The Napoleonic trail (Strada Vicentina) is the must-do run in Trieste. This old road, now a wide gravel path closed to cars, runs along the hills above Trieste, with fantastic views of the city and the waterfront. It’s a popular place for a stroll or a run. There are numerous marked viewpoints along the way. This 8 km (5 miles) out and back route is mainly downhill headed north and uphill (4-5% grades) headed south
Start at the Obelisco monument at the south end of the path. Head north along the Strada Napoleonica path for 4 km, enjoying the views. At the 3 km mark, you’ll see the modern Sanctuary Monte Grisa viewing platform to your right, and pass several observation decks. At 4 km, reach the southern end of the trail. Retrace your steps for the return.
Loop Option for Return: For variety, you can take the Sentiero Niccolò Cobolli – Žlanjiva for the return. To access it from the southern end of the Strada Napoleonica, take Strada Vicentina and then the road to the Monte Grisa parking lot. Join the trail at Monte Grisa. At the northern end, you’ll have to take the SP35 for 1.5 km (busy road but decent shoulder) back to the Obelisco. There are other trail running options in this area.