Spello

We spent 5 nights in Spello in April 2019 and LOVED it. It's a beautiful little town and we rented a lovely apartment through VRBO. We didn't find English to be an issue - in the restaurants the servers had enough English plus our tortured Italian to be understood. In the little shops, English was a bit more of an issue, but it makes it more interesting and we really didn't have a problem being understood. You definitely should check further into the transportation issue - we had a car and found it to be very helpful in getting to the nearby small villages including Todi (we used Google Maps and had no issues). We thought Spello was much more charming than Assisi or the other large towns. Whatever you decide, I think you'll love Umbria - it's beautiful, great food and not nearly as crowded as Tuscany.

I did a day trip to Spello from Assisi two years ago, and recall the train trip taking only about 10 minutes! (Take a look at trenitalia.com for train schedules.) The train station in Spello is an easy 10 minute walk (at most) up to the city gate into the old, medieval town, though you'll need to take a bus or taxi from the old city of Assisi down (about 2 miles) to the Assisi train station in the flat valley (your hotel folks can help you out with those arrangements). If you don't want to deal with packing up and moving from hotel to hotel, you might consider just doing a day trip to Spello; it's really quite a small town, compared to Assisi. I also don't recall having much problem communicating; I try to speak some basic "traveler" phrases in Italian, but found that the kind people in shops and restaurants throughout Tuscany and Umbria generally spoke much more English than I did Italian. From Assisi you can also take the train to Cortona and Spoleto, among other lovely towns that might make other great day trips.

The bus to Spello from Assisi is much better than the train, because it leaves from the center of town (on each end) rather than the train station. There's no need for a bus office in Spello. I'm guessing we bought our bus tickets on the bus, though I frankly can't remember. But I know we never tried to find a bus office. We like both Assisi and Spello, but the fact that the Assisi train station is so far from the center of town is a point in its disfavor. Spello's train station is much closer to town.

I would not stay in both Assisi and Spello as they are very close together. We are staying in Assisi because I thought there was more to see and I wanted more than a day trip. I think it depends what your goals are. I thought being in Assisi early and late was an advantage to staying there. I think Spello is easier to day trip out of if you want to do much of that. And I think it is less crowded than Assisi.