Anchors Away! A tale of our SAil in Search of the Best Gyros…
Ahoy mateys! After our eight night sailing trip through the Cyclades Islands in Greece, we think it’s safe to say that we’re professional sailors. Ha! Joking aside… we really did learn a lot about sailing in this short amount of time and we are really looking forward to taking future sailing trips to continue gaining experience. Perhaps one day we will be able to captain our own vessel!
As with Switzerland, we had some trouble figuring out how we wanted to tackle Greece. We knew we wanted to visit a few of the Greek islands, but moving between islands is not only incrementally expensive but also time consuming. We would end up having to pay for multiple ferries, cabs to ferry terminals, cabs to airbnbs, etc. while also having to spend many hours on the ferries and commuting to and from the terminals when we could be enjoying everything that Greece has to offer.
Thankfully, one of the first people we met on our trip was a Greek man who recommended we find a sailing trip when we visit Greece. This was surprisingly difficult at first, but it turned out we were just not well versed in sailing lingo to properly search for the right experiences. We ultimately found a reasonably priced 8-night sail through the Cyclades Islands on a shared yacht. Well… it was not actually a yacht… just a sailboat. But our new sailor friends taught us that all sailboats are technically yachts, so we’ll just go with that because it makes the experience sound much more glamorous than it was.
When we booked the trip, the itinerary said we would stop in Santorini, Naxos, and Ios. We were ecstatic because this was the exact itinerary we were looking for. We were going to hit all of the islands we hoped to visit without having to take a single ferry, change Airbnbs, or repack our bags. Joke was on us though. We did not end up visiting ANY of these islands. However, this is actually what made the trip so perfect and even better than anything we could have imagined.
Instead of hitting the hot spots, our skipper, Kostis, said he was going to take us to some of the very small, local islands to give us a more authentic view into life on the Greek islands. At first, we were a little bummed we wouldn’t be visiting some of the places we had always dreamed of seeing, but we knew this would make for a much more enriching experience because we would end up visiting places we would have never known about or visited otherwise. And so began our journey to becoming sailors.
We spent the first night in Mykonos where we got settled and met our new crewmates. Here is a quick overview of who we were living with:
Kostis (top left) - Our self-taught, Greek skipper from Athens. This was his first full season as a skipper and he was the one calling the shots. He rolled his own cigarettes with one hand while helming with the other. Truly a jack of all trades.
Steve (top right) - Skipper #2! His family is originally from Cyprus and he spends his summers skipping, bouncing around from boat to boat. He lives in North London where there is apparently a large Cypriot population. It is unusual to have two skippers on a vessel this size, but Kostis was going to be on a private charter the following week and Steve was there to get familiar with the yacht before taking over.
Penny (bottom left) - A lover of the sea, Penny opted for a solo trip after her husband sustained a sailing injury and has sworn off the sea. Penny was recovering from a recent hip and knee replacements, making her overall mobility a challenge for her… and everyone. The world revolved around Penny. Expectations were high, gratitude was low.
Elspeth & Alister (bottom right) - Avid sailors who live in London. They spent many years participating in sailing races. They were the commentary we needed behind every action that happened on the ship. We asked them an infinite number of questions and they happily shared their knowledge with us. We had a great time with them and plan to catch up next time we are in London!
After the first night in Mykonos, we were off to our first destination, Kofounisi, a small island with a population of around 450. Kofounisi is part of the Small Cyclades islands, which are a group of four islands smack in the middle of the Aegean Sea. It is a popular getaway for locals, and Kostis told us he had grown up visiting this island every year since he was around five years old. As a result, he knew EVERYONE on the island. From the moment we arrived, Kostis was greeting and chatting away with every person that walked past us. In fact, his mom even appeared while we were docking the boat and Kostis was able to say goodbye to her as she was catching the ferry back to Athens. He had no idea she was even there!
We ended up having to stay in Kofounisi for two nights because the winds were too high for any boats to sail. This ended up working out for the best because we were able to get a better feel for the island by spending a little more time there. We also ended up befriending a group of Kiwis who thought it was hilarious that our names were Brittany and Justin and we were married. We thought that they were absolutely wasted, but turns out they were just Kiwis and having a really good time on holiday! We hung out with them for a few hours swapping travel stories and laughing the night away.
After two days of being unable to sail due to the winds, we were able to leave Kofounisi and make our way to our next island, Schoinoussa. This was a full day of proper sailing... and we say “proper” sailing because the waters were super choppy… which made for a good adventure. We had an absolute blast. Our skippers were surprised and a little impressed at how we handled the choppy waters. They said we definitely earned our sea legs. Honestly, we just thought everything was normal, but they ended up saying that it was quite a rough sail and that usually 75% of people get seasick in those conditions. So we guess we really are sailors then? 😜
After around seven hours, we made it to Schoinoussa. A small island with a population of around 250, there was a small town at the top of a very steep hill and around a quarter of the restaurants and shops that Kofounisi had. Within 15 minutes we had walked from one end of the town to the other while also stopping in all of the stores and bakeries… and we thought Kofounisi was small! While we enjoyed visiting this island, we’re glad we didn’t get stuck here for two days as there would not have been much to do. After exploring for a bit, we headed back to the boat for dinner and to relax after a long day of sailing.
The following day was another day of sailing, but this time in much calmer conditions. We also had a much shorter distance to cover, which meant it was swimming day! Kostis found us a very secluded bay shielded from all the winds and waves. We dropped anchor, tossed the paddle board into the water, and jumped in! The water was so clear we could see all the way to the bottom, which was nearly 10 meters deep! We also snorkeled for a little bit, but there was not much to see. After about 10 minutes of nothingness and almost calling it quits, Justin noticed an octopus making its way across the seabed. Naturally, he shared this with everyone not realizing how excited this would make Kostis who disbelievingly jumped into the water to see the octopus for himself. Unbeknownst to Justin at the time, this was a fatal mistake for the poor octopus, who was wrestled by Kostis from his leisurely walk, brought to the surface, and turned into octopus stew. We’ll spare the details of the process, but it was the freshest seafood we think we’ll ever have. From “sea to me” in around one hour. It was very tasty. But we feel bad for the little octopus who was minding its own business.
After our nice swim, snorkel, and paddle, we ended our day in Donousa. This was the island we were most excited to visit because they were celebrating the island’s patron saint the evening we were visiting. Kostis explained that this was one of the most important days on the island and they celebrate with a very large feast and party. He also warned us that we should take a nap before the party began because it would last all night long. We believed him… but we didn’t realize at the time how serious he was. He said the party started at night, but he didn’t mention that it wouldn’t start until nearly midnight! Or that there would be massive… MASSIVE… speakers blaring music all night while everyone danced the night away. We stayed up way past our bedtime watching the festivities, enjoying too much free wine, and even getting in on some of the dancing! Britt made it until around 1:15am while Justin made it until around 4:30am. Even then, the party was still in full force. It was such a fun night and truly memorable experience.
Thankfully, the hangover following the party was not too bad as we had a long day of sailing ahead. From Donousa, we started to make our way back north towards Mykonos. We sailed for another 7 hours or so before staying the night in Paros, which we also absolutely loved. Paros was more built up and touristy than the other islands we had visited, but significantly less touristy than Mykonos. It was a pretty good balance and we would highly recommend including Paros on your itinerary if you’re planning to visit the Greek Islands some day!
We ended our trip in Mykonos where we happened to dock up right next to none other than our crazy Kiwi friends again! It was such a pleasant surprise and we spent a few hours hanging out with them on their boat singing songs and swapping stories. It was a fun way to end a well-balanced sailing trip that was full of a little of everything — harsh and smooth sailings conditions, relaxing days, swimming days, Greek party, good food, and new friends!
