Thinking About Sailing in Greece? Read this First

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A Greece sailing tour sounds like the ideal vacation for many. Spending your days on the sea, exploring new islands, living that boat life. However, for many of us, the idea that we have in our heads about sailing doesn’t quite match the reality. As much as we would all love to be swept away on a yacht (at least I do) that’s not quite the reality of what you will get if you choose an adventure sailing tour of Greece. That being said, as long as you are a patient and a little adventurous, you can have an incredible time sailing the Greek islands. 

Here’s what you need to know about sailing in Greece.

Space on Board is Very Limited

When you are considering sailing holidays in Greece, remember that the sailboat serves not just as your transportation, but also as your accommodation and, well, home for the duration of your trip. This means that these small boats have kitchens, multiple bedrooms, bathrooms, and storage space all tucked in on board under the deck. It’s pretty impressive actually, but it means things are a pretty tight fit.

I noticed this the most in terms of bedrooms and bathrooms. Space is really tight and if you are two (or even three) to a room, its hard to be all in there at once. I found it easier to take turns to change and get ready and only be in the room the same time when sleeping. My biggest tip: Pack light when sailing, there’s nowhere to store big suitcases so choose a small backpack and, if you need to, leave extra luggage behind in storage. 

That being said, I actually liked sleeping on board. Once I got into my bed, everything was fine. I got to look up through the porthole and we had a fan in our room if it got too hot. Plus, there was something really relaxing about falling asleep to the gentle movement of the waves.

You Will Spend Hours at Sea Every Day

This seems like a pretty obvious point for anyone looking at sailing in Greece, but I still think it needs to be said that you will spend at least half of your day on the boat. We normally left around 8:30am, sailed for a couple of hours, had 2 hours or so for a swim and lunch stop, then sailed another 1-2 hours until we reached the next island (somewhere between 2pm-4pm depending on the day and the distance).

This may seem like a lot of time to sit on a boat, but honestly, it’s so much fun- and I say this as someone who suffers from FOMO and has a hard time sitting still. Joining a Greece sailing tour is much more relaxing than travelling by ferry or plane. You can read a book, listen to music, watch for dolphins, or even nap on the top of the deck (I fell asleep so many times). Plus, you get to visit these really epic swim stops that you would never have chance to visit on your own; hidden beaches, caves, and even a WWII plane wreck were some of the swim stops we got to explore. 

You Will get Wet and Probably Sun Burnt

You’re on a boat, so again- this should be obvious. It can get hot, really hot (hence the swim stops) but the breeze and wind can be pretty misleading too and leave you feeling comfortable until later that night when you realize you magically turned into a lobster.

Do yourself a favour and put sunscreen on regularly. Sunglasses and a hat (that won’t blow away) are also good things to have. Try to also find a bit of shade to sit in sometimes too.

Depending on how rough the sea is (fun fact, May and June see calmer waters than July and August) you may get sprayed. Now, our group only got sprayed when we sat on the front of the boat, and only when the swell was big. Personally, I loved it and thought it was a lot of fun. After all, it was hot and sunny and I wore my swimsuit all day, every day anyways. Others on the boat weren’t such a big fan and stayed more in the back where it was dry. On our Greek sailing tour, there was a cover that the skipper could put up to protect passengers from the spray as well.

Sea Sickness Can Happen, but You Can Help Prevent it

One of the biggest downsides of sailing in Greece is the possibility of getting sea sick. Thankfully, I don’t have problems with this, but a couple people on board did.

If you aren’t sure whether or not you will be affected by sea sickness, there are a couple precautions you can take.

  • Anti-nausea medications such as gravol can help (when you take them in advance)
  • There are also sea-sickness bracelets. I don’t exactly know how they work but people swear by them
  • Stay above deck and keep your eye on the horizon line. Being below deck makes it worse.

Boat Showers are an Adventure in Themselves

The bathroom and shower situation on board is definitely one of the aspects of sailing that people are curious about. Each boat is different, but our boat had an en-suite toilet and shower in each room. Though, they were tiny.

Toilets are flush, however you cannot flush toilet paper. The showers are the handle of the sink which means the entire bathroom turns into a wet room. It’s interesting for sure and, at 5’8, I was a bit too tall for the hose to stretch and had to crouch a bit. But, it worked. I didn’t shower daily since I was in the ocean every day and there was a shower to rinse off the salt at the back of the boat. Plus, some of the ports (Folegandros and Syros) actually have showers and toilets which come in really handy. 

Was it the best shower situation? No, but really it wasn’t that bad and you get used to it pretty quickly.

You Will Be Asked to Help Out on Board

If your Greek sailing tour is like mine, you’ll only have the one skipper to manage everything during the duration of your sailing trip. And it’s a TON of work. Our skipper, George, was a sailing ninja, but even he couldn’t do everything on his own. We frequently stepped in to help with little things from getting the fenders overboard, putting down the anchor, holding the ropes while he adjusted the sails, or even helping tie off the boat in port. It’s nothing terribly hard or tiring, but you do need to be prepared to step up and assist during your adventure sailing tour.

Sailing the Greek Islands is Actually a Budget-Friendly Option for Island Hopping

Seriously, it really is. Which is strange because sailing sounds like a luxury type vacation but as someone who spent 3 weeks hopping around in the Greek islands by ferry, plane, and sailboat I can promise you that sailing really is the best deal. (you can read my island hopping post here)

It makes sense when you think of it though. It’s your accommodation, your transportation, and even a bit of a guided tour and excursion when you consider the swim stops involved. So, if you have your heart set on seeing a bunch of different islands, sailing in Greece is definitely the way to go.

You’ll Probably Fall in Love with the Experience and Want to do it Again

There’s no doubt that sailing holidays in Greece are an adventure. Yes, they can be a bit rustic. Yes, you’ll probably be asked to help your skipper out when in the ports, and yes, you’ll end up covered in salt water and probably have some really interesting tan lines (raccoon eyes from sunglasses especially). However, sailing in Greece is also a once in a lifetime experience that promises to be a ton of fun. So, if you like the idea of seeing dolphins and swimming at secret beaches, of visiting small lesser-known islands, and spending your days relaxing on the water, then a Greek sailing tour is probably what you are looking for. I loved this tour so much the first time that I’ve started running it as one of my group trip options. 

Packing Tips for a Greece Sailing Tour

As mentioned above, packing light is key when it comes to sailing the Greek islands. With that in mind, here are a few tips and things I found helpful for my Greece sailing tour.

  • Backpack over suitcase. Again, small- carry on size. 
  • Dry bag: perfect for storing phone/camera/book in when on the deck
  • GoPro or underwater camera. 
  • Sunglasses (maybe even 2 pairs, one of mine broke)
  • A light coverup: something that can dry quickly and protect you from the sun. I lived my chiffon butterfly wrap by Diane Kroe (PS Save 10% on any Diane Kroe purchase with the code HANNAH10)
  • Sunscreen- and lots of it. It’s crazy expensive in Greece so your best bet is to bring some from home. Please also consider getting a coral and ocean-safe brand.

For those wondering, I di my Greek island sailing tours with Intrepid Travel. You can read more on my experience here.

Ready to Book Your Trip?

Don’t forget travel insurance!

Please do not travel without travel insurance! I’ve had to use it multiple times throughout my travels and it has saved me thousands of dollars. You can learn more about travel insurance here. If you are looking for a provider I love and recommend SafetyWing. For Canadian readers, take a look at SoNomad.

Book your accommodation

I love and recommend for accommodation. They have a range of hostels, guesthouses, hotels, and resorts. Plus, the platform has a great loyalty program that means the more you book, the more you can save. 

Book your tours

My go-to tour provider that I love to recommend is GetYourGuide. They have options all over the world and partner with local companies for everything from day trips to food experiences and even airport transfers. 

Get connected

If you want to have data while travelling for online maps or any other needs, an esim is one of the easiest solutions. I’m a big fan of Airalo and have used their sim cards around the world from Brazil to Uzbekistan, Greece to the USA. It’s really easy- you download the app, pick what country you want an esim for, and after you purchase it follow the installation instructions. You can use promo code HANNAH3326 to save $3USD on your next esim purchase. 

Not sure what to pack?

I have destination-specific guides for some countries but you can also check my travel essentials and camera gear if you are looking for some ideas. 

Looking for a travel buddy?

Check out my group trips!


  1. Kelly on September 17, 2019 at 5:14 pm

    Well, this certainly sounds adventurous! I’m pretty prone to seasickness so I’m not sure how this would work out for me haha. But I’d still be up for trying it anyways because it sounds amazing!

  2. Alex Howell on September 20, 2019 at 7:28 pm

    Excellent, I bet there are beautiful places! It would be cool if you uploaded a gallery of your entire trip!

    • Hannah Logan on September 23, 2019 at 3:50 pm

      I shared a ton on instagram 🙂

  3. GG Brewer on July 24, 2021 at 7:16 pm

    What website did you find your sailing trip on?

    • Hannah Logan on August 1, 2021 at 9:06 am

      I went with Intrepid travel! highly recommend.

  4. Cynthia Wells on April 24, 2022 at 8:45 pm

    Interested in checking out options for a few days excursion, departing Santorini or Athens on 8/24/22 and returning to Athens sometime 8/27/22. Any options?

    • Hannah Logan on April 25, 2022 at 1:49 am

      I doubt you will be able to find a 3 day sailing tour but you can look at day trip sailing excursions. Santorini has some (I have a whole blog post with ideas for Santorini) and there are a couple of small islands close enough to Athens that you could do day trips from there as well if you were looking more for seeing different islands in that time

  5. karissa luttrell on September 3, 2023 at 1:17 pm

    What sailing company did you use? We are wanting to take our daugther next June for her 16th birthday and are just now starting the planning process.

    • Hannah Logan on September 4, 2023 at 7:26 am

      I used Intrepid Travel. It’s definitely adventure sailing not a yacht so expect tiny rooms and shared accommodation.

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