Western Cyclades 2020: Trip Planning Overview

Wednesday 5th August 2020

Introduction

So, it’s that time of year again. Except that 2020 has been anything but a typical year, with the Coronavirus pandemic locking down most countries from March – July and along with it my 6-week trip to New Zealand in April/May was cancelled. Oh well, best-laid plans and all that…

It’s a funny feeling not having been on holiday at all this year – obviously an insignificant concern compared to the death and suffering caused by the virus, but for me personally it’s an unusual situation and one I’m keen to rectify. On July 15th, visitors from the UK were allowed into Greece again, albeit subject to random testing on arrival with the potential to be quarantined on a positive test result.

Back in February, Ed and I had made plans for a short break in mid-September, with Ed going as far as booking flights and accommodation. I held off booking as I wasn’t sure what my finances would look like after the New Zealand trip. Given the situation now, I have the money and holiday time at work for a longer trip instead so my plan is to head out earlier in the month and link up with Ed when he arrives on the 16th.

In Search of New Destinations

After the usual dilemma of whether to visit the Cyclades again or try a different island group, I settled on a compromise: it’s still the Cyclades, but this time it will be nearly all new islands that I’ve never visited before. Since I’m meeting Ed on Syros anyway, choosing a different group would have meant either a long ferry ride or internal flight to get to him. This way I’m close enough to meet up but still get to see new places.

My flight is scheduled to arrive in Athens on the 2nd of September, giving me a full two weeks to explore before I have to be on Syros. That gives me time for 3 or 4 islands with a mixture of 3 – 5 nights on each. Trying to avoid already visited islands narrowed things down a lot, with the western Cyclades islands being the obvious way to go.

Drafting an Itinerary

My first thought was to catch a ferry from Lavrio to Kea, then work downwards via Kythnos, Serifos, Sifnos and Milos. However, this puts me farther away from Syros at the end of the fortnight. I realised it would be better to start at the bottom (i.e. Milos) and work my way north instead. Thinking I had struck gold, I managed to find a late ferry from Piraeus to Milos that would avoid spending a night on the mainland. The ferry departs at 20:00, arriving on Milos at 00:45 the next day.

After some reflection, this actually didn’t feel ideal: I would still have to get from the airport to Piraeus, hang around for several hours, and wouldn’t arrive at my hotel until very late at night. If only there was another way of getting to Milos faster…

Oh yes, Milos has an airport!! Silly me. A quick check of the flight schedule and, sure enough, I can catch a 17:30 plane to Milos and be on the island by 18:15. Yes please and thank you very much!

Milos and Beyond

My parents visited Milos several years ago and really enjoyed it, so I was excited at the idea of visiting myself. It’s quite a big island, although most of the western side is uninhabited. I decided it would be worth staying 5 nights though, giving me plenty of time to explore as well as relaxing into the holiday spirit.

The next logical island to visit is Sifnos, just a short hop (40 minutes on a high-speed ferry) northeast. Truthfully, I don’t know much about this island yet – lots of research still to do – but I’ve pencilled in 3 nights which should be enough to at least take in the highlights.

Serifos, the next island in the group as you head north, is also a bit of a mystery to me. Apparently quieter than Sifnos, it’s currently a ‘maybe’ on my list, also for 3 nights. I probably will include it though, because the alternative is likely to be an island I’ve already visited (possibly Folegandros or Ios) and I really want to see new places for myself and get some more content for my website and YouTube channel.

Switching Tracks

At this point, I decided I will have to re-visit an island I’ve been to before: Paros. After experimenting with ferry routes, I couldn’t see an easy way of getting from Kythnos (the next island north from Serifos) to Syros, despite them being pretty close together. There are ferry connections, but not regular enough to make my itinerary work.

As I only spent two nights on Paros back in 2017 and was recovering from a bout of sunstroke at the time, I can’t really say I’ve seen much of the island yet anyway. This time, I’ll have three nights available and plan to stay in Naousa instead of Paros town.

From Paros, there’s an afternoon ferry to Syros that gets me on the island at 15:50 with enough time to catch a bus to one of the beaches on the south/west of the island. Syros apparently has a very good bus service as it’s quite an affluent island in spite of its relatively small size.

Ed was originally due to arrive late in the evening on the 16th, but since I began my planning, he’s had a slight change of plan and is spending his first night on Andros instead. He will then catch a ferry the next morning that gets him onto Syros around 10:00.

Revisiting Andros (and briefly, Tinos)

Ed and I will then have 24 hours to explore Syros. Not long, admittedly, but hopefully enough time to get a decent walk or two in and see a few sights along the way. Next morning, we’ll catch the 11:30 Blue Star ferry to Tinos with a two-hour stop-over on the way to Andros, our final destination for 3 nights.

We visited Andros back in 2017 and both loved the island, but only had two nights and arrived fairly late on the first day too, so really it was just one full day to explore. As it’s another large island, this time we’ll have two full days to find some new hiking paths and hopefully some beach bars too!

Finally, on Monday morning we plan to catch either the 10:15 or 12:30 ferry to Rafina for our afternoon flight home via Athens airport. The later ferry would give us a couple of extra hours to chill out in the morning, but with a risk of being late for our flight, if it doesn’t turn up on time and even if it does, we’ll probably have to pay for a taxi to get us to the airport quickly.

In total, I’ll be in Greece 19 nights: my longest trip so far (if only by two nights). Just need to keep my fingers crossed now that Covid restrictions don’t get worse before I’m due to fly out…