Adventure, Destination, Europe, Greece

Tales of Adventure: Sailing the Greek Islands

You never know what you might find in your spam email box. I would suggest checking it every once in a while, making sure nothing interesting has been relegated to this reject folder by accident. I found such an email there once and it led to a great bucket list adventure. It was an advertisement email from Gap Adventures, and it was pushing a last minute promotion on Greek islands sailing trips. With so many amazing places to visit in Greece, I clicked the link.A few weeks later, I was on a plane to Athens, Greece. I left my tiny little apartment in Paris at 5:00 in the morning, caught a taxi to Charles de Gaulle airport, and was on my way. I had no idea what to expect. As I was a solo traveller, my only hope was that the other people on the sailboat weren’t completely intolerable. Ten days on a boat with strangers could be considered a bit risky. Thankfully, I had luck on my side.

Our boat consisted of myself, the Irish captain Vince, his “first mate” who was an Australian guy living mostly in Thailand and Cambodia, and two other girls who were coincidentally also from Australia. And what a group it was. We sailed in a loop, from Santorini to Santorini, hitting other islands along the way. I had never been sailing before, but after the first few days I found my sea legs and the motion sickness died down. Eventually we found we were feeling more sick on land, and had to get back on the boat to feel like the earth wasn’t “moving”.

The itinerary had us hitting the islands of Amorgos, Korfinisi, Naxos, Paros, and Ios before heading back to Santorini. We did spend several days in Mykonos due to unfavorable weather for sailing, and that island deserves a post unto itself. What shenanigans. I would truly say there was no better way to see the Greek islands than by sailboat. Our schedule was ours to plan, the group was small, and it felt like a much more personal experience than would ever be possible on a huge cruise ship. Plus there’s the joy of the actual sailing!

There are around 6,000 Greek islands, if you count all the teeny tiny ones. Roughly 200 of these are inhabited, and of the 7 we experienced I found that each had its own, particular flavor. Many islands were far more mountainous than I had imagined, with white buildings dotting the landscapes and small winding roads on which there appears to be no speed limits. In fact all road rules seem to be more suggestions than actual rules. Yet somehow it’s impossible to not fall into the laid-back vibe. Not in a Caribbean island way, but in a groove that feels distinctly Greek. Part of that I’m sure is due to the people. The locals we encountered were by far some of the most friendly people I have ever met, and so willing to share part of their culture and lifestyle with us visitors.

One click, and this whole other world was opened up to me. Not bad for a spam email. That one click and subsequent holiday is the very reason I ended up in Australia almost a year later. But that’s whole other story…

Featured writer: Amy Lynne Hayes

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11 thoughts on “Tales of Adventure: Sailing the Greek Islands

  1. Jaclyn says:

    I studied abroad in Greece and had the chance to see a few of the islands, sailing them like you got to do, would have been amazing! If I go back I’m definitely doing this!

    1. I would highly recommend it!! It was such a cool, unique way to see the islands, and more personal than commuting via ferry or on a larger cruise. It was a very special experience. 🙂

  2. Great photos, Amy. What size was the boat…was it “full” with 3 passengers? What was the cost?

    1. Thank you! So glad you enjoyed them :). The sailboat had 5 cabins, allowing for 8 passengers plus the skipper. We were lucky in that there were only 3 passengers, the first mate, and the skipper, so we each had our own cabins. I booked during a promotion (Gap Adventures is the company) but I believe the usual price is around $1500 USD. Once you get to Greece though, it is extremely affordable. The bigger, more popular islands are more expensive, but overall nothing shocking. Hope this helps, and if you h ave any other questions please shout! Oh, and my skipper’s name is Vince – if you look into this trip further, see if you can get on either his or Dave’s boat. 🙂

      1. Janet says:

        When did you go, was it this year…..how was the weather?

        1. I was there in May of 2011. It was still a bit cold when I was there – very pleasant during the day, but needed jackets at night. I would recommend going sometime in June for ideal weather. It should be warmer by then, but not so hot that sleeping would be uncomfortable. 🙂

      2. Thanks for the info, Amy. Most appreciated.

  3. Doreen says:

    I’ve booked this trip, plus best of Greece, and can hardly wait for my adventure to begin! But a bit apprehensive, too, since it will be my first solo trip. Happy to hear you had a wonderful experience!

    1. You’re going to have a fabulous time!! Did you book with Gap Adventures? If so, if you just so happen to have a blonde Irish skipper named Vince, tell him I said hello! 🙂

  4. Daniel says:

    Hi Amy! I’m thinking of doing this trip as well but I am surprised that it doesn’t include any meals, not even breakfast or so… How did you organize the meals, especially breakfasts? Did you buy at the islands and then cook it back at the boat or did you always eat at each island you stopped?

    Thank you!!

    1. Amy Lynne Hayes says:

      Hello Daniel! I can’t recommend this trip enough – it’s still one of my all-time favorite experiences. This particular trip didn’t include any meals, but what we did is each contribute to a community pot, and bought groceries from that when we were in port. We did a mix of eating on the boat and at restaurants on land, and for the most part it was very inexpensive. The more popular islands like Mykonos and Santorini were pricier than the others, but some of the rest were as little as 8 euros per person. I think there may have been a lunch or two included during some of the tours, but it’s been a little while and my memory is fuzzy on that account. One thing I do remember clearly is never being stressed about food! Hope this helps, and let me know if there’s anything else I can do to help! 🙂

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