Florence

We stayed at Firenze No. 9, a modern-ish hotel about a 5 minute walk from the train station. Everyone there - particularly the dining room staff at breakfast - were incredibly friendly and fawned all over FDR, which was great. They upgraded us to a junior suite, so we had extra space to put the hotel crib. I'm not sure I would stay there again though; the lighting controls were extraordinarily complicated and made a Law & Order-style "ker-chunk!" every time you turned them on or off. Not ideal when you're trying to keep a baby asleep.

Since he's only 5 months old, he's still exclusively on formula, so that's all we had to pack in terms of his food. For a three day trip we just packed a tupperware full of formula and the little three-section food dispenser. Also, when he's asleep, he is ASLEEP. So at dinner, we could feed him his bottle at 8:30pm (7:30pm London time), put him in the cot in the stroller (this is where the Bugaboo shines), head out from the hotel at 9 and sit down to dinner around 9:30pm, and (fortunately) he stayed asleep during dinner. Risky strategy perhaps but sure beats a 7:30pm dinner and retreat to the hotel, or boring old room service.

During the days, we walked around Florence, which is a beautiful, relatively compact city to walk around with a baby in a stroller. Italians love babies, and if he got fussy during lunch time, one (or more) of the servers would come over and coo at him and just generally distract him. Grazi!

You don't need me to tell you what the tourist sights are - The Uffizi, The Duomo, The David (the real one and the copy), and the Ponte Vecchio - all are well navigable with a stroller though I imagine during peak tourist season, the crowds might make that more challenging. Another stroller-friendly activity is just puttering around an outdoor market (in our case, Santo Spirito, though there are many others).

Good luck finding a bathroom outside your hotel suitable for changing a baby. Plan on doing that in the stroller and/or "around a corner" somewhere. Hand sanitzer is key!

Plan the train journey back to Pisa better than we did. We were bad parents again, and after making a dash for a 10am train, we ended up having to sit on folding seats between carriages, with our monstrous pile of luggage, and FDR on our laps. That was harrowing, and I'm not sure we would have emerged unscathed but for the help of Italians who love babies (all of them).