Deciding to stay either 2 or 3 nights in Assisi?

Have a taxi take you up to the Eremo of St. Francis, the hermitage with woodlands and walking paths surrounding it above the city of Assisi. Beautiful place.

I was only there for a day and a half. I enjoyed the RS self-guided walk. Il Foro Romano is a very well done museum showcasing the ancient Roman ruins. There are lots of shops that will entice you in and almost every turn brings either a charming street, an interesting medieval building or a beautiful view.

Two nights is probably enough unless you're planning to visit nearby towns or sights. That said, if you have an extra night in your itinerary, Assisi is a great place to slow down for a couple of days in the middle of a busy vacation. When in Assisi, I enjoy eating at Trattoria Pallotta down a narrow street off the main square. It's family run and serves traditional local dishes at good prices.

I love Assisi. The second time I went (in 2015) it was to spend two weeks taking a language class. You won't find restaurants that aren't also visited by tourists, given the town's economy.

That said, here's a really good thread for you to check out (Look for my response about five posts down):
https://community.ricksteves.com/travel-forum/italy/local-not-touristy-restaurants-in-assisi-and-siena-italy-6debb074-ae1e-43e5-92e6-1fefc53bb060

I'm in Assisi for 2 weeks every year - I'm a director of the music festival Assisi Performing Arts. This will be year 16 and I still find places to discover, scenery that rejuvenates, people who are glad to see me, food that . . . ok, you get the point: I love being in Assisi. Night time is so very different than day time in Assisi. The tourist groups are gone. The serenity returns. I like all the ideas I've heard in this conversation. Can I add a few: La Lanterna is wonderful. From the Piazza Commune head up the mountain towards San Rufino. You'll see the lanterns (Lanterna) on your left. My favorite (many of us from the festival plan our 'special' lunch here) is La Fontanella. From the Piazza Commune head down towards the Basilica San Francesco. When you get to the toy store with all the Pinocchios, turn left. When the walkway ends, turn left again. La Fontanella will be on your right within a very few steps. Franca is a wonderful hostess and chef. We like to give her a couple of days notice and tell her how much we want to spend per person (20-25 euro per person) and leave it up to her. Sit in the garden for a spectacular view of the valley. The food is all organic and she shops every morning for the freshest ingredients. Hmm, I'm getting hungry.

Want more (hey, it's a walking city so you don't have to count calories!)? La Terrazza di Properzio, on Via Metastastio. From Piazza Commune go up the street (here the street name is Via San Paolo) to the left of the church Santa Maria Sopra Minerva - and keep walking. It will be on your left. It's a bit of a walk which is good - you'll be really hungry and happy to be fed!

For the best lunch (or afternoon snack), I like going to any of the shops that have a wild boar on the counter. Let them make you a sandwich, open your bottle of wine and just sit on the Piazza Commune to people watch. Remember: you deserve this!

Assisi is a great walking city. We joke that it is uphill in both directions - and I can prove it. This is one of those places where getting lost will give you plenty of fond memories. This is a VERY safe place to wander, even at night alone. There are several artist studios in the city for art lovers. The local wines are cheap and very, very good. And, of course, there is gelato! So many flavors, so little time. I believe that all the places I have mentioned will show up on a Google map, and certainly in TripAdvisor. Sigh, can't wait to get back to Assisi!

Lots of great ideas...keep them coming!