Siena or Assisi

Siena & take the bus, not the train. The bus drops you off in the center of tow & the train station is nearly a mile out of town.

Have done both. Our choice would be Assisi although you wouldn't get as many tourist hours there as you would in Siena. For Siena, it's just over an hour on the SITA Corse Rapide bus (express). Lot's of time to rome around. In fact, you can even jump over to nearby San Gimignano on the bus. For Assisi, it's a 2.5hr trip to the Assisi train station which is not in Assisi. You need to take the bus to the hilltown. Simply go next door to the small shop adjoining the train station and buy tickets on the Line C bus. It stops right outside the shop. Take the bus all the way to the top of the town and walk down the steep hills. The Basilica is at the bottom. You can get off there first if you want but you walk up the hills to see the rest of the town. We just loved Assisi.

I've been to both. I would choose Siena in your situation because it's quicker to get to. They're both great.

I've been to both and would choose Assisi. Didn't like Siena, loved Assisi. It's much more charming and enjoyable imo.

Another vote for Assisi. It's probably my favorite Italian hill town, and to be honest, I wasn't overly impressed by Siena. Assisi just feels so much more medieval and cultural to me, whereas I get more of a college town feel out of Siena. In Assisi I can shop in the bottegas, while in Siena I can shop in the United Colors of Benetton. I've stayed in both, but I always go back to Assisi when I'm in Italy.

I see you have an even number of votes for each city!! It's like asking whether you should have apples or oranges, is the problem. We liked Assisi more than Siena (and I happen to like oranges more than apples!) It's a less touristy town, easy to get around, RS does a great job of explaining things.