You can easily check the routes I've ridden in Marche region by clicking up the image below.
Ancona on the flats
Along the coast in northern direction, the roads are almost dead flat. These roads can be pretty trafficked at times, but if you're looking for a flat ride with a nice breeze from the sea, this is the route for you. Ensure you keep yourself next to the sea, avoid getting on the A14 highway. The route below ends in Senigallia, but you can continue the route towards Fano, the road is the same SS16, and it continues, dead flat.
ancona and the surrounding hills
The Ancona region is not mountainous but you can find some really nice hills, steep ones as well. One nice short route is the climb to Agugliano.
Another great hilly route is when you take the road from Ancona to Sirolo. You'll have plenty of superb views to the Adriatic sea, and nice climbs, not too steep. If you continue towards South along SP100, you will find again a flat road that follows the coastline.
Monte Conero is one of the great climbs of Ancona. 2,7 km with average of 11% gives you plenty of nice views to the Adriatic Sea. The climb includes some steep sections of around 20%.
If you are looking for a hilly day in the saddle, the surroundings provide you with plenty of hills, some steeper than others. The route below includes mostly hills with 10% gradient, but includes some steeper with an average of 14%.
The mountains are located to the southwest from Ancona. There are many beautiful serpentine roads in the surroundings of Genga. However, you might want to check out alternative routes, just in case, since landslides occur in this area and there might not be a road left. Below a 180km route around the Genga area. I got lost a couple of times due to a land slide, and found myself on dirt roads a couple of times. But it was all worth it. The climb up to Poggio San Romuald and the road from Castelplanio to Trivio was really nice.
Finally, you can explore the Strava Segment explorer for more segments or browse for the global heatmap.
In bocca al lupo!