I've noticed in Venice, Rome, and Florence that the traditional economy is being pushed out by the playground economy that comes with modern affluence. In old, historic city centers, as rents go up, longtime residents and families are pushed out. Recently, the Florentine government ended rent control and rental costs immediately spiked, driving artisans and shops catering to locals out of business -- to be replaced by boutiques and trendy places to eat and drink.
In both Florence and Rome, if you cross the river (into neighborhoods that are the European equivalent of "the wrong side of the tracks") you're more likely to find small family businesses eking out an existence for another generation -- like this cobbler's shop.
When exploring Florence, remember to take a moment to look above the trays of neon-colored gelato and enjoy the cityscape. This is a city of noble and elegant facades.
You can diligently visit all the museums and eat at all the right restaurants, but if you don't take a simply aimless stroll for a half-hour before crawling into bed, you're missing an important dimension of a great city. After dark, thoughtful floodlighting, reflections on cobbles, lonely street musicians, and local lovers all bring charm to streets that are otherwise teeming with traffic and workaday crowds.
I don't build my itineraries around festivals. But I'm constantly happening upon fun events filling the streets and squares. Standard operating procedure for any good traveler: when checking into your hotel, be sure to ask, "What's happening tonight?" I imagine half the tourists in Florence were in their hotel rooms on the last night of April when the streets were jammed for White Night Florence -- a nightlong celebration of Florentine good living when venerable facades became just backdrops to free concerts, dancing, dining, and street performances.
Lorenzo the Magnificent is just one of the many busts that greet visitors entering Florence's Uffizi Gallery, home to the best collection of paintings in Italy. Lorenzo must have been a big personality with Mick Jagger-sized energy and charisma.
While Lorenzo had nice hair and chiseled features, others in the family were not quite so well assembled. When you study how inbred Europe's aristocratic elites became over the ages, you stumble upon some of the physical downsides of tight families. This Medici, like many of Europe's royals, had a pretty distracting underbite.