17 Nights in Italy

Got back last week from a great trip to Italy with my wife, her mom (who hadn't been back in 50 years), and our two year old daughter. We flew into Milan for a jetlagged day and a half. We spent about 45 seconds of our alotted 15 minutes with the Last Supper (because the little one was getting rowdy), but I was very impressed even in the limited time. We enjoyed the parks, canal area, duomo, apertivo, and zipping around the manageable city on public transit.
We then trained to Levanto where we spent 3 nights enjoying the beach and lovely main square with great playground accompanied by aperitivo spots. The Cinque Terre Trains were a mess while we were there, causing us to abandon plans to visit one day (instead walking through the tunnels to Bonassola), but we did manage a quick morning stop in Vernazza the next day with a boat ride to Monterosso. Had a delicious burrata, truffle, prosciutto pizza at La Picea.
Trains were back to normal the day we left, so our quick lunch stop in Pisa was easy on the way to Florence for 3 nights. We had a giant (by our NYC standards) apartment near the Uffizi Gallery in Florence with wonderful Trattoria Roberto downstairs. I had time for a morning run over the hill to Bonassola for some probably not worth the squeeze views. Florence was beautiful (if crowded in spots) and had an amazing playground that included an indoor area with toys that we visited at least 3 times for the little one. We had an unexpected delicious shirmp and octopus taco(?!) lunch at Chiosco di Mare. Had a delightful family lunch at L'Arte di Dory in a more residential area where the resautrant had a play area and the owner brought toys to our table. And a delightful aperitivo along the banks of the Arno at the Cuban Themed (because why not?) outdoor cafe Habana 500. I had one morning run along the Arno into the south side of Florence and Piazza Michelangelo (for worth the squeeze views) along what turned out to be the route for a 10K race that was happening later that day.
We picked up a car (black hybrid Jeep Renegade that I enjoyed driving) at the Hertz near the train station and then headed towards our agriturismo near Assisi for 5 nights). On the way we had a delicious lunch at Ristorante La Terrassa in Monte San Savino (paccheri with eggplant and tomatoes was divine). The toddler didn't get enough nap time in the car so she was a bit fussy, but of course the owner and our waitress soothed and entertained her and gave her some chocolate egg candies. Our first full day we visited Assisi and then headed to a restaurant in Panicale (Lillo Tatini) that my wife and I had eaten at on our previous visit and had another delicious meal (good asparagus pasta and pork and duck and ricotta necci) with the atmosphere of the town square and post-lunch landscape views of Lake Trasimeno. On the way home we stopped in Deruta for some ceramic souvenirs. The next day we drove to Senigallia on the Adriatic Coast for a pleasant, if unremarkable, beach day. I woke up early the next day and ran up the hill to Assisi and then above Assisi (nice views). We drove to Gubbio, which was very pretty but the number of cars took some away from its charm. It had a large great playground right next to the roman theater that the little one enjoyed. On the way back we had a great lunch (decadent pistachio burrata and melt in your mouth strudel with prosciutto, sausage, and mozzarella) with great views in a garden at Taverna Dell'Orso in SantEgidio which was just a spot down some one-car-for-two-direction roads off the highway. Our final day we visited Spello and Bevagna before having an afternoon at the pool and pizza at home.

The next morning we stopped outside Todi before a scenic drive to Orvieto where we spent one delightful night and I ran the ramparts. We then trained to Rome and spent 3 nights absorbing the history (fantistic Museum at Palazzo Massimo) and atmosphere it is known for (and amazing eggplant pizza at TerraMia Pizzeria).