Here’s watcha wanna do, watcha wanna do is this:
Go to Farmer Shop on Via San Francesco n. 4a in Assisi, where you can stock up on prosciutto and a variety of different salami, all made from an heirloom breed of pigs raised on a farm right outside of town, and some amazing local cheeses (try the aged sheep wrapped in fig leaves). Pick up some of their freshly baked bread, as well. And finally, the kicker, a bottle—or two—of their organic, unfiltered, unpasteurised, bottle re-fermented beers from the San Biagio estate (ask them to get you the chilled ones they keep in back.)
From there, pass over to the other side of the Piazza del Comune to Il Mercantino greengrocers on Via S.Gabriele Dell’ Addolorata n. 4 for some fruit to snack on (anything marked “nostrali” is grown locally, so try some seasonal Umbrian produce).
Finally, stop in at Pasticceria Sensi on Corso Mazzini n. 14 and choose some of their freshly-made pastries (and pick up some water).
Now, take a look at your Assisi map and find Via San Benedetto, which begins about a kilometer from Porta Nuova off the main road 147, passes quickly through a residential area outside of the historic center of town, and begins to switchback up the slope of Mount Subasio. There are periodic signs for Il Monastero di San Benedetto along the road, and you want to follow those. About 6 km up, you get to the newly renovated but closed monastery on the right.
Now, of course I would never condone hopping the fence into the monastery, as that would be illegally trespassing. Which I would never condone. But, let’s say, hypothetically, that one were to hypothetically step on the low stone wall to the left of the locked gate and hypothetically swing their legs over the wrought iron fence (being hypothetically careful to not hypothetically break their precious bottle of beer in the process).
Inside, one would hypothetically discover one of the most peaceful spots around…the centuries-old stately stone monastery surrounding by woodland and a sunny paved patio looking out over the valley below which seems made for a relaxing picnic.
Buon appetito (hypothetically)!