Cyclades Island Hopping 2017

In 2017, I embarked on my first-ever island-hopping holiday in Greece, thanks mainly to my then-work-colleague (now close friend), Ed, with whom I shared a passion for the country.

Until then, I had only ever visited individual Greek islands for an entire trip. I had only visited the more commercial islands with international airports (think Crete, Corfu, Rhodes, etc). Following many lengthy and enthusiastic work conversations, we established that a joint expedition was possible. However, his limited availability meant he could only travel with me for the first four nights and would have to return to the UK on day five. On the other hand, I had the luxury of a break in my work contract, meaning I could travel for as long as I wanted, within reason. Three-ish weeks seemed about right, though, for a first attempt.

Ed had previous experience with the Greek ferry system, having visited many smaller islands while travelling. He’s also a passionate hiker. While I didn’t necessarily share all his enthusiasm for long walks in a hot country like Greece, any excuse to visit my favourite country seemed reason enough. I was assured of plenty of drinking, eating, and relaxing opportunities, so I happily deferred to him for the initial itinerary plans.

We settled on an outbound flight to Athens, connecting to our first island, Andros, via a ferry from the nearby port of Rafina. There, we would spend two nights, giving us a whole day to undertake an ambitious hike from the capital, Andros Town, back to the tourist resort of Batsi on the opposite side of the island. It should have been about 20 kilometres, but as you’ll see, it didn’t quite go to plan.

From Andros, we would work our way south to Tinos for a single night, then onto the famous island of Mykonos for another one-night stay. From there, Ed would fly back to the UK while I continued alone for the remainder of the trip. One night isn’t much time on any island, but we made the most of our brief stops on both islands, and it sowed the seed for the many future trips that followed and are documented on this website.

To avoid over-complicating my first solo itinerary, I took inspiration from Ed’s planning and continued south from Mykonos, visiting Naxos, Paros, Ios, and Santorini. With a few days left to spare, I decided to push on to the most southerly and largest Greek island, Crete, for the final nights of my trip, ending on familiar territory and with easy access to two international airports for my choice of flight back to the UK.

All of these islands, bar Crete, were new to me, though I’ve since revisited most of them at least once and, in some cases, many more.

This trip was incredibly memorable, inspiring my love of travelling around Greece. Read my first post here to get started.