Right in the palazzo comunale on the piazza del comune, are some of the Roman remnants of Vetus Auximum (Old Osimo). These statues are the reason why the people of Osimo are generally called "Senza Testa" (Headless). During wars back in ancient times it was common to cut of the heads of statues...
The center hub of town life, this nice little square is a must when in Osimo :) Every evening around six locals will walk the corso (main street) which starts from the piazza del comune. All Italian towns (and even neighborhoods in big cities) have this routine every night, and even more on the weekends. It's a great way to people watch and mingle with the locals.
The only reason I'm putting this as a "must see" activity is because this street is close to my heart. I lived for a year on this street, on the third floor of the yellow row house at the end. This area of town is the Duomo district, the oldest part of Osimo. On Via del Cassero there used to be a Roman fortress in ancient times.
Via Commenda, 2, 60027 Osimo, Ancona, Italy
Good for: Couples
If your're in Osimo, definitely get a drink at Silicon Cafe, a small establishment right on the main street Corso Mazzini. Order any drink with Pineapple or Peach (preferrably with vodka); they cut REAL and FRESH pineapples and peaches and squeeze out the juice right in front of you!!! After tasting the peach and vodka, you won't be able to have juice out of a can. The bar is a big hangout for the youth of Osimo (it get's very crowded at night).
Dress Code: Anything....VERY casual
As in any Italian town, get LOST in the side streets. Just let them take you to hidden places of town and DONT use a MAP! Don't worry, Italy (especially small town Italy) is extremely safe. The only thing you may encounter are stray cats and maybe some glares from old suspicious women.
As everywhere in Italy, Osimo is surrounded by beautiful landscape. If you travel to Italy, it is definitely worth having a car to see places that most tourists don't go. This is a picture of a vineyard in the autumn along the road from Osimo to Macerata.