The Sailing Tomatoes is a music band, mainly consisted of a group of childhood friends coming from one of Thessaloniki's neighborhoods, in Greece. As kids, they have always dreamed to travel around the world playing music. It all starts in the summer of 2010, when Giorgos Moutoukias (bouzouki) and Petros Anagnostopoulos (accordion) decide to get to know the islands of Greece, playing music on the street, just to make a living for the summer. Skiathos is their first destination, where after a few days Philippos Seinkman (acoustic guitar) joins them. The three of them play together songs they like, however, while traveling, they also find the inspiration for creating their own songs. In early August, they meet with Denis Dowling (vocals), in Ios.They jam together and give the promise to meet again. Denis is a skipper so, the day after, each one leaves Ios; Denis follows the call of the sea, the other three continue their journey to the islands. In (the middle of) September, Denis joins them in Thessaloniki, where they all together write a few songs. They come up with the music, he adds the lyrics. Their next destination is Zagorohoria, where Vangelis Domanos (percussions), another childhood friend, follows them in their musical journey. By the middle of the winter, in Athens, Theodoros Moutoukias (acoustic bass) becomes part of the band as well. Looking for a name to give their group, they inspired by a play on words and they finally name the band Sailing Tomatoes. In May 2011, they record their first album Δρόμος/ Dromos, at Sofita Studios, in Athens. A summer full of new journeys and music is about to come, before they return once again at the fold, Thessaloniki, where they meet with Dennis just before he leaves for the U.S. . The band stays for the winter in Thessaloniki. Orfeas Kappa (clarinet), the newest member, officially joins the band there. They had originally met Orfeas in Volos last spring and saw him again at Heraklion of Crete and Syros. Their friendship became stronger and they played for the first time together in Naxos. In May 2012, the Sailing Tomatoes record their second album Ψιχαλίζει στα παλιά / Psichalizei sta Palia, at Shellac Studios.

Since then, the Sailing Tomatoes keep on busking 'n' traveling.