Sep 24, 2023 12 min read

Backpacking, Hop-on Hop-off Through the Cyclades, Greece

In this article, I will tell you about my most recent Greek experience (you know that Greece is our greatest weakness!), a different kind of experience, setting aside a few destinations which, I hope, to return to someday and write a bit more about.

Chora, Ios, Cyclades Islands, Greece
Chora, Ios
Table of Contents

For a long time, I had in mind a hop-on hop-off type trip, a kind of tour, seeing over time many tourists moving confidently between the Greek islands with nothing but a backpack.

I admired them both for the initiative to travel from island to island, and for managing to have minimalist luggage, something I believed at that time I could never do.

But, in the meantime, things have changed, and with each vacation that passed, I gained experience, helping us to reconsider our opinion about luggage.

A few years ago, I couldn't even imagine going somewhere without at least a small suitcase, but over time I realized that I could manage with less, especially when you have to lug around luggage, my husband anyway always limited himself to less luggage, being more organized and efficient from this point of view.

The Cycladic Islands, briefly the Cyclades, have always been a major attraction, and I admit that we fell in love with them some time ago, when we had the chance to visit a few of them.

From Skaros to Oia, Santorini
From Skaros to Oia, Santorini

When my husband came up with the idea of a circuit among the Cyclades with just a backpack, for me it was a big challenge which I thought I could face with some wisdom and prudence.

That is, to be able to give up luxury and to take with me only the bare essentials. Of course, with the possibility of buying anything necessary or desired from anywhere even if it would be more costly.

With this principle in mind, I accepted the challenge of going on a circuit-plus-stay vacation for ten days with limited luggage, but with all the essentials covered.

How We Organized The Vacation to Greece

We meticulously prepared everything after the idea of a different kind of vacation through the Cyclades became the main topic, essentially a ferry slalom among the smaller islands of the archipelago while also taking advantage of the direct flight to/from Santorini operated by Wizzair for the past three years, which has proven to be a real success, given it has maintained a frequency of three flights each week.

My husband gave me free rein to devise a feasible plan organized by days, including which islands we would visit or stay on, how long we would stay and where, which ferry routes to take, etc., all in detail.

After setting the vacation period between September 11-21, based on the flight days to/from Santorini, I let my neurons loose to think of a feasible schedule without it becoming exhausting.

The circuit was initially designed as follows: the first two days in Santorini, three days on the island of Ios, the next three days on the island of Folegandros, and the last two days back in Santorini to be ready for the return trip home.

Folegandros, a Jewel of an Island in Greece
I had heard about this little island in the southwest of the Cyclades Archipelago for a long time, and back then, I never imagined we would someday visit it.

We chose to allocate two days at the end instead of just one to avoid the risk of missing the plane in case there was any change with the ferry for whatever reason.

Of course, changes could also occur within the intermediate intervals due to various factors and indeed they did, so the final form would only be finalized after some time.

Immediately, I set out to look for accommodations, and my reliable friend did its job by offering me a wide range of accommodations, albeit quite pricey, even though these were early or very early bookings, more than ten months in advance.

After spending some time in front of the computer, sifting through everything that seemed to fit us, I decided to go for four accommodations: two in Santorini, one on the west coast at the beginning and another on the east coast at the end, one in Ios, and another in Folegandros.

The movement between the islands remained the tricky issue upon which the accommodations could be finalized in this form or not, except that the summer schedule of the more affordable ferries was to appear at the earliest in spring, with the exception of one, the Santorini-Ios route which was available from January 2023.

It was operated by a small company, aptly named Mikres Kyklades Lines, by skilled, bold, and fearless sailors with a tradition of several generations in navigation.

I immediately bought tickets for €22.4 (€8.70 per person + €5 fees) without hesitating too much since in 8-9 months a lot can happen, and the amount wasn't a fortune, so I wouldn't have major regrets.

Then, followed a long period of waiting, until the beginning of June when, a website specialized in ferry services, offered me options with tickets at more reasonable prices, maybe not as fast, but quite okay for us.

I quickly noticed that on the planned day for moving from Ios to Folegandros, there were no ferries running, so I extended the stay in Ios by one more night and, conversely, reduced the stay in Folegandros, which was possible with somewhat comparable costs.

I purchased the ferry tickets online; the chosen company was Zante Ferries, and the prices were modest: €5.5 per person for the Ios-Folegandros segment and €7 per person for the Ios-Santorini segment.

The idea was that even then, a completely unforeseen factor appeared, namely a strike by water transport workers following an unfortunate event at the beginning of September resulting in the death of a passenger who was denied boarding by the crew of a ferry and prevented from getting on it.

The strike was announced for September 16, and since our travel was scheduled for September 17, we believed we would not be affected. However, on the afternoon of September 15, we received an email informing us that due to the strike, our vessel's departure was changed in Ios, from 09:05 in the morning to 22:35 in the evening.

In such a situation, we had to notify our host in Folegandros that we would be arriving at midnight, and also ask our host in Ios to keep our luggage during the day, which we would spend wandering around Ios.

We were not pleased at all, but at that moment, that's how we thought to proceed, and we even managed to speak with both hosts.

The next day in the evening, at the eleventh hour, it occurred to me to check the same website to see what was available the following day to Folegandros and, to my astonishment, there was a departure at 10:30 in the morning to Folegandros by another vessel, a small one, just for passengers, named Maistros Santorini, with cheap tickets: €8 per person.

I immediately bought the tickets, happy that our stay in Folegandros was not affected. I notified our host there again, and everything ended well, the fact that we lost two cheap tickets was negligible compared to the satisfaction of being able to spend the planned time in Folegandros, which had already been shortened once.

The last ferry ride went smoothly, according to the scheduled timetable, with the departure from Folegandros at 16:30 and the arrival in Santorini at 19:20, witnessing another magnificent sunset in the Caldera from the ship.

I must say that transfers to/from the ports were provided for free by the hoteliers; I observed that these smaller islanders, less overwhelmed by congestion, are more hospitable in this regard.

Of course, things were different in Santorini, where the transfer from the airport to the first accommodation cost €20, the same as the transfer to the port, and the transfer from the port to the second accommodation, provided by them, cost €35. Expensive, but there's not much you can do!

These were the logistical details of the trip, admittedly not very simple, but when you enjoy organizing, nothing seems too complicated.

Daily Schedule of our Greece Trip

Days one and two were dedicated to the island of Santorini, the first was for settling in and pleasant reunions and reminiscences, especially since it was entirely at our disposal, landing in the morning at 08:00.

Oia, Santorini, seen from the boat, from the Caldera
Oia, Santorini, seen from the boat, from the Caldera

I had already spent a week in Santorini three years ago. We revisited the enchanting Caldera, which gives the island its uniqueness, having been "mutilated" by the volcanic eruption over 3,500 years ago. In the evening, we witnessed our first sunset, absolutely magnificent.

On the second day, since we had planned to redo the Fira-Oia hike, a ten-kilometer journey, to catch the famous sunset from Oia, we spent the first part of the day on a short bus trip to Kamari, one of the largest resorts on the east coast.

The path between Fira and Oia
The path between Fira and Oia

Three years ago, we had our accommodation in Perissa and didn't manage to visit Kamari, so we wanted to see what it was like. We stayed there for lunch at one of the taverns, then took the bus back to Fira.

Once we arrived at our accommodation in Firostefani, we geared up appropriately, took what we needed, with water being absolutely essential, and set off on our way as the hiking trail passed right by our accommodation.

Because I wrote an article dedicated to this experience, I will only mention that this time we deviated to the Skaros Rock in Imerovigli, where a few centuries ago the island's capital was located and one of the five castles built by the Venetians on Thira stood.

Skaros, Santorini, the rock we finally reached
Skaros, Santorini, the rock we finally reached

The fortress was definitively destroyed by the earthquake in 1956. The ruins are partially accessible, with a considerable degree of risk about which the hiker is warned through signs.

The path, in its entirety, is no longer in good condition, having degraded further, but remains passable.

We encountered a wedding at one of the luxurious resorts on our path, saw the bride and groom at their photo session in front of the church, taking it as a good sign, that it brings us luck.

The sunset from Oia is truly splendid, but it has become a big, overhyped deal, with the small town proving too small for the hordes of tourists who trample it, arriving specially by the dozens of coaches and creating an indescribable congestion.

The first sunset in Fira
The first sunset in Fira

There's literally no room to move, and you can't get anywhere near the Venetian castle, considered to be the best spot to admire the sunset. We barely managed to squeeze into one of the side streets where we had a not-so-great view, but we had to settle for less compared to last time.

On the third day, after breakfast, we packed our bags and left with our host for the port from where we were heading to Ios. After a journey of more than an hour on a sea rather choppy due to the Meltemi winds, but on a historic vessel, "Express Skopelitis", masterfully piloted by a crew of "old sea wolves", we arrived at the port in Ios.

Ios is a small island, famous for fun and beautiful beaches. Typically Cycladic, arid, with cube-like white houses, as if made of sugar, often swept by dry winds, Ios fits perfectly into the style of the archipelago but stands out through its vibrant nightlife and the presence of mostly young people, being known as the second Mykonos.

Of course, there are beautiful beaches, but also historical sites, with Ios known as the place where Homer went to die, having his tomb here, or where prehistoric ruins are found at Skarkos. The sunsets here are also events not to be missed.

Sunset in Chora Ios
Sunset in Chora Ios

In Ios, we had a rented car for three days (a Kia Picanto at €35/day facilitated by the host), during which we explored the island far and wide, enjoying a successful mix of visits to the island's attractions and relaxation at the beach or swimming, which I hope to discuss separately.

On the morning of the seventh day, after breakfast, we again gathered our bags, checked out, and went to the port to board the small vessel Maistros Santorini that was to transport us to Folegandros, and by noon, after just over an hour, we were disembarked at the port of Karavostasis.

Here we were awaited by the host's envoy and transferred to the property, in Chora, the capital of the tiny Folegandros.

About Chora of Folegandros, I can tell you it is magical, with a charm that's hard to describe. As traditional as it is with its specific Cycladic architecture, it is equally refined.

the narrow streets of Chora Folegandros
the narrow streets of Chora Folegandros

It exceeded all our expectations in every way, and we instantly fell in love with the little village-capital, so much so that in the two half-days and one full day we had at our disposal, we roamed its streets, gaping in awe here and there.

Of course, with breaks for sea and sun baths, not missing Agali Beach, one of the island's best. On the other hand, Folegandros truly deserves a separate article, which I will write.

We made sure to spend the two sunsets that caught us there, like many other tourists, at the Panagia church, the symbol of the island, perched on a rock several hundred meters above the sea, reached by a zigzagging white path, with the climb itself being a challenge.

Panagia Church
Panagia Church

On the ninth day, in the afternoon, we parted from charming Folegandros with difficulty, heading to the port from where our vessel "Dyonisios Solomos" of Zante Ferries was to pick us up and take us to the port of Athinios in Santorini.

The vessel is massive and offers a plethora of services and seating categories, but it has one big flaw, if you can call it that: it's slow, which suited us just fine.

From the ferry, we admired a new sunset, exactly as we entered the Caldera, so I can say we were incredibly lucky, as we encountered a multitude of small pleasure and excursion boats that bring tourists to the Caldera specifically to see the spectacle of the sun setting before going to bed, hiding behind the small island of Thirassia.

At the port, we were picked up and transferred to our last accommodation, located on the eastern coast of the island, in the area known as Exo Gialos where there is a port, a beach, and a few accommodation units.

Of course, there's also a beautiful church, Agios Nikolaos, because after all, Santorini is the island where you find more churches than houses, more donkeys than men, and more wine than water, as a local saying goes.

In the evening, we stayed in Fira until late at night, attending a show offered by the local organizers of a beer and wine festival named Volcano, where live Greek music, dancing, beer, and wine were the ingredients for successful entertainment.

On the last day in Santorini, the tenth, we had planned to spend the first part of the day at the beach, then in the capital, Fira, where we would stay again until late at night, having many things to do: to walk the streets hanging off the edge of the Caldera, to admire one last sunset which promised to be just as explosive in terms of colors, the sky being clear although Meltemi had started to blow annoyingly since the morning, and in the evening to go to the show again, since the festival was still in full swing.

Fira, the capital of the island of Santorini and the Caldera
Fira, the capital of the island of Santorini and the Caldera

The atmosphere was truly memorable, in tune with the entire vacation, indeed!

On the morning of the eleventh day, we had a flight at 08:30, abruptly transitioning from vacation mode to the everyday routine of home.

That's how this vacation, different from before, unfolded, a circuit outlined well in advance, with some modifications along the way, but materialized in a very good form.

Prices We Paid on This Greek Vacation

Contrary to many opinions that claim prices in the Cyclades, islands frequented especially by American, Italian, French, Canadian tourists, are high, I can honestly say they are not much higher than those on other Greek islands.

For example, a meal for two people with an appetizer, two main courses, half a liter of wine, water, was around 33-40 €, with the most expensive meal reaching 52 €.

In most places, we were offered dessert on the house, and the best food we had was in Folegandros, where the food was downright delicious, but also at a local tavern in Firostefani, with incredible dishes.

We paid with a card everywhere without any issues, but also with cash. Gasoline cost about 2.3 €/liter, and goods in small shops were similarly priced across all three islands, but slightly more expensive than on the mainland.


The southern Cyclades can be easily approached from Santorini, it only remains to "craft" a suitable program for each individual.

Of course, one must also account for the "unexpected," a sort of "surprise," which must be faced under any circumstances, but anyway, in every trip, there's a very small dose of it right from the start, from the moment you leave home, so caution is needed in all aspects.

This trip was a success, and I was very pleased that my effort to piece together many pieces of information obtained during many hours of research spent in front of the computer paid off, with the satisfaction being proportional.

It turns out it is possible to travel and manage with just a carry-on bag for ten days among the Greek islands, without feeling like you're missing anything. We thoroughly enjoyed the experience and believe we will repeat it similarly with other islands, which I also wish for you.

Thank you for reading and make sure to subscribe. We're constantly exploring new destinations and share our stories, tips, and the beauty we discover along the way.

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