Greece: Itinerary for a Solo Backpacking Trip in the Cyclades

To the point Here is my experience of a 2 week itinerary in the Cyclades (Greece) as a solo backpacker!

In 2016, I was living in England, where I had just spent 3 years working for a company located in Cambridge. I loved living in Europe (this was just before the Brexit vote, by the way…), because I could go on trips very often for very low prices!

If there was one destination on my list, it was Greece. I’ve been dreaming about it since I was a little girl!


There was a time when I knew everything about the Greek gods, and I wanted to visit Athens more than anything. As I grew up, I found the beaches and the beautiful landscapes of this country more and more attractive. But most of all… I knew that almost every restaurant there offers tzatziki. 🙂

I booked my flight from London Stansted to Athens, for the end of May, returning two weeks later. From Quebec, it is possible to book with Air Canada (and use Aeroplan points) from Montreal to Athens, which is a direct flight.

Also, don’t forget to have a credit card with no foreign currency conversion fees. You will save 2.5% on every transaction in Greece!

Greece Travel - When to go to Greece

Greece can be visited all year round, depending on the activities you would like to do. Obviously, it is a rather large country and there are all kinds of landscapes.

For my first visit, I wanted to see Athens and the Cyclades. I chose to go in May, since it’s just before the beginning of the tourist season and the weather is nice. The only problem is that the Mediterranean has not yet had time to warm up. For us who are used to the cold of the Atlantic, this is not really a problem!

Greece Travel - My Budget


Greece Travel - My itinerary

Athens (2 nights) – Mykonos (2 nights) – Naxos (3 nights) – Paros (3 nights) – Santorini (4 nights)

  • Flight between Athens and Mykonos : $25 with Ryanair
  • Ferry from Mykonos to Naxos: $40 (40 minutes)
  • Ferry between Naxos and Paros: $13 (45 minutes)
  • Ferry from Paros to Santorini: $30 (3 hours)

For example, you could use points from the American Express Cobalt® Card for all those travel purchases (plane tickets, boat tickets, etc).

To sleep, I alternated between youth hostels and cheap hotels.


Once at Athens International Airport Eleftherios-Venizelos, there are two ways to reach the city centre by public transport: by bus, or by metro.

I chose the metro (10 euros) on arrival, as it was quicker and I wanted to enjoy the afternoon there, as I only had two more full days to visit.

I took my backpack to the hostel and went out to explore. My first mission: to find tzatziki. The waiter must have thought I was a bit weird to order a plate of this fabulous dip when it wasn’t on the menu (!!!), but whatever! I was ecstatic.


I spent a few hours exploring the city, observing its inhabitants, smiling blissfully because I was happy to finally be there.

At 6:00 p.m., I had an appointment with a long-time friend I had met a few years earlier in Montreal. Dimitri is a native of Athens and was happy to show me a beautiful viewpoint unknown to tourists! We had a great evening at a comedy show (in Greek – I didn’t understand any of it, but the beer was good), then I went back to the hostel to sleep.


The next day, I took the opportunity to try two places recommended by a Greek friend: Kostas’ for the best gyro (pronounced “yiro” and not “jiro”) and Six d.o.g.s, an open-air pub known mostly to the locals. The result (a happy Maude!):

Bière au Six d.o.g.s

I went to burn off the ingested calories by visiting the Acropolis, which is a short walk from the city center. Another check mark on my life’s to-do list!


Back at the hostel, I met a Quebec woman who had just arrived. She told me that she had been offered tickets for a tour of Athens on the ” Hop on, Hop off ” bus and offered me to join her the next day.

I agreed; it would allow me to cover more territory, as I had only one day left before leaving for Mykonos.


To get to this island famous for its rows of windmills dating back to the 16th century, on a hill overlooking the town of Mykonos, and for its festive beaches, I had to go back to the airport (by bus this time – 3 euros instead of 10 for the metro; every saving counts!) Everything went well. The bus and metro infrastructure is well developed and safe in Athens.

In Mykonos, I had booked a small apartment a few meters from the beach of Ornos. I had planned to do some work there in the morning with my laptop, while sipping a good coffee on the balcony. I loved this little apartment so close to everything!

I was also able to try a few not-so-touristy restaurants, where I was offered mastiha liquor, a digestive that I really liked. It is a brandy-like liqueur made on the island of Chios, one of the few places in the world where the mastic tree is traditionally grown. You can find some at the SAQ (Skinos brand), if you want to try it!


I was able to visit the village of Mykonos and Little Venice, spending hours wandering through the beautiful little streets and admiring the contrasting colors. In the afternoon, I went to Paradise Beach, which turns into a huge party after 7pm. I’m not much of a party aninmal, so I stayed just long enough to get a little tan.

Mykonos Little Venice
Paradise Beach
Paradise Beach
Moulins de Mykonos


The island of Naxos, in the southern Aegean, is the largest of the Cyclades. Its fertile landscape covers mountain villages, ancient ruins and long beaches.


Its namesake capital (also called Hora or Chora) is a port city filled with whitewashed cube houses and medieval Venetian mansions.


I spent 3 days there lounging on the beach, reading and walking in the hills. Wine lovers could also take the opportunity to visit some vineyards, as the island is known for its good wines.

It is said that Dionysus lived here and that he gave the secret of the vine to its inhabitants…

I really liked this island, which has managed to preserve its identity and its wilderness despite the boom in tourism.



There were eight days left on my trip, which I had decided to divide equally between Paros and Santorini. I chose Paros a bit at randomm becayse of the logistics of transport to Santorini, and I do not regret ait t all.

This island is located west of Naxos in the Cyclades archipelago, of which it is the third largest island by area as well as the main maritime crossroads. I had booked a room in a beachfront hotel there and my only plans were to read in the sun, eat (tzatziki, you guessed it) and drink mastiha liquor.


On the second day of my stay, I stumbled upon a Canadian couple who had booked an outing on a private boat. They had one spot left – did I want to join them? Uh… yeah. So we set off to explore the Mediterranean, including a hearty meal. I took the opportunity to swim in turquoise waters… and I saw dolphins!

Dauphins Paros


Who hasn’t pictured themselves in Santorini? In any case, I’ve been dreaming about it for a very long time. It’s a romantic destination that you rarely visit alone, but I didn’t mind in the least. By the way, a word about travelling alone…

I find that solo travel allows you to open up to others, to discover facets of yourself that you had forgotten (or that you didn’t know yet), and above all, to do exactly what you want to do. I want to stay longer on the beach? I’m staying longer. I have a sudden craving for ice cream? I’ll get some. I want to watch people pass by for a while longer? No problem.


Let’s go back to Santorini. I arrived in the early afternoon. I had planned to spend 4 nights on the island, then fly to Athens on the last night, sleep in the airport (…never again) and fly back to Cambridge afterwards.

First of all, four days on this island is a bit long. It’s beautiful, yes. Even more beautiful than all those pictures you see everywhere! But there is not so much to do there, apart from lounging on the beaches and visiting the wonderful alleys of Thira and Oia (at least, that was my impression). I loved my stay! But if I had to do it again, I would spend two days there and not four.


I still had plenty of time to visit the black sandy beach of Perissa, walk around a lot, spend time at my hotel’s pool, and enjoy some amazing sunsets (the most beautiful after Vietnam!).


The last night was the day before my birthday. So I treated myself to a platter of cold cuts and a glass of Greek white wine, dry as can be, and watched the sun go down quietly over the Aegean Sea.


Then it was time to go back to Athens and spend one of the longest nights of my life, before my flight scheduled at 8am the next morning. Ah, what we wouldn’t do to save a few bucks…

Let’s just say that now that I’m a little more familiar with the strategies of points and rewards programs, I’d make sure to pay for a night in a hotel near the airport instead of trying to sleep IN the airport. Apparently it’s not allowed – the security guards had fun waking up all the poor tourists scattered around the terminal. In short. Did I learn my lesson ?

To fly to Greece with points, there are various options. On the Aeroplan side, direct flights between Montreal and Athens are subject to dynamic pricing as Air Canada operates them. It is best to look for availability with a partner airline; even if it involves a connection, you can save a lot of money. This is an important tip to remember to find the best prices with Aeroplan.

Greece Aeroplan

Then, compare it to the value of a comparable flight in cash to determine if it is better to use Aeroplan points to go to Greece or if travel rewards are preferable. Indeed, you can use Google Flights to find the best flight prices and then make your calculations.

Finally, check out the Flying Blue Promo Rewards! There are sometimes amazing deals to be seized! That’s why American Express Membership Rewards points are so valuable because they are transferable to various programs including Aeroplan and Flying Blue.

Greece Flying Blue

Greece Travel - Activities to book

Here are the activities we recommend you book with Viator:

Greece Travel - Accommodation

Book your accommodation in Greece with Booking (and read our article about all-inclusive in Greece):

Bottom line

I have only been able to see a small part of the beautiful country of Greece, and I am already looking forward to going back.

My next stay will be devoted to visit Meteora, on the continental side of the country. Do you know it? Feel free to send me your comments or recommendations on the facebook group, if any!

Come to discuss that topic in our Facebook Group!
4.3 Milesopedia Rating
With her head full of exotic landscapes and food, Maude dreams of adding more destinations to her list of countries visited. Her survival kit: a good backpack, a Stephen King novel and a laptop.

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