This is a challenging trail for adrenaline and history lovers. The routes starts in Smokvica and continues towards Čara. It then climbs the road above the bay and beach of Pupnatska Luka all the way to Pupnat, the smallest and one of the oldest settlements on the island. Crossing over to the northern coastal part of the island along the steep descent on a winding road to the bay and village of Kneže, the route continues along the coast to the village of Račišće, where it follows the gravel road next to beaches of Vaja and Samograd all the way to Babina bay. From there, it takes an asphalt road passing by picturesque and peaceful bays of Rasoha and Blaca and continues to Prigradica. The route will take you along the road from the promenade towards Blato, a village in the hinterland of the island that features a vast field and the famous dry stone wall terraces. From there, it continues to Smokvica. Just before arriving to Smokvica, at the local cemetery, there is the oldest church of this area, St. Cyprian’s Church dating from 1329.