Taking Topdeck | Greek Island Sailing

Late last year when I was trying to decide which tour to take with Topdeck, I vividly remember yearning for a chance to see Greece. When I saw that Topdeck offered three days sailing through the Greek islands, I couldn’t throw my money at them fast enough. Three days sailing under the Greek sun seemed like the perfect mode of transportation for me.


Journey to Greece

Us Topdeckers began our journey by heading from Italy to Greece on an overnight ferry. At this point in the Topdeck trip, discovering what kind of accommodations we had was always a fun surprise, and this was no exception. The ferry exceeded all of our expectations, and we had a really great time relaxing and exploring the Anek Line. The weather was absolutely beautiful, and a few of us stayed out on the deck for a majority of the day.

One fascinating thing about our ferry ride was the passengers on board. As it just so happens, a couple hundred Hells Angels bikers decided to take the ferry as well. This amused me to no end. I observed them as they all lovingly greeted their friends from near and far with hugs and clapped handshakes. It was just a bunch of teddy bears in black leather – that’s all it was. It then became my main mission in life to meet a few of them. Luckily, my opportunity came when we docked in Plateria the next day. I waltzed my little self up to a table full of Hells Angels and said, “English?” The man with the handle bar mustache and leather vest looked at me and said, “I’m from Santa Monica.” And thus began the most interesting conversation I’ve had in a while. We chatted for a bit, and one said that I looked like his future ex-wife. They were just as I suspected – a bunch of characters, but extremely nice.


Meeting our skipper

As we made our way from the ferry to our docked sailboats, we got to meet who our skippers would be for the next three days. The skipper of our sailboat was named Demetri, and he probably had the driest sense of humor I’ve ever encountered. I loved it. As he took us around the sailboat showing us our rooms and safety features, he would say in his Greek, monotone accent:

“Here’s the life jackets. Don’t use them unless drowning”

“Here are the forks. Don’t take the forks.”

Over the next three days, my sailboat group won him over, and he gave the nicest speech about what great crew members we were. Then mere hours later we hid the forks throughout the sailboat and wrote a map on how to find them. I don’t know if he still likes us or not…


Sailing to Torre a Mare

Sailing through the Greek islands was a lot like living in paradise. We would wake up, eat some breakfast, put on our bathing suits (or togs as the Kiwis would say), and get out on the water for the day. We easily got into a rhythm of living at sea and enjoying the waves. In between our sunning, eating, and sleeping, we would also have swim stops at some gorgeous coves and islands across Greece. I instantly knew that the next three days were going to be fantastic.

Our first port to dock in was a pretty sweet restaurant right off the water. It was actually kind of empty because apparently the Greeks don’t vacation until July and August. It was beyond beautiful, however, and the serenity was much appreciated. Phoebe and I went walking down the empty, gravel roads and discovered an open patio restaurant that served little ice creams. Later we had dinner at another open patio that overlooked a sunset and our dock. Every time I opened my eyes, I would discover something new and incomparable about Greece.


Sailing to Petriti and Plateria

The next two days were filled with more sun, more water, and more laughter. We would be out on the sailboat all morning and mid-afternoon, and we would dock by early evening. The evenings were filled with wandering the tiny fishermen towns and discovering outdoor markets and small churches. We also got very competitive in our card games. It was so peaceful to just sit outside in the nice breeze, drink a refreshing tea, and all talk about the day.

While docked in Petriti, we were introduced to Greek dancing by the two owners of a small, yet delicious restaurant right on the water. They taught us a few dance numbers as well as impressed us with their own mad dance skills. They danced around a ring of fire and picked tables up with their teeth. I’m pretty sure I yelled Opa at least 100 times that night.


My final thoughts

Overall, sailing through the Greek islands will probably stand as one of my favorite travel memories with Topdeck. There’s nothing better than being enveloped in the sights and sounds of Greece all while being surrounded by great company. Greece was relaxed, beautiful, friendly, and beyond all expectations. After having a rigorous schedule of seeing major cities with Topdeck, sailing came at a perfect time. The simple life at sea was just what I needed to catch my breath – and to also have my breath taken away. For our last evening together while sailing, us Topdeckers sat out on the dock in Plateria and let Greece’s sunset overwhelm us. It’s something I could never forget.


What I ate while sailing:

  • Tzatziki – This was possibly the best thing I ate in Greece. I couldn’t get enough of it, and I probably consumed my weight in it. It’s a dip that’s made out of Greek yogurt, cucumber, garlic, olive oil, dill, and red wine vinegar. It’s divine.
  • Pork Souvlaki – It’s delicious meat served on kebab sticks. I mean, I really don’t know how you can go wrong with this.
  • Snapper – Because I was in a Greek fishing town, I figured this would be the best place to order fish. Oh man, was I right. The snapper was so fresh and cooked to perfection. Demetri, however, told me that the best part of the fish was the fish’s cheek. Fun fact – it wasn’t.


Only one more article in my journey across Europe with Topdeck! Last two stops? Athens and Mykonos!

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Hi, I’m so glad you’re on my site! My name is Meagan, and I write about my traveling adventures and finding beauty in each day. For more info about me, click here!

Meagan Tilley

I believe that every day is a day that matters – even just enjoying the little things. Whether that’s traveling to the top cities across the world or binge watching Gilmore Girls. To read more, click the About Me page!

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  1. Ang

    Hey ya,
    I’ve just finished a 21 day Topdeck (Eastern Pathways) and also had Demitri as our skipper. I know exactly what you mean about his sense of humour. Our sail dropped and untied so we had to climb to the front to get it back in place. Radioed Demitri and told him “I could not be happier” in a very monotone voice was his reply.
    I would do it all again! Such an amazing experience 😀

    • Meagan Tilley

      Hahaha!! I can totally hear him saying that! How hysterical. He was such a good sport – just very …. hahaha dry. I wish I could go back sailing through Greece. Are you having withdrawals too?

  2. Erin

    Hi Meagan,
    I’m looking at doing one of Topdeck’s 7 day sailing trips around Greece. It sounds like you had an awesome trip and I was wondering if you could answer a few questions for me since I haven’t seen very many reviews online.
    How much partying were people doing? I’d prefer a trip that’s a little more subdued than it sounds like a lot of the Topdeck bus tours are.
    Did you have breakfast and lunch on the boat? Was it pretty good food?
    Were there planned activities once you docked? Or are you pretty much on your own for dinner and sightseeing?
    Was there any part of the trip that wasn’t what you were expecting or wasn’t as good as it could have been?

    • Meagan Tilley

      Hi Erin!
      Those are all really great questions. I’ll just jump right in:
      – One thing I’ve found true about group travel – you’ll always find someone who’s at your speed. Everyone “parties” at different levels. I liked to go out and have fun, but I didn’t like to go nuts. I definitely found others who were the same way.
      – We did have breakfast and lunch on the boats. We picked up groceries from the local markets and used the boat’s basic kitchen to cook. Topdeck will also provide lots of goodies too.
      – We generally docked around 3-ish, and we had the rest of the afternoon/evening to explore the town. By evening there was some form of dinner and entertainment provided. Those were a lot of fun. They also provided opportunities to shower and clean up. Granted, we all looked pretty rough throughout. Sailing is a low maintenance life.
      – To be honest, the rooms/beds weren’t the best. However, you’re rarely in them. I found that it didn’t matter much to me. A few of us even slept up top on the sail boat under the stars.

      All in all, sailing was one of my favorite parts of the trip. Let me know if you have any other questions!

    • ronald trieste

      Hi Erin! Did u go on this 7 day sailing trip? I’m planning to do same in August. Like you, I was having a hard time looking for reviews on this specific Topdeck Greek Sailing trip. I would surely appreciate your inputs if ever you did go. Thanks!

  3. ronald trieste

    Good read and awesome photos. Thanks Megan!