Greece: itinerary for a solo trip to the Cyclades

Updated Aug 14, 2026
Fact checked by
Marie-Ève Leclerc
Marie-Ève Leclerc Marie-Ève Leclerc
Marie-Ève, Web Director at Milesopedia, is an expert in budget travel and a slow travel enthusiast. Specializing in Aeroplan, Scene+, and Marriott Bonvoy programs, she spends nearly six months a year abroad, making travel her way of life. Constantly seeking the best waves to surf, excellent coffee, and strategies to extend her travels, she is often found in coworking spaces with fellow digital nomads or by the sea, watching the sunset.
All posts by Marie-Ève Leclerc
Greece: itinerary for a solo trip to the Cyclades
To the point From Santorini to Paros, via Mykonos, I share with you my experience of two weeks in the Cyclades, Greece.

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

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

Greece: Solo Travel Itinerary in the Cyclades - Santorini

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 above all, I knew that almost every restaurant there offers tzatziki. 🙂

So I booked my plane ticket from London Stansted to Athens, for a two-week vacation.

Greece – When to go?

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, as it’s just before the start of the tourist season and the weather is pleasant. The only snag is that the Mediterranean hasn’t had time to warm up yet. For those of us used to the cold of the Atlantic, it’s not really a problem!

Greece Travel – My Budget

I spent a few months quietly preparing my solo trip. As I wanted to enjoy my trip and do as many activities as possible, I made a budget.

Greece can quickly become expensive if you don’t book accommodation in advance. I wanted to change hotels one night, once I got there, and the prices had doubled.

I’d suggest having a general idea of the destinations you want to visit and planning a night without a reservation every now and then, in case you change your mind.

Smaller hotels are more likely to honor the price you paid if you want to change the date of stay a bit (at least in my experience).

If you want to go island-hopping, you should take the time to look at the different ferries. There are several companies offering services between the Cyclades islands.

I used the ferries.gr website to do my research. If you’re traveling in high season, I’d recommend booking the routes you consider important in advance. It’s not uncommon for boats to be fully booked for the most popular itineraries.

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

  • Flight between Athens and Mykonos, with Ryanair ;
  • Ferry between Mykonos and Naxos, 40 minutes;
  • Ferry between Naxos and Paros, 45 minutes;
  • Ferry between Paros and Santorini, three hours.

For sleeping, I alternated between youth hostels and inexpensive hotels.

Athens

Once at Athens International Airport Eleftherios Venizelos, you can reach the city center in two ways by public transport: by bus or by metro.

I chose the metro on arrival, as it was faster. And I wanted to make the most of the afternoon there, having only two other full days to visit.

I dropped my backpack off at the hostel and went back out to explore. My first mission: find some tzatziki. The waiter must have thought I was a bit strange ordering a plate of this fabulous dip when it wasn’t on the menu, but no matter! I was over the moon.

Greece: itinerary for a solo trip to the Cyclades - Tzatziki

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

At 6:00 PM, I had a meeting with a long-time friend I’d met a few years earlier in Montreal. Dimitri is a native of Athens and was delighted to show me a magnificent viewpoint unknown to tourists!

We had a great evening at a comedy show (in Greek—I didn’t understand a thing, but the beer was good), then I went back to sleep at the hostel.

Greece: itinerary for a solo trip to the Cyclades - Athens

The next day, I took the opportunity to try out 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 mainly to locals. The result: one happy Maude!

Greece: itinerary for a solo trip to the Cyclades - Kostas Gyro
Greece: itinerary for a solo trip to the Cyclades - Beer at Six d.o.g.s

I went to burn off the calories I’d consumed by visiting the Acropolis, which is within walking distance of the city center. Another tick on my bucket list!

Immerse yourself in ancient Greece with a visit to the Acropolis and Parthenon in Athens.

Greece: itinerary for a solo trip to the Cyclades - Archaeology

Back at the hostel, I met a Quebecer who had just arrived. She told me she’d been offered tickets for a bus tour of Athens and asked 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.

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 return to the airport: 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 out a few non-touristy restaurants, where I was offered mastiha liqueur, a digestif I really enjoyed. It’s a brandy-type liqueur, made on the island of Chios, one of the few places in the world where the mastic tree is traditionally grown.

Greece: itinerary for a solo trip to the Cyclades - Balcony

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.

Greece: itinerary for a solo trip to the Cyclades - Mykonos Little Venice
Greece: itinerary for a solo trip to the Cyclades - Paradise Beach
Greece: itinerary for a solo trip to the Cyclades - Mykonos
Greece: itinerary for a solo trip to the Cyclades - Mykonos Windmills

Naxos

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

Greece: itinerary for a solo trip to the Cyclades - Naxos

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

Greece: itinerary for a solo trip to the Cyclades - Naxos

I spent three 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 gave the secret of the vine to its inhabitants.

I really liked this island, which has managed to retain its identity and wild nature despite the boom in tourism.

Greece: itinerary for a solo trip to the Cyclades - Naxos

Paros

There were eight days left of my trip, which I’d decided to divide equally between Paros and Santorini. I chose Paros somewhat at random, dictated by the logistics of transport to Santorini, and I don’t regret that choice at all!

This island lies to the west of Naxos in the Cyclades archipelago, of which it is the third largest island by area and the main maritime hub. I’d booked a room in a beachfront hotel and my only plans were to read in the sun, eat (tzatziki, you guessed it) and drink mastiha liqueur.

Greece: itinerary for a solo trip to the Cyclades - Paros

On the second day of my stay, I happened upon a Canadian couple who had booked a trip on a private boat. They had one seat left—did I want to join them? Uh, yes. So off we went exploring the Mediterranean, including a hearty typical meal. I took the opportunity to swim in turquoise waters and saw dolphins!

Greece: itinerary for a solo trip to the Cyclades - Paros
Greece: itinerary for a solo trip to the Cyclades - Paros Dolphins

Santorini

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 traveling alone.

I find that solo travel allows you to open up to others, to discover facets of yourself you’d forgotten (or didn’t know yet), and above all, to do exactly what you feel like doing. Want to stay longer on the beach? I’ll stay longer. Got a sudden craving for ice cream? I’ll go get some. Want to watch the people go by for a bit longer? No problem.

Greece: Solo Travel Itinerary in the Cyclades - Santorini
Greece: Solo Travel Itinerary in the Cyclades - Santorini

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

Firstly, four days on this island is a bit long. It’s beautiful, yes. Even more beautiful than all those photos you see everywhere! But there isn’t that much to do there, other than lounging on the beaches and visiting the wonderful narrow streets of Thira and Oia (at least, that was my impression). I loved my stay! But if I had to do it again, I’d spend two days there instead of four.

Greece: Solo Travel Itinerary in the Cyclades - Santorini
Greece: Solo Travel Itinerary in the Cyclades - Santorini

I still kept busy: I visited the black sand beach of Perissa, walked extensively, and spent time at my hotel pool. I admired breathtaking sunsets (the most beautiful, after those in Vietnam!).

Greece: itinerary for a solo trip to the Cyclades - Sunset over Santorini

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.

Greece: Solo Travel Itinerary in the Cyclades - Santorini

Then it was time to return to Athens and spend one of the longest nights of my life, before my flight at eight the next morning. Ah, what we wouldn’t do to save a few pennies.

Let’s just say that now that I’m a bit more familiar with points and rewards program strategies, 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 forbidden: the security guards had fun waking up all the poor tourists scattered around the terminal. Anyway. I’ve learned my lesson!

Activities to book

Here are some of our suggestions:

Athens:

On the islands :

Greece – All inclusive

This formula generally offers good value for money. Here are our top suggestions for an all-inclusive trip to Greece.

In this article, you’ll see that it’s possible to considerably reduce the cost of an all-inclusive trip, thanks to reward points.

Save with points

On the flight

Air Canada’s Aeroplan loyalty program offers many benefits. In Canada, major banks offer Aeroplan co-branded credit cards, allowing you to earn points on your everyday spending.

In economy class, for a one-way flight from Montreal, you’ll need at least 40,000 points to reach Athens airport, according to the Air Canada points predictor.

Would you like to find out more about this loyalty program? Here is our Aeroplan beginner’s guide .

On accommodation

There are many Marriott Bonvoy hotels in Greece, including the Mystique, a Luxury Collection Hotel, Santorini and the Athens Marriott Hotel.

The Marriott Bonvoy loyalty program notably allows you to stay five nights for the price of four when booking a room with reward points.

There are several ways to earn Marriott Bonvoy points. The easiest way is via credit card. American Express offers two credit cards linked to this loyalty program:

Each of these cards allows you to earn Marriott Bonvoy points directly through your daily spending, but also through welcome offers.

You can also save on a charming Airbnb rental with travel points. All credit card issuers have programs with travel points.

Among the best programs in Canada, a few stand out:

Finally, regarding booking an independent hotel, there are also several tips for reducing costs, notably via online rewards portals.

On Foreign Currency Transactions

If you’re planning a trip to Greece, choose a credit card with no conversion fees. That’s 2.5% savings per transaction!

Discover our tips in our guide to saving on foreign currency transactions

Bottom Line

I’ve only been able to see a tiny part of this magnificent country, and I can’t wait to go back. Crete is also well worth a visit.

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!

Greece: itinerary for a solo trip to the Cyclades - Meteora

Frequently Asked Questions

Come to discuss that topic in our Facebook Group!
Maude Mainguy
Maude Mainguy
With her mind filled with exotic landscapes and dishes, Maude dreams of adding more destinations to her travel list. A travel agent specializing in small group and adventure travel, and an enthusiast of Aeroplan and Marriott Bonvoy programs, she shares tips for authentic and immersive experiences. Her survival kit includes a sturdy backpack, a Stephen King novel, and her laptop, ready to explore the world while staying connected.
All posts by Maude Mainguy
Region
Greece

Receive our newsletter every week!

Savings are this way:

Milesopedia