Sailing in Greece with Medsailors

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Updated April 2020

A Sailing Holiday with Medsailors

This post is a tricky one to begin, purely because this Medsailors trip was the experience that started my summer in 2017 and also one that changed my whole perspective on travel as well as graduate life and what I could do. When booking the trip my best friend and I were apprehensive about living on a boat with six strangers who could have been anyone, but luckily for us, we ended up on a boat with six absolute travel fanatics who were so much fun. At the time (Summer 2017), I had just graduated from University and hadn’t started this travel blog so the images are a little lacking!

My friend Claire and I had decided that we wanted to do the Greece route as we had read some reviews online and watched some vlogs (Brogan Tate and Copper Garden), and had seen what an amazing time these people had on board. We also knew that we wanted to arrive with a night or two in a hotel at first as we didn’t want to arrive in Athens and have to get on the boat as soon as we got off the plane. Messaging Jess from Copper Garden, she recommended The Posiedon Hotel, which is literally over the road from the marina and although not a 5* hotel, it was still heaven to arrive to in the heat after getting an hour-long bus from the airport.

One of the main selling points of this hotel was the beautiful rooftop pool and bar which overlooked the beach and part of Athens. The sunsets were incredible as you can imagine, so here are some iPhone shots that we managed to get the night before our boat left.

We had decided that while we had the spare day in Athens we wanted to go explore the Acropolis, we then got chatting to some guests in the hotel who were saying it gets absolutely swamped with tourists so the best time to go visit is 9am, which is what we did. If you are going to Medsailors on the Greece route I would 100% say take an extra day and visit Athens. I think it gets a bit of a bad rep as it’s the not the most picturesque area of Greece, but you’re about to hop on a boat that is going to spend the next week taking you around the most beautiful islands so why not explore on your own for a little bit?


The Saturday morning quickly rolled around and despite a mild injury to Claire’s foot on the way to the boat, (It was horrendous, look out for sharp poles poking out the pavement!), we had arrived and we were the first ones to get to our boat, meaning we had the pick of the biggest room which is at the front of the boat. It was the size of a double bed but as it was at the bow it was kind of pointed at our feet but we didn’t really feel like it was too much of an issue. There was enough cupboard space for two of us but as usual, like most trips I tend to go on, I didn’t wear half the clothes I brought with me so if I went again I would definitely bring less clothes! I also wouldn’t bring a suitcase as it was bulky and took up valuable space in the little cabin.

After everyone else made it on board we had a little introduction from our skipper Freddie on how to do things like flush the toilet, trust me, it’s not as easy as it sounds when you’re on a boat, as well as safety things that came with staying on a boat for a week. We were soon away and heading to an Island called Perdika and as a boat we all seemed to get on really well. Claire and I were the only girls from the UK and the others were from Australia, New Zealand and were made up of a mixture of solo travellers as well as two couples of friends. Once we arrived we spent the first evening eating as a boat in a restaurant with all the others boats which was a really sociable way to get chatting to everyone. After we all went to a local bar down the road and everyone seemed to have a good night. This was one of the most memorable nights for me as I somehow lost my flip flops, fell out a window and also danced until around 3am with people that I had met just a matter of hours earlier.

My Medsailors highlights in Greece

The next few days carried on in a similar fashion and to save time and space I won’t go into detail on everyday but tell you a few of the highlights which my friend Claire and I still talk about on a regular basis.

Quad-biking on the island of Spetses and arriving at a beautiful cave and then the most Instagram worthy beach bar

Tubing in Poros and clinging on for dear life as I was terrified of falling off and being thrown across the water

The Toga party on the last night in Agistri where we smashed plates at dinner, ran out of money and ended up dancing on the bar

Watching the sunset in Hydra from a bar in the side of a cliff then heading back to the boat and playing crazy games with our boat

Swimming in the sea each morning and feeling instantly refreshed and unbelievably happy to be in that exact place at that time

Coming across a really friendly restaurant overlooking the beach in Agistri where we ordered a huge amount of food for five people and ate what felt like a feast

Jumping off a cliff from a very low point and still being absolutely terrified and shaken up by it but it was still hilarious and fun

Losing a hairbrush overboard and taking it upon myself to jump into the dingy and paddle to save it, whilst in a toga which proved very difficult

Taking naps on deck being wrapped in a big blanket and waking up whilst you were out at sea



For more information on the trips that Medsailors do have a little look on their website, I know they’re adding new routes next year and if I could, I’d spend weeks going on each one!

Have you ever been on a sailing holiday?


The photographs with @lostboymemoirs in the corner were taken by the amazing Ryan and you can find his website here.

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3 responses to “Sailing in Greece with Medsailors”

  1. The Daily Maria says:

    This trip sounds so amazing. I would definitely do it. I have been to Greece three times and I love that country. I would love to go back there.

  2. The Daily Maria says:

    This trip sounds so amazing. I would definitely do it. I have been to Greece three times and I love that country. I would love to go back there.

  3. Wow Gabs, your trip sounds so amazing. I’m definitely visiting Greece someday.

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Hey, I'm Gabriella

I post once a week covering topics such as solo travel, working and living abroad and also creating Gabriella’s Guides to places I have been. I cover topics under the following categories such as Planning and Packing, The Travel Diary, Travel Inspiration, Photo Diaries, Gabriella’s Guides and Working Abroad.

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