Tolentino, like Macerata is a mediaeval walled town perched on top of a hill so that it had excellent defenses. Tolentino is not far from Macerata and can be reached by local train. It is in the southern central region of the Marché. The shrine of Saint Nicholas of Tolentino is in the town, which makes it a centre for pilgrims who hope for a miracle, Saint Nicholas is the patron Saint of Holy Souls. Pilgrims from all over Italy visit the shrine. The Basilica of Saint Nicholas is the Gothic Capellone di San Nicola, complete with masterpieces from the fourteenth century.
Another architectural wonder of mediaeval times is the clock tower which is one of the strangest I have ever seen as it has multiple faces, one of which shows the phases of the moon. You can stand looking at the faces for some time, trying to work out their purposes; it’s great if you like
The Castello della Rancia is the castle which began its existence as a Benedictine abbey in the twelfth century, but was changed into a castle when it fell into the hands of the family who ruled the region, the Da Varanos, in 1357.
The Battle of Tolentino was fought outside the city in 1815, during the Napoleonic Wars. when the King of Naples, Joachim Murat was defeated by the Austrian forces commanded by Marshal Bianchi. Every May there is a re-enactment of the battle which is quite spectacular to watch, if you happen to be in the neighbourhood.
The old city is approached through an ancient gate and immediately you go through it you feel as though you have been transported back in time. You can believe that you are in mediaeval times.
The old city of Tolentino has cobbled streets and is built into and on the hill top. Its streets wind interestingly and there are lots of trattoria where you can sample the traditional fare of the Marché region. The fresh vegetables when drizzled with locally produced olive oil are a delight when grilled and served with crusty bread. As in Greece, there are olives, cheeses and Italian meats, including Parma ham and mortadella of course. Some good souvenirs are the olive oil, truffles and a whole Parma ham.
Tolentino is also home to the International Museum of Caricature and Humourwhich is in the Palazzo Sangallo. It hosts a biennial International Festival of Humour, so although it has its roots firmly in the past, Tolentino is very much a part of the modern world.
The surrounding countryside is beautiful and full of wild life including wild boar. There are mushrooms in the right season too and of course, almost every part of Italy has a food festival. Close to Tolentino there is a mushroom festival which is a gastronomic delight if you love edible fungi!
I think that the Marché region has a lot to offer and in my opinion it is better than Tuscany which has become a tourist trap. The mediaeval hillside cities of the Marché are well worth visiting!