I’ve lost track of how many Greek Islands I’ve been to this year – maybe 25 or 30. Earlier this year my husband, Simon, daughter, Sienna (age 4) and I sailed around the Ionian Islands, through the Corinth Canal to Athens and then all around the Aegean Sea on our 56’ sailboat.
Sailing through Greece over the summer was a dream come true
In the Aegean we hit the Sporades, Northeast Aegean, Cyclades, Dodecanese, Crete and Argo-Saronic Islands. We were also fortunate to visit several places along the Peloponnese and mainland Greece.
That being said, the most beautiful Greek destination I laid eye’s on was Santorini
Unfortunately, however, anchoring or finding a mooring in Santorini is near impossible. If you have a skipper or crew able to take command of your boat, you can take a dinghy to the small fishing port below the town.
There are four large mooring pillars outside the fishing port, as noted in the pilot book, however they’re for very large vessels. You have to tie yourself to the pillar and then run a very, very long line to the shore ensuring that you don’t spin. More than one vessel can use the mooring pillars and it’s not advised that you leave the vessel once tied on.
Our 56’ sailboat was too small to even consider tying onto the mooring pillar
On a few occasions Simon and I discussed sailing to Santorini in the hopes that we’d be able to find a place to anchor. One day we actually set sail for the island but diverted to Crete due to more favorable winds and the guarantee of a place to stay for the night!
Once we were in Crete I thought all hope was lost
I was never going to visit the famous Greek island of Santorini. I thought, ‘oh well – perhaps next year!’
As fate would have it, a friend of ours, Admiral Stefano (shown below), flew into Crete to join us for a while. We started to discuss our passage back towards Italy and I just happened to mention that I was disappointed to miss Santorini.
And that’s when Stefano said, ‘let’s go to Santorini and then we’ll make our way west towards the Peloponnese and then over to Italy. The winds are perfect for us to go North and then West.’
The smile on my face was massive
We set sail from Crete in the afternoon estimating that we’d arrive in Santorini the following day. Fortunately, Stefano and Simon took the night shift and Sienna and I slept most of the way to our destination.
When I awoke we were on the South side of Santorini heading to the North side to find a place to drop us off. Stefano offered to drive the boat around for a few hours while Sim, Sienna and I explored the town. Stefano made a visit to the island several years ago so he was happy to let us experience the island for ourselves.
We lowered our dinghy, motored over the extremely small fishing port and climbed up onto land
A big sign said, ‘Donkeys,’ so we followed the signs. Above us was a massive cliff with a winding path to the top.
When we arrived at the donkey station there were a bunch of old Greek men that looked as if they’ve lived outdoors their entire lives. We motioned to the donkeys and it didn’t take long for all three of us to be sitting on one. Simon took Sienna and I had a donkey all to myself.
I assumed that someone would lead the donkey up the hill but we were left to our own devices!
There wasn’t even a rein. You just sat on the donkey and hoped it went forward. We made it a few steps around the first turn and Simon’s donkey stopped. We both tried to lightly kick the donkey, like you do with a horse, but nothing worked.
After a few minutes some other people with donkeys came up behind us and ours started to move again.
A snail could have climbed the hill faster than we did!
That being said, it was the best 5 euros we’ve ever spent. Trying to get the donkeys to go forward and then ‘racing’ others was hysterical. I had a smile the entire time. And the view…Oh-my-gosh…the view as we climbed the hill was breathtaking.
We could see the gorgeous blue sea, the crater of the volcano, cruise ships, and loads of sailboats. I was in heaven.
Once at the top, I felt the pressure to see everything quickly as we only had a few hours
I also felt tired, hungry and thirsty. None of us slept very well – I never sleep good when we sail overnight. And I needed a hit of caffeine.
We stopped at the first restaurant overlooking the sea and ordered a few crepes and coffees. My eye’s were smiling just as much as my stomach was. The views were out of this world. I kept thinking, ‘I’m so freaking grateful to have had the opportunity to see such lovely sights.’
We then walked around looking at the shops, exploring the views from different vantage points and soaking up the atmosphere.
Santorini is such a remarkable place
Yes, it’s massively touristy
Yes, it’s expensive – our 3 crepes 2 coffees and a juice cost 40 euros. And yes, it’s full of foreigners. HOWEVER, it’s like no other Greek island. It’s like no other place that I’ve ever been to. Santorini truly is a special place.
While enjoying our meal we watched our boat motoring around the central volcanic crater
My husband and I reflected back to where we were the same time last year. If someone told us that we’d be in Santorini while a retired Admiral circled around waiting for us in our own 56’ Oyster yacht, we would have said, ‘no freaking way!’
This time last year we hadn’t yet sold our house and possessions nor had we purchased our around-the-world-sailing vessel.
In fact, we had no idea that we’d be signing up to such an adventure
Anyway, after walking around and seeing all that we could see, we found a bakery so to get Stefano bread. He’s Italian and feels out of place if there isn’t at least one loaf of bread laying around!
We grabbed some lovely fresh bread and then took the gondola from the top of the cliff to the bottom
The ride down was just as exciting as the donkey ride up however much quicker.
Our whirlwind viewing of Santorini was for 4 hours only but it was an exceptional four hours
My family and I are so grateful that Stefano motored the boat around while we took in the sights. And I’m over the moon that I was able to see the most spectacular Greek island ever.
Do I recommend that you visit Santorini – YES!
As a side note, Simon and I sailed to Crete with the intention of taking a ferry to Santorini. We assumed it wouldn’t cost much as the islands aren’t that far away. To our surprise, for a day trip it cost over 120 euros each person and that included four hours on a ferry. Knowing we could sail there for free caused us to decline the day trip option.
There might be other islands with secure anchorages that have a ferry service to Santorini – perhaps Kos? If you want to see the island, make sure to plan ahead as it is definitely worth sorting something out.