we carefully worked out how much time we’d need at each destination settling on a 2 night stop in Skiathos (just enough time to use our full day there on the Mamma Mia tour), 4 nights in Athens, 3 in Naxos, 3 in Santorini and 4 nights in Crete – a 16 night stay in total. After booking our main flights, we debated internal flights over ferries deciding by the time we added in time to get to the airport, checking in, collecting luggage after landing etc etc, a 4 hour ferry ride would be just as quick as a flight. For the most part, the ferries were cheaper too especially as we didn’t have to pay to take our luggage on board and it seemed like a more authentic option if we were island-hopping!

So, other than Skiathos-Athens where a flight was really the only viable option, we opted for ferries between the islands.

Accommodation-wise, we tried to stick with budget options, mainly using guesthouses or, with Athens, hotels in less touristy and therefore cheaper areas. Other than that, free cancellation was our non-negotiable and where possible, we tried to get some kind of breakfast included. Santorini was the main challenge here with many places being either already booked up for the summer or super expensive meaning we had to go above our £100 per night budget despite staying a 15 minute walk out of Fira town centre but we did at least have a hotel with a pool for that and we managed to save elsewhere.

Flights, ferries and accommodation sorted, we moved on to activities. With it being the height of summer, we knew Greece would be busy and wanted to save time by pre-booking tickets to museums and archaeological sites allowing us to skip the lines. We both decided that driving Greece would not be something we’d be confident with, especially with the language barrier, so instead we booked some organised tours on the various islands so we could still see as much of them as possible making sure, like we had with our hotel choices, that everything was cancellable until the last minute just in case.

In the run up to our trip, we began to wonder if we’d done the right thing booking such a short stay in Skiathos, mainly because of the airport disruption with airline delays and cancellations constantly in the news. Our flight already arrived relatively late into Skiathos, just after 7pm, and with just one full day there followed by a very early morning flight out to Athens the following day, any delays or worse, cancellations, would make our stay there pointless and possibly have a knock on effect on our transfer to Athens from there.

As it turned out, we were worrying over nothing. Flying out of the relatively small and quiet East Midlands Airport and with Jet2, possibly the least disrupted UK airlines this summer, was a good decision. Everything ran smoothly with our departure and before we knew it, we were arriving into Skiathos ready to begin our summer island-hopping adventure in Greece!