Italy is less a country to see than one to taste, slowly, over a long lunch that turns into a long afternoon. It has more art, history, and coastline than seems fair for one nation, and the only real mistake is trying to fit too much of it into too little time.
Italy layers its pleasures. There is the art and architecture, centuries of it, in cities that are open-air museums. There is the food, which changes from region to region and is taken seriously everywhere. And there is the coastline, from dramatic cliffs to quiet fishing villages. Few places reward unhurried travel so generously.
Rome for ancient ruins and timeless streets. Florence for Renaissance art and Tuscan light. Venice for canals at dawn before the crowds. The Amalfi Coast for cliffside villages and lemon groves above the sea. Tuscany and Umbria for hill towns, vineyards, and the long Italian lunch done properly.
April to June and September to October offer warm weather without the peak summer crush. July and August are hot and busy, especially on the coast, so plan around the heat if you travel then.
Eat where the menu is written by hand and changes often. The simplest places, away from the main squares, almost always serve the best food at the fairest prices.