9 Days in the Cyclades, Greece – Milos, Naxos and Mykonos Itinerary

9 Days in the Cyclades, Greece – Milos, Naxos and Mykonos Itinerary

After a year of living in London, we learned that a sun-filled beach trip (or two) is necessary to surviving grey London summers (and winters… and autumns… and springs…). With time to take a longer trip at the end of September, Greece and the Cyclades seemed the perfect destination for a sun-seeking adventure. With over a week to play with, we spent time devising a 9 day itinerary exploring the Cyclades across Milos, Naxos and Mykonos.

Our trip began on Milos, then we traveled onto Naxos and then Mykonos via ferry. From Mykonos we were able to fly direct back to London on EasyJet. I’ll dig into each part of our trip in separate posts, but since it was a longer trip, I wanted to share our itinerary and our thoughts around planning our 9 day trip to the Cyclades in Greece.

After researching the many, many islands in the Cyclades, we decided that we wanted to visit Milos the most and that we wanted to fly directly back to London from the islands. With those two ideas set, we starting looking at ferry routes to pick a third stop along the way and decided on Naxos.

There were two options for flying directly back to London from the Cyclades: Santorini and Mykonos. At the advice of expat friends who had visited Santorini and a quick look at hotel pricing, we decided to omit that stop from our itinerary. We did see it from the ferry and it is beautiful. It is unique to the islands we visited as it is set up on a cliff overlooking the ocean, but we were looking for a more laid back trip. We compromised on two nights and one day in Mykonos in order to get back to London. After visiting Mykonos, we felt we made the right choice prioritizing spending time on the lesser known islands.

I should add that our original itinerary ended up changing due to a huge windstorm that swept through the Cyclades during our stay. From what we gathered, this is not that typical for late September, and something that happens more often in the winter. That said, I had read that the winds in the islands are something to consider and contend with if you are traveling between multiple islands. I’ll write about this in more detail as it was quite an experience that did have quite an impact on our trip.

Day 1 – Travel Day from London to Pollonia, Milos, Greece

Our trip started early on a Saturday morning in late September, when we took the 6:55am British Airways flight from London to Athens. There are two ways to get to Milos from Athens, either by ferry or by air on small, regional airlines. We opted to fly, saving ourselves hours of travel time.

Because our flight from Athens to Milos was on a different airline than our first flight, we passed through passport control in Athens and out into the general airport to check-in and check our bags for our next flight. We then re-entered through security to get to our gate.

From what we had read and then observed at the airport, delays on flights to islands are common. With small planes, small airports and winds to contend with, we weren’t all that surprised. The flight is super quick and takes you up over other islands which was really cool to see. My top pro-tip is to not buy sunscreen at the airport. Very expensive.

The airport on Milos is the smallest I’ve ever been to (and I’ve flown into the “international” airport in Watertown, NY). Though it is small, our bags arrived pretty quickly and we were able to rent a car from the airport with drop-off at ferry terminal. Our car was ready and waiting and we were quickly off to our home base on Milos, Pollonia.

Adamantas is Milos’ port city and therefore is the island’s busiest town. It’s not very picturesque, so we decided to stay in Pollonia. Though small, the harbor at Pollonia has everything a visitor could need – many restaurants, beaches and beautiful views all right there. We were very happy with our choice and our fantastic hotel, Villa Tania.

Day 2 – Milos – Sarakíniko, Mandrakia and Plaka

To really make the most of a stay on Milos, renting a car is a must. On our first full day on the island, the weather was sunny and warm, so we drove to the gorgeous beaches of Sarakíniko.

After a few hours exploring, swimming and sunbathing, we drove over to Mandrakia for lunch at Medousa. It was gorgeous and our lunch was delicious.

Later that afternoon we headed over to Plaka to see some sights, including the catacombs and the amphitheater were the Venus de Milo was discovered, and to watch the sunset. Set high on a hill, the sunset views are amazing.

Day 3 – Milos – Day Tour to Kleftiko

We knew that our sailing tour to Kleftiko would likely be the highlight of our trip to the Cyclades and we were not disappointed. We set sail with Polco Sailing from Adamantas to these beautiful caves with many gorgeous stops along the way. It was a blissful day and a great way to enjoy the calm before the storm…

Day 4 – Milos to Naxos via Ferry

We originally planned to spend our fourth day on Milos exploring more of its natural wonders and hopefully having another beach day. However, with a windstorm approaching, we were lucky enough to get tickets on an earlier ferry to Naxos. The ferry takes several hours, stopping at many other islands, including Santorini, along the way.

In short, it was pretty chaotic as we battled the crowds eager to outrun the storm that filled each seat on our ferry. There was a point where we found out via overhearing shouting from the lower deck of the ferry that anyone headed to Naxos was meant to get off the ferry right then at Santorini and switch to another. We had to quickly push through the crowd down the stairs with our bags, where once we reached the bottom, we were almost pulled off the ship by staff.

Once outside, we found ourselves herded to start running across the docks to another, much larger ferry that was headed straight to Naxos from there. The ferry staff shouted and ran alongside us as we dashed to make the boat. It was so ridiculous we could only laugh and I wish I had had my phone handy to video the whole thing. It was bananas!

We were super lucky to have made that ferry. The much larger, faster and nicer ferry took us directly to Naxos and shaved an hour or two off our travel time for the day. The larger ferry also handled the waves from the storm much better!

Approaching Naxos was incredible. We were greeted by the sight of the beautiful port city set on a hill with the ancient Portera facing out to the ocean. It is truly a remarkable sight.

We stayed just outside the port at Hotel Galaxy. Though it did not have the character of Tania, it was nice and the location was perfect. It would have been amazing had we had the weather we were expecting.

Day 5 – Naxos – Kouros, Chalkio, Apeiranthos and the Temple of Demeter

The storm really set in this day. Our vision of a day that took us from the pool to the beach and back, filled with bike rides to different beaches, swimming and a fruity cocktail or few at the rustic beach bars quickly became a bit of a joke. A combination of clouds, falling temperatures and strong winds that closed the beaches pushed us toward new plans.

Moving quickly, we rented a car to explore the many fascinating and ancient sights of Naxos. In just a few hours, we were able to explore much of the island along its winding, hilly roads including Kouros, Chalkio, Apeiranthos and the Temple of Demeter. Not bad for a spur of the moment itinerary!

That afternoon we explored Naxos town and that evening we found delicious cocktails before dinner at the rustic Lucullus.

Day 6 – Naxos

Though the clouds and cold weather persisted, we did our best to stick to our original plans this day, reading by the pool, going for a run, trying a beach bar and dining on the beach. It was cold but relaxing!

Shelter from the rain, cheap Greek wine and playing cards… how to enjoy a windstorm on Naxos!

Day 7 – Naxos to Mykonos

After a couple cold days on Naxos, we lined up for another chaotic ferry journey, this time to Mykonos. We had secured tickets for the first operating ferry to Naxos after the storm, along with many people who had flights out of Mykonos just hours later. Our ferry was delayed and those poor souls waited as the likelihood of making their flights grew smaller and smaller.

When the ferry finally arrived, we boarded no problem. Getting off the ferry was a different story. With limited taxis on the island of Mykonos, it was a mad rush off the ferry in which I fell and scraped up my knee. Andrew had found us some sort of rickshaw situation to get to our resort and as we sped along, clinging to the sides of it for dear life, I was feeling very ready to go home. Like joking we should move our flights. Or make a friend with a hot tub so we could at least say wore our bathing suits on a 1/3 of our beach trip.

Just when I hit my travel rock bottom, our luck changed. We had used points to book the nicest hotel of our trip (and all of 2018) on Mykonos. When we got to our room we discovered we had been upgraded. We had our own hot tub looking out over the ocean! And then the sun came out! It was true bliss. Vacation saved. Best day ever.

Day 8 – Mykonos

Though the weather was still iffy, we rented an ATV and checked out two beaches in the morning, Psarou and Platis Gialos. We enjoyed our upgrade, then headed into Mykonos town to explore more in the evening.

Day 9 – Travel to London from Mykonos

Remarkably, this was probably the unluckiest we’ve been on any trip during our expat experience. I say remarkable because, overall, it was a fantastic trip to beautiful and interesting places. It didn’t go quite to plan, but we certainly did our best to make the most of it and our room upgrade surprise at the end went a long way in making up for the less-than-perfect weather.

On our last day, it was pouring rain as we set off to the airport in Mykonos. It was packed and flights were delayed due to the rain, but we made it out close to on time and fortunately were able to make sense of the crowded chaos to board and head off on our way. By that point, the crappy weather and chaotic delays felt almost a fitting end to this trip.

I hope this itinerary doesn’t come off as too negative, because I’d do this trip over again in a heartbeat! Windstorms, crazy ferries and all. Milos and Naxos are such special places and we had a great time exploring the parts of Mykonos we had time to see. Our original itinerary of one more day on Milos and one less day on Naxos would have been perfect, but our trip was fabulous just the way it was. If you are planning a trip to the beautiful Cyclades in Greece, I am envious and I hope you have a wonderful time!


Jenn is an American expat living in London, spending her time freelancing, traveling and writing on this here blog. Thank you for reading. Are you planning a trip here? Tell me your plans in the comments!

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