Top Pylos Sailing Trips

A fantastic day sailing with Captain Nikos, who took us to some great spots to snorkel, including a small shipwreck. Not a lot of wind but we did manage to get the main sail up and hit 7 knots. Highlights were swimming ashore to have a drink at a beach bar, Nikos recommended one which was a short walk from the beach but a hidden gem. We also swam in Voidokilia beach which was absolutely stunning.

Our family of four spent a wonderful 6 days / 5 nights sailing with Nikos. His knowledge of the region and getting to spend time with him added to this memorable trip. I enjoyed learning how to make Greek coffee and kayanas, and sampling olive oil. We especially loved visiting many small bays on Sapientza island.We quickly found a rhythm of wake up, swim, coffee and breakfast, sail an hour or two, long swim, lunch, nap, swim, coffee, swim, sail an hour or two, clean up, dinner, sleep, repeat. I already miss being on the boat!

Quick and easy booking! Ina and Peter are great hosts. It was a wonderful sailing trip with beautiful memories! Thank you very much!

We had an incredible experience sailing with Peter and Ina 🛥️ Not only did they offer their exceptional customer service making fresh coffee and providing fruit but they hung our aerial silks for a photoshoot! I will remember this trip for my lifetime! 👏🏼

We spent a beautiful 4h cruise with Peter and Ina, two lovely people! The boat was beautiful, the fact of having sails allowed to feel the calm of the sea... The fruit platter was delicious!! We highly recommend you discover this beautiful bay and even more with Peter and Ina. Thank you very much for everything ☀️

This was our fourth daily charter with Nikos on his lovely yacht. It was, as always, a great day out. We sailed around the lovely island of Proti with various stops. Crystal clear water made for superb snorkelling. Nikos is a superb host and his wife prepared lovely Greek snacks and nibbles for the trip. Nikos bring some lovely Greek wine and beer and it makes for a super day out. We rounded it off with a lovely dinner in Marathopoli.

We had a great time on our 2-night sailing trip! Nikos was a fantastic host - he showed us some really nice spots and was happy to adjust the plans to fit our interests. He's easy-going and interesting to talk to, which made the trip even more enjoyable. Plus, the lunch he prepared was delicious! We'd definitely recommend this sailing trip and Nikos' expertise. :)

We had an absolutely amazing day with Peter and Inna! The boat was absolutely beautiful and meticulously maintained. Inna made us the most amazing seafood dinner meal with such a wide variety of different foods and local foods and homemade foods from their local farm estate. It was absolutely delicious and much more than we could ever finish. Peter was an amazing captain and told us so much history about the area and we loved learning from him. We were on a trip with our adult children, and one 12-year-old and it was the perfect day on the water. We went swimming and enjoyed every minute of our 7 hour sailing day. We would highly recommend and will do again when visiting the area.

Incredible experience! The views were stunning and the staff super friendly. We swam, relaxed, and took amazing photos. Perfect for a fun day with friends!

In September, my wife and I enjoyed a three-hour sunset cruise with Messinia Sailing, led by Captain Peter and his son, Vladimir. From the start at Kalamata harbor, their warm and professional welcome set the tone for a wonderful experience. The boat sailed along the stunning Messinian Bay, offering breathtaking views of secluded beaches and coves. We stopped for a refreshing swim in crystal-clear waters, a highlight of the trip. Onboard, we were treated to a delicious spread of meats, cheeses, fresh fruits, and sparkling wine for their vines, perfectly complementing the serene surroundings. Peter and Vladimir’s hospitality and local knowledge made the cruise even more memorable. As the sun set, the sky turned into a vibrant display of colors, capping off a truly unforgettable evening. We highly recommend Messinia Sailing for anyone visiting Kalamata

Peter and Ina were very kind and accommodating. They provided us with drinks and fruits!! The half day tour included several stops to swim, and snorkel. Peter was very knowledgeable and explained the historical meaning of the area. Their boat is very well kept and clean. Would definitely recommend to anyone staying in the Kalamata area!

Lovely day out sailing and swimming, everyone had a great time. Nikos and Lambros were amazing hosts. We'll definitely do it again. Please get a wider gangplank!!

Peter and Inna were the best! We had such a great time on the boat. They organised a private trip for us at the Navarino Bay area from Pylos port. Wines and fruits, and sailing into the sunset. Thank You for being the best hosts!

Peter and Inna at Messinia Sailing are incredible! They are the nicest hosts. They took me and my two friends on a private cruise for 4 hours in Kalamata, we stopped at a gorgeous swim spot and also swam into a really cool cave. They were nice enough to take pictures and videos of us throughout, and made sure we were having a great time! We learned a lot about the history of Kalamata on the tour as well. Completely recommend to anyone looking for a relaxing, amazing experience!

Lovely 1/2 day sail with great host Nikos . 3 teenage girls enjoyed swimming in caves and jumping in water from cliffs. Relaxed and easy, and Pylos is a pretty town to spend time in afterwards. Highly recommend Nikos and his boat.

Wonderful experience on the turquoise waters of the Mediterrannean! It was our 3rd trip with Peter and his wife, our entire family has been enjoying them so much, even our youngest (now 4, but she was only 1 year old on her first trip). I can highly recommend a trip to anyone who loves the sea!