Last updated on November 20th, 2022
Unexpected adventures in Crete, Ios, Naxos and Santorini
by Carolyn Ray, Editor, JourneyWoman
Imagine this: you’ve just travelled halfway around the world for a week-long beach holiday in Crete, one of the most beautiful places in the world. You pull into your dream homestay, confident in your ability to choose the most perfect place… only to discover it’s in an industrial parking lot, surrounded by piles of gravel, and nowhere near the town or the beach you had imagined spending your days on.
That’s what happened to me in Chania, Crete. And as a result, I had no choice but to throw my meticulously planned travel itinerary out the window, wish it well, and let the universe guide me. What I learned has influenced the way I travel forever. Goodbye schedule, hello freedom!
After months of planning, I had created a detailed itinerary that included stops in Crete, Santorini, Naxos and Rhodes, and Athens. Since it was my first time, I wanted to have a range of fulfilling and dreamlike experiences, including Airbnbs, cave houses and boutique hotels.
Ferries, planes, car rental – check.
Tickets purchased, routes laid out, and all boarding times itemized. Check.
At least, that was ‘the plan’.
Arriving in Chania, Crete
We arrived in Crete at midnight after almost 24 hours of travel, from Toronto to Athens to Heraklion. My daughter Alyx, her friend Rebecca, and I piled into a taxi and headed for Chania. The driver, a local, wasn’t able to find the address. Not a good start.
When we finally located it, things were not what I expected. My lovely Airbnb ‘elegant Cretan mansion’ was simply not going to cut it.

While it looked close to the beach on a map, it was actually located at least 20 minutes away in an industrial area, surrounded by a gravel pit and guarded by the most enormous and ferocious Rottweiler I had ever seen, straining at his leash. This didn’t feel safe, nor did it feel like what had been advertised.
We had no choice but to stay the first night due to jet lag, but the next morning I awoke early, found a car rental agency and told the Airbnb owner we were hitting the open road.

Crete’s terrain is mountainous / Photo from Envato Elenents
Falasarna
An hour later, bundled in a ratchedy Jimmy all-terrain vehicle, I drove east, toward Kissismous and followed a winding road that took us far up into the mountains. I had no map, no idea where I was heading, but I knew we would hit water at some point – this is an island, after all!
After about 90 minutes, olive groves appeared, and then, in the distance, I spotted the ocean, colourful umbrellas and a white sand beach. I had no idea where I was, but soon discovered that the beach in front of us was Falasarna. Not only is it one of the most famous beaches in Crete, it is also ranked as one of the top 10 beaches in Europe. The girls were beside themselves and began ripping bikinis out of their bags, ready to launch themselves into the turquoise water. However, I had to find a place to stay, too.
The road narrowed and became a one-lane dirt road. It ended in a surprising way: at Sunset Villas, a family-owned boutique hotel with a beautiful view and outside terrace covered in vines and flowers. Within 10 minutes, Maria had given us two perfect rooms, overlooking the beach, for about 50 euros. This was heaven!
Falasarma was the perfect place for us to feel the wind in my face and celebrate freedom. Turquoise water, fine sand, and a choice of beaches – some with rocky shores and other, more intimate beaches. I spent the day in the water, jet skiing, reading, and enjoying the warm sunshine. I finally felt like I was on vacation. That night, we enjoyed a delicious homemade Greek dinner, serenaded by noisy and welcoming cicadas, at the taverna. It’s a moment I will never forget.

Family-owned Sunset Villas in Falasarma/ Photo provided by Carolyn Ray

Elanfonissi: One of the Top Beaches in the World
A few days later, I drove up into the mountains and followed the signs to Elafonissi, Greece’s top beach. A protected nature reserve, Elafonissi is simply surreal, with pink sand, giant coral above the water and clear, shallow waters. It was quite windy, but somehow that didn’t detract from the experience, with its shallow lagoon and island. It felt like I was in the South Seas.
After spending the day there, it was time to find a place to sleep. With my two expert navigators leading the way, I drove an hour south to Paleochora, which is incredibly quaint, with open-air restaurants, musicians and a beachy kind of vibe. It’s also a stop for cruise ships, so was quite busy.
Quite by chance, while browsing in a store, I met the receptionist from the Hotel Glaros. She immediately secured a room for us for the night, in a town that was completely sold out.

The world famous Elafonissi Beach / Photo by Carolyn Ray
Santorini: Life in Cave House
Not my usual kind of place, but a lovely beach nonetheless and close to the ferry to Santorini, the next stop on our itinerary. I was surprised and impressed by the quality of the ferries: they are well run, generally on time and the interiors are just like an airplane, with assigned seating.
I was thrilled with our cave house, Casa Sigala, which I found on booking.com. It seemed suspended over the ocean, overlooking the caldera. The food in Santorini was outstanding: my favourites included poka, with its stunning views of the sunset. Both Lotza and Strogili had beautiful views of the caldera and boats zipping by far beneath us.
Eager to get on the water, we spent the first morning on a catamaran and toured nearby islands, including the volcano hot springs. It’s easy to see how this is considered to be the lost city of Atlantis; it’s so stunning. Sunsets and romance are in the in the air in Santorini, and I wish I could stayed longer. Alyx and Rebecca loved the shopping and the views; I think Snapchat had a busy day.


Naxos
The next island was on my list was Naxos, known for its stunning beaches, including Plaka and Agia Ana. Naxos appealed for its laid-back style, quaint old town and busy port in Naxos Town. With its churches, monasteries and Venetian castles, it’s very lush, scenic and fairly undiscovered. It’s famous for the Portara or Great Door, which sits on a small island that you can walk up to. Built in 530 BC, myth has it that this is where Ariadne, the Minoan princess, was abandoned by her lover, Theseus, after he killed Minotaur on the island of Crete.
On my first night in Naxos, we stayed at the boutique hotel Lagos Mare on Agios Prokopios beach. As I swam in the warm ocean, I decided to make another schedule change – to abandon the return trip to Athens via Rhodes. To get to Rhodes, I would have had to return to Santorini and take a 3 am ferry. This meant an entire day of travel. Being on a beach was definitely more appealing. I took a bus into Naxos Town, and cancelled my hotel in Rhodes, ferry and plane tickets.

Ios was calling!
Instead, I decided to visit a nearby island called Ios. I found a small, family-owned hotel called Psili Ammos, right on Mylopalatas Beach. This was a highlight of my trip, because of the family that owns this hotel and the Drakos Tavern underneath. Built over 60 years ago, this was the first hotel on the beach, which is now a top destination.
George gave us a lovely white stuccoed room room with blue shutters that overlooked the ocean, and his cousin served us dinner at the family taverna downstairs, where I ate octopus, fish and mussels caught that day in the ocean. On my last day, I took a bus to Maganari beach, a charming bay on the south side of Ios. It was so clear that I could see Santorini from my beach chairs. The return to Athens was on a fast-speed ferry, another change in my agenda, much more enjoyable than flying.

Just go with it!
My trip was unexpectedly spontaneous, full of rich and authentic experiences. Being able to live in the moment, follow the waves, and change direction like the breeze, made it even more exhilarating and memorable. I have a feeling the universe was sending me a clear message: just go with it. It’s a lesson I will remember.
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Thoroughly enjoyed your article Carolyn, free-wheeling around the Greek Islands would be my kind of holiday, love the feeling of the islands having been to corfu too, have noted your beaches & accoms for future planning!