Central Italy

Rome first is generally better: it’s more overwhelming, so doing it when you’re fresh helps. Three nights in Rome, then 4–5 nights in Florence, lets you return to manageable rhythms. Alternatively, if you’re combining Rome with the south (Naples, Pompeii), do Rome as your Rome + South anchor and leave Florence for a second trip. If you’re flying in and out of different cities, sequence based on your flights rather than the “right” order.

Book Colosseum and Vatican tickets online weeks in advance. Do the big museums (Vatican, Uffizi) on your most alert morning, not at the end of a travel day. Accept that you won’t see everything. In Rome, skip the smaller museums after the first two days and walk neighbourhoods instead (Trastevere, Campo de’ Fiori, the Ghetto). In Florence, one major museum per day is realistic; spend afternoons walking the surrounding hills or across the Ponte Vecchio into the Oltrarno. Hiring a private guide for the Vatican or Uffizi (half day, 150–200 euros) is often worth it: skip crowds, gain real knowledge.

For accessing small wineries and truly rural villages, yes, a car is valuable. For hill town bases (Siena, Montepulciano, Montalcino), you can arrive by train and explore the town and immediate surroundings on foot. Hire a car for 2–3 days to explore wine country, then drop it and base yourself in a town. The classic Chianti Classico road between Florence and Siena is best driven slowly and stopped on frequently; a hire car makes this possible. Taxis and local buses connect some towns, but a car offers freedom.

Montalcino is the gold standard: beautiful, manageable size, exceptional wine, and good restaurants without the Venice-level tourism. Pienza is smaller and even more theatrical, with stunning views across the Val d’Orcia. Greve in Chianti is larger and busier but excellent for wine access and central location. Montepulciano is dramatic (perched on a ridge) but steeper and more exhausting to walk. For a slower rhythm with fewer tourists, choose Montalcino or a smaller village nearby. Siena is busier and worth a day trip from any of these towns.

Skip the Cinque Terre (overcrowded, overpriced, overhyped). Skip day-tripping from Florence to Venice (it’s too far and feels rushed). Skip trying to do Rome, Florence, Siena, Perugia, and Assisi in two weeks (you’ll spend more time travelling than experiencing). Skip museums beyond two or three majors; you’ll retain more from walking and eating. Skip the obvious tourist restaurants in city centres; eat where locals eat, often a few blocks away.

Rome (3 nights), then either continue to Naples (3 nights as a coastal anchor) or move directly to Campania countryside. Naples is underrated: gritty, authentic food, and the gateway to Pompeii and Herculaneum (half-day trips). Alternatively, do Rome as a self-contained 4-night trip, then fly or take a train to Naples for the south. Mixing Rome with southern travel requires realistic expectations about how much ground you can cover without the trip feeling like constant transport.

Rome and Florence are absolutely possible with children, but modify the itinerary. Skip major museums and spend time in parks, fountains, and on the Tiber. Hire a stroller and accept slow mornings and early dinners. Hill towns are actually ideal with children: smaller scale, friendly locals, and outdoor meals. Tuscany countryside is more family-friendly than city centres. Avoid August (heat and crowds), and plan one family-oriented activity per day rather than marathon sightseeing.

April–May: mild weather, reliable sunshine, manageable crowds, spring gardens in bloom. September–October: golden light, warm afternoons, thinning crowds, harvest energy in wine country. Absolutely avoid August in cities (heat and closures); December is beautiful but with limited daylight. Winter (January–March) is quietest and moodiest; acceptable if you’re flexible about weather and enjoy empty streets.