Florence

Florence is the most concentrated collection of great art and architecture on earth — a city of 370,000 that somehow houses the Uffizi, the Accademia (and Michelangelo's David), Brunelleschi's Duomo, the Ponte Vecchio and Giotto's Bell Tower within a 15-minute walk. The crowds in summer are real and relentless — book everything months ahead or arrive in October. The Oltrarno neighbourhood across the Arno river is the antidote: leather workshops, family trattorie, the Pitti Palace gardens, fewer tourists. Florentine food is the most uncompromising in Italy: bistecca Fiorentina (rare, thick, no sauce), ribollita bean soup, lampredotto tripe from a street cart. The wine is Chianti Classico. The gelato is a religious experience — Gelateria dei Neri or Sbrino will ruin everywhere else. October and November are ideal: harvest season, warm days, the crowds thinning, the light turning golden.