Following the Wind to Beautiful Places

One of the most incredible aspects of sailing is that you follow the wind where it takes you at whatever speed it takes you there. However, during a sailing charter there are certain places you need to be at certain times (I know, a little counterintuitive to the concept of sailing). 

Greece is known for Its strong winds and unpredictable swell, but luckily, it’s also known for Its vast array of stunning islands. Our skippered sailing charter is based in the Cyclades, and we start and end most of our trips within those islands. For example, we could begin in Syros (the home base of our boat), Mykonos, Paros, or another neighbouring island; and then finish a charter a week or so later somewhere in the Cyclades. The wind is almost always in our favour for this sort of trip. 

However, for one charter last summer this wasn’t the case. 

At the very beginning of August, 2018, we had a group of ten people sailing with us for ten days, embarking in Syros and also disembarking in Syros. Like before every charter, our skipper, Patrik, checked the weather predictions and attempted to plan a trip according to the wind, start and end destinations, client requests, and the length of the charter. This time the predictions were alarming. As far as we knew, the winds in the Cyclades were going to be too strong for safe sailing for the majority of our ten-day charter. 

We needed to make a decision: Prepare to be stuck somewhere in the Cyclades or escape… 

Patrik knew these clients as they were returning from a previous charter season, and knew for a fact that they liked to sail. So, the decision was to escape the Cyclades, and the best direction to head according to the wind was toward the Dodecanese Islands. 

Syros – Embarkation

The clients arrived in Syros with weather too strong to sail. We waited for the wind to subside in Finikas harbour for about a day and a half, and although we were stuck, we made the best out of the situation. The most memorable part of our (first) night in Syros was a pot-lock barbeque on the pier.

The harbour master gave us octopus, lamb, tuna, sausages, bread and even more to grill. We had enough food and wine for our ten clients, myself (first-mate), Patrik, the harbour master, and all the others from the harbour who joined the barbeque!

It was a beautiful night full of great food and a plethora of different people from different walks of life laughing and joking together for hours. And after all was finished, we went back to the boat, sat on deck together, and played card games under the stars. 

The weather was not in our favour, but it didn’t get in the way of us all having an incredible time and making the most out of an unfortunate situation.

Naxos – Kalados an Undiscovered Paradise

The logical first stop on our sailing charter journey was Naxos Island. Naxos is the largest Cyclades Island with a high number of inhabitants (for Greek island standards) and has a main town full of shops and restaurants. But Naxos, being such a large island, also has plenty of less populated areas. 

We chose to spend the night in Kalados, an extremely secluded harbor in Naxos. 

It is truly magical arriving into Kalados. We enter into a large, empty bay surrounded by green hills and farmland. There is a clear, sandy beach stretching along the water line; and, sometimes you can see (and hear) herds of goats, horses and even giant pigs strolling down the beach. 

Kalados may lack people, but what it does not lack, is food. 

There’s a family who lives in the area and they own a ton of land and livestock. They also own a trailer at the top of the hill beside the harbor where they serve fresh and delicious food. 

This place is anything but fancy, but a wise person once told me that restaurants with the most uncomfortable chairs have the best food.  

After the trek up the hill to this “restaurant” you are rewarded with homemade cheese, wine, freshly picked vegetables, unbelievable fries, and juicy goat chops (made from a goat who lived mere hours before you had the privilege of digesting it). Sorry vegetarians! 

Anyway, we all ate and drank to our hearts’ content. We even asked the owners’ if they could prepare breakfast the next morning to which they kindly agreed. So, we ate just as much the next morning! 

Full and eager to sail we left Kalados. 

Astepalia – Saint Mary’s Day

It was a long, but amazing sail to Astepalia. Neither me nor Patrik had ever been to this island, but we decided to take the chance and check it out. And what a great decision that was! 

Astepalia, although not a touristic island, had so much to offer. It was full of adorable shops, interesting architecture, and great dining and entertainment. And it made such an impact on the clients that they wanted to stay for two nights. 

Luckily, our second night was on Saint Mary’s day (a celebrated holiday in Greece). We went out to dinner together at a nice restaurant located at the top of the mountain overlooking the harbour. 

As we enjoyed our meals, a few people carrying a huge, decorative arch stood beside us. In front of the arch stood a priest, and behind the arch, seemingly everyone on the island formed in a line. 

Music played and slowly but surely each person made their way under the arch to kiss and shake the hand of the priest. 

Then after dinner myself and a few of the younger clients decided to partake in the after-hour festivities. There was a party that everyone was talking about taking place in a famous church at the top of the mountain. Of course, we went!

As soon as we walked into the church, an old woman called us into a room where she gave us tons of wine and bread before we made our way to the main corridor of the church.

The church was completely full of people from top to bottom, and there was a band playing traditional Greek music. Food and drinks were being served at every corner, and the atmosphere gave off authentic yet vibrant vibes. 

The clients and I joined hands with the locals and danced until the early morning hours. 

Nisyros – The Volcanic Island

Sailing toward the island of Nisyros is a spectacular sight. It is a small, round island that looks just like a volcano. Which makes sense since it is a volcano!

Nisyros, although one of the more active volcanoes in Greece, is a habited island. It has two harbours, plenty of restaurants, taxi services, and markets. The island is small and quiet, but has enough to entertain tourists and locals alike.

Our charter group took a taxi to the top of the island (rather the volcano) to a village along the rim of its hot center. I know two things from their descriptions: (1) it’s a super cool sight to see, and (2) the gasses coming from the volcano smell like rotten eggs.

It’s pretty crazy to think that just the night before we were celebrating in a church on top of a cliff, and then the next day we were walking along the edge of a volcano! 

Kos – Large & Lively

Sailing beside Kos you can see Turkey so clearly, as if it were a stone’s throw away. A sight that reminded us all how far we travelled since leaving Syros.

Kos, unlike Astepalia and Nisyros, is a large touristic island. Pulling into port you see tons of boats, big and small; and, a long line of restaurants, souvenir shops, taxi services and plenty of people.

Kos was the perfect place for the teens onboard to go out and have a good time. There are a lot of clubs and bars on this island, and definitely a lot of young tourists looking to party.

After our night in Kos, we needed our next stop on our sailing charter journey!

Levita – One Family Population

Levita is the polar opposite of Kos. There’s no port on this island, but there’s a large beautiful bay to moor.

Only one family lives in Levita and they have a restaurant where they serve anyone who decides to spend a night or two in the bay.

We took the dinghy to shore and we hiked until we found the restaurant. There we sat outside and had amazing local food.

This one-family island is definitely one to remember! 

Schinoussa – Dining Beachside

Our next stop, Schinoussa, is part of the small chain of islands known as “the small Cyclades”.

We dropped anchor right in front of a beautiful white-sand beach. And right on the beach, there is a restaurant and bar that always plays great music and serves delicious food and refreshing drinks.

Some of us took the dinghy to shore, others swam or took the paddle boards. But, sooner or later, we all made our way to the beachside restaurant.

After a long sail it was nice to relax beside the water, eat, drink and laugh together.

Then to top it all off, Patrik took myself and the four adults on a dinghy-ride to see the perfect sunset!

Paros – Old Town, New Vibes

The main village in Paros is always a great stop during a sailing charter! This old town is full of little side roads, paved with stone, and surrounded by white clay buildings. It is easy to get lost walking through the village, mesmerized by all the colourful shops, beautiful architectures, and delectable smells.

There is something about Paros that feels like going back in time, while simultaneously, experiencing something modern and lively.

We had a relaxing night in Paros. We enjoyed dinner together at a wonderful restaurant located down a little side-street. The food here, like many places in Paros, was a bit different compared to traditional Greek cuisine. But equally as delicious!

This change in food and atmosphere was just what we needed after many long sails! 

Syros – Journey’s End

After a long and incredible week, we finished where we started…Syros. To recreate our first night in Syros, we went to the butcher and the market to get a bunch of food to grill and bottles of wine to drink. Once again, we barbequed on the pier and ate until we couldn’t eat anymore! 

Over 300 miles later, we finished our sailing charter with new memories and new friends.