A spectacular itinerary exploring one of the most beautiful parts of the entire Tyrrhenian coast. It is rather difficult as the path, excluding the first 7 km and the last 10 km, is one of continuous up and down. Some parts are very steep, however only briefly. Worth noting is a segment of about 3.5 km on very rough dirt that requires an all-terrain or mountain bike. The near total absence of traffic between Porto Ercole and Porto Santo Stefano and the extraordinary natural environment with its sea views render this itinerary a highly interesting one for bikers and excursion cyclists.
Departure and arrival point: Orbetello
Incline: 450 m
Type of road: mixed
Length: 38.4 km
Departure is from Piazza Mario Cortesini in Orbetello, following the signs for Monte Argentario and Porto Ercole. Ride on the bike path that follows the S.P. 161 right in the middle of the Laguna di Orbetello. After 2 km turn left in the direction of Porto Ercole and Cala Galera, taking the S.P. 2 for Porto Ercole. You cross the fork for Cala Galera and after a slight incline you come to Porto Ercole (6.2) and its small port. The road skims the entrance portal to the historic town center, the Don Pedro hotel, and with a sprint uphill the S.P. 66 "Panoramica Porto Ercole" leaves the town and immerses itself in the countryside, among pines and Mediterranean shrub, offering a beautiful view of the coast and Isolotto. The road climbs gently for about 4 km, until reaching a hilltop (10.5) where a very steep downhill run begins.
A few hundred meters later, in front of the barricade of the old road (closed due to landslide), you continue to head downhill until reaching a fork: keep right towards the parking lot, ignoring the signs for "Il Pellicano". You’ll cross a short dirt track and then head up a steep asphalt ramp which then returns to dirt track after 500 meters and proceeds less steeply up to the hilltop (11.9). You begin to descend, bypassing Punta Avvoltore. Soon after the wide but rough road begins to ascend again; at this point the view of the coast between Punta Avvoltore and Punta di Torre Ciana is superb.
After about 1.5 km uphill you reach a hilltop crossroads where you head straight on downhill on a rough track. At the next crossroads (14.4) you again keep straight, returning again to an asphalt road: continue on downhill for 2.8 km and then the road becomes immersed in thick Mediterranean shrub, with many arbutus and mastic plants. Soon after, the view of the coast widens onto the Torre delle Cannelle and the Isola Rossa while the road climbs gently. Then the path turns sharply towards the interior only to then return to the coast overlooking craggy rocks and the Torre di Capannelle and, further out, the Torre Ciana.
Circumventing the promontory from which Isola Rossa and the wide Cala dell'Olio (21.5) can be seen, the road turns sharply toward the interior with a very difficult stretch of over 1 km, characterized by steep and narrow hairpin turns. Continue on uphill following the level curve, where you’ll find it less wild—the shrub giving way to olive groves and low stone walls. Continue to ascend for about 2 km until you see Capo d'Uomo (24.8), then after reaching the top head downhill for 1 km to a crossroads (25.8) where you turn left, following the sign for the S.P. 65 "Panoramica" (continuing straight on you head downhill rapidly to Porto Santo Stefano).
The long and pleasant descent on a smooth asphalt road offers a lovely view of the coast and Cala del Bove, the small island of Argentarola, and then Cala Grande. Having arrived at Porto Santo Stefano, continue on to the roundabout (36.3) where you head in the direction of Porto Ercole and Orbetello on the S.P. 161 of "Porto Santo Stefano". There’s a small uphill segment and then it’s downhill towards the coast. Passing through Pozzarello (37.8), continue without difficulty to Orbetello (45.5), with the last 2 km on the bike path in the middle of the lagoon that was taken at the start of the journey. The tour ends where it began in Piazza Mario Cortesini (46.3).