TripAdvisor Sailing Greece – Best way to visit Greek islands

Reviews for a private sailing cruise in Greece

We sailed on the Andreas for 7 days with Ilias as our skipper. This trip was AMAZING!!

We worked with Apostolos to book the trip, he was extremely helpful and able to answer all our questions (even considering the time differences, he always responded very quickly). I knew based on how organized he was that I was dealing with a solid company.

When we got to the boat, we were met by Antonis (owner) to go over our paperwork and to discuss what to expect during our week on the boat. He was extremely professional and wanted to make sure we were happy and would enjoy our time sailing.

Our skipper was Ilias – we didn’t have a concern all week thanks to this guy! He was very professional regarding sailing (he could back the boat into the dock between 2 boats seamlessly, I don’t know that I could park a car that well!) Spending a week on a boat with someone we just met was not a problem at all – Ilias was friendly, always making us laugh and sharing some amazing stories about his life and about sailing. He took us to great restaurants, told us interesting things to see on each island, and was always willing to go along with whatever we wanted to do. 

The trip itself was spectacular! Having never been to Greece before, I wasn’t sure what to expect – the Small Cyclades far exceeded my expectations. The water was beautiful, we stopped at various coves throughout the week to swim while we were sailing between islands, very remote and pristine, even more impressive than pictures I’ve seen. The islands we visited were really interesting to see – a few were very small with just a few restaurants, others were bigger with a lot of activity, but all of them were very authentic and interesting (I had originally wanted to go to Mykonos or Santorini but having seen the islands we went to, I know I would have been disappointed with how busy and touristy these 2 islands were). The food was amazing, the people were friendly and the landscape was spectacular. 

I can’t say enough good things about our experience with Greek Water Yachts – if you’re considering a sailing trip, this is the company to use. Right from the beginning of planning this trip, they were extremely helpful, when we arrived they made sure to greet us and make sure we understood that our only responsibility was to enjoy ourselves, and for the next 7 days that’s exactly what we did.

When my husband first suggested we add a 4-day sailing trip of the lower Cyclades to our 30th wedding anniversary trip to Greece, I was a little apprehensive. But he persevered and I’m so glad he did! Apostolos was great to work within our planning and answering all of my extensive questions prior to our trip, and even sending me pictures of the boat interior! Our skipper was Dionysis and he made our trip so memorable. Our boat was Rafaella – plenty of room. Since it was just the two of us, we were able to use the 2nd bedroom for our luggage. The first and last days were our longest sails. I started to get sea sick the first day and Dionysis had me stand up and look straight ahead. It worked! I learned what I needed to do and wasn’t sick during any other sails. He would suggest great restaurants on the islands we stayed at each night. We chose to have Dionysis eat with us each evening: we enjoyed his company and he was great at suggesting meals for us to try. All of the restaurants served delicious food, but I must say, on the island of Iraklia we ate at a very small outdoor restaurant named Akathi – amazing! I had Pastitsio – the most wonderful flavors! Cats were our friends this evening, as in a lot of Greece! Koufonisia was the most beautiful island we visited during our sail. We took a hike around part of the island and saw beautiful coves and topped off by a breathtaking beach and bay! There was a nice shopping area on Koufonisia as well. On our last full day, Dionysis took us to an inlet off of Naxos where we snorkeled (not a lot of fish to see in the Aegean :( and swam into a water cave). It was May so the water was chilly, but we got used to the temperature quickly. The best part was that Dionysis took video of us snorkeling and lots of pictures. In May it could be chilly while sailing, so make sure to bring jackets. A memorable trip that we will remember forever!!
sailing koufonisia with Greek Water Yachts from Paros
We had the best family holiday ever with Dionysis as our skipper for the week sailing around the Cyclades. We shall never forget the fun and laughs we had with Dionysis as he let our kids sail the boat whilst we sang along to his playlist and trying to spot dolphins! The communication I had before the trip was super efficient and friendly and I felt confident about the choice we had made. I can’t rate this small company highly enough as the experience you will have is all about the skipper and as Greek water yachts only employ a few skippers you can be sure of a successful trip. We would love to do this trip again and please don’t hesitate to book with them!
July 12, 2018

My boyfriend and I enjoyed a six-night trip sailing Paros-Schoinoussa-Koufonisia-Amorgos-Irakleia-Naxos-Paros. Our skipper, Kostas was very knowledgeable and helpful and we enjoyed several memorable dinners on the islands with him and appreciated his recommendations of fine restaurants. The waters were relatively calm and the sailing was easy and relaxing. We really enjoyed all of the islands for various reasons and they all had something to offer including amazing views, great beaches and the experience of the Greek Islands that we were looking for. If you are interested in a sailing trip, Greek Water Yachts was very easy to work with, reasonably priced, with a clean and modern boat and experienced skipper. A trip to remember!


greek island sailing review catamaranMy sisters, nieces and I had the most incredible time in the Western Cyclades of Greece sailing with Captain Nikos Biblis from! The sailing was spectacular, the waters of the Aegean Sea are gorgeous, the islands were breathtaking, and the people were amazing!


sailing greek islands reviewsJust returned from an amazing honeymoon hosted by Greek Water Yachts! Such an amazing part of the world and the team at GWY took great care of us. From booking to onboarding and the sail itself with our skipper Dionysis was all a very pleasant experience. It’s a great opportunity to get away from the tourist areas and truly see the small Cyclades. They are very accommodating and adapt to your specific needs. Highly recommend!


tripadvisor honeymoon
We sailed with Greek Water Yachts for our Honeymoon and loved every second of it. It was a unique way to experience the Greek islands that will make you laugh at those who only understand the Greek Islands as Santorini and Mykonos. The islands we went to were local, intimate, and each had its own character. Words can’t describe how great the food was throughout our trip. Each restaurant sourced their food from local lands/waters and thus each unique flavors and specialities. If you are a foodie you will not be disappointed. The boat itself is very safe, modern and comfortable. There is a rustic element to living on a boat for 6 nights but nothing beyond what should be expected. We were able to stay well rested, fed, and showered using facilities. We were just 2 people so your experience might be different if you plan to sail with a group of 4 or 5. It stays warm at night so if you typically sleep with the AC on full blast then I recommend you condition yourself to warmer sleeping prior to this trip. Our Captain, Kostas, was excellent. He is a very experienced sailor who can easily operate the whole boat by himself in any condition. He was glad to teach me aspects of sailing to let me feel like I was contributing, but then could take back over when I just felt like relaxing. His recommendations on things to do/places to eat in each port were spot on. Our schedule was Paros – Schinoussa – Koufonisia – Amorgos – Iraklia – Kalantos (Naxos) – Naxos. This was completely dictated by the winds so don’t go into this trip with a set itinerary in mind. We just knew we wanted to experience the Minor Cyclades and let Kostas take it from there. One concern we had going into this trip was the dynamic of being on a Honeymoon while being in close quarters with an additional person (Kostas). This turned out not to be an issue at all. Kostas did an artful job of disappearing at all the right times. When in port he would stay off the boat allowing us to enjoy a late night glass of wine and when anchored during the day he would retreat to his cabin while we enjoy a private swim. My one recommendation – don’t bother with the provisions list. It is nice of them to offer the service but the grocery store is literally next to the Marina in Paros. I think it would be easier to shop in person after chatting with your captain and seeing what supplies are left from previous guests.