The Italy multi-city planner that picks the right 3 cities
Italy trips fail when travelers try to do Rome + Florence + Venice + Cinque Terre + Amalfi + Sicily in 10 days. That's 6 regions and 5 train/plane connections, which is too many. The best Italy itinerary picks one big city (Rome), one art city (Florence), and one scenic third (Venice or Cinque Terre or Amalfi — pick one). The rest is pacing: 3 full days in each for first-timers, 4 in Rome if you want Vatican + ancient + one neighborhood done well.
The 10-day Italy classic (Rome 4 / Florence 3 / Venice 3)
Day 1 arrive FCO, Leonardo Express to Termini ($16), hotel in centro storico or Monti. Day 2 Colosseum + Palatine + Roman Forum (skip-the-line combo ticket $28/pp, book 45 days ahead). Day 3 Vatican Museums + Sistine + St Peter's (skip-the-line $37/pp, book 60 days ahead, start 8am before crowds). Day 4 Trastevere neighborhood + Villa Borghese + Piazza Navona at sunset. Day 5 high-speed train Rome→Florence 1h35m ($35–$65 book 90 days ahead on Trenitalia). Day 6 Uffizi Gallery ($30/pp, 60 days ahead) + Ponte Vecchio + Oltrarno neighborhood. Day 7 day trip to Siena + San Gimignano ($80 tour or drive rental $75 + tolls) or stay in Florence for Bargello + Accademia (David, $26/pp, 30 days ahead). Day 8 train Florence→Venice 2h05m ($30–$55). Day 9 St Mark's Basilica + Doge's Palace combo ($30/pp) + Rialto market morning + gondola sunset ($95 for 35 min for 2–6 people). Day 10 fly VCE home. Total for two: $5,400–$7,600 all in from U.S.
The 14-day Italy deeper trip
Rome 4 / Florence 3 / Cinque Terre 3 / Venice 3 / Milan 1. Add Cinque Terre between Florence and Venice. Train Florence→La Spezia→Monterosso 2h20m $35. Stay 2 nights in Monterosso (most accessible of the 5 villages), hike the Sentiero Azzurro between villages (currently closed between some villages due to landslides — check before going, $8/day Cinque Terre card). Train Monterosso→Venice 4h30m $40. Alternative 14-day: Rome 4 / Florence 3 / Amalfi 4 / Naples 2 / Rome 1. Amalfi is southern, more scenic, more driving required (rent SUV in Sorrento $85/day for 3 days, drive the coast). Total for two 14 days: $7,200–$10,400.
The 7-day Italy quick trip (Rome + Florence only)
4 Rome / 3 Florence. Skip Venice — it needs 3 days minimum to justify the train time. Or 4 Florence / 3 Rome inverted if you care more about art. Flights $650–$1,100. Total for two: $3,800–$5,400.
Rome: hotels by neighborhood
Centro Storico (walking to everything, expensive) — Hotel Nazionale $260/night, J.K. Place Roma $680/night. Monti (hip, walkable to Colosseum, cheaper) — Residenza Maritti $180/night. Trastevere (neighborhood vibe, 15 min walk across river) — Hotel Santa Maria $280/night. Avoid: Termini area (train station, sketchy at night, tourist traps) unless you have an early train. Avoid Airbnb in historic center — noise, stairs, no elevator is common.
Florence: hotels by neighborhood
Centro (Duomo area, walk to everything) — Hotel Davanzati $210/night, Portrait Firenze $780/night. Oltrarno (across river, authentic, quieter) — Hotel Lungarno $420/night. San Lorenzo (mercato area, cheaper) — Hotel Europa $160/night. Florence is small — walking across the entire centro takes 20 min, so location matters less than in Rome.
Venice: where to stay (or don't)
Stay on the main island (not Mestre on the mainland, which is 15 min train but loses the atmosphere). San Marco: central, crowded, expensive — Gritti Palace $1,100/night, Ca' Sagredo $620/night. Cannaregio: less touristy, where locals live, cheaper — Ca' Maria Adele $380/night, Hotel Ai Reali $420/night. Dorsoduro: art museums + youthful energy — Ca Maria Adele $380. Book 3+ months ahead for Carnival (February/early March) or mid-summer.
Train travel in Italy
Trenitalia high-speed (Frecciarossa, Frecciargento) — book 90 days out for €19–€29 "Economy" fares; walk-up is €60–€90. Italo is a competitor, often cheaper, comparable quality — book on italotreno.it. Regional trains (slower, between smaller towns) — buy at station, no reservation needed, €5–€15. Validate paper tickets in the yellow machines before boarding (skip if you bought e-ticket on app). First-class is worth $15 extra on Rome-Florence for wider seats and free coffee.
Food rules (that locals actually follow)
Cappuccino is a morning drink — ordering one after noon marks you as a tourist (nobody cares but baristas might smirk). Italian lunch is 1–3pm, restaurants close 3–7pm (aperitivo), dinner starts 7:30–8pm minimum, 8:30–10pm is prime time. Coperto (bread/cover charge €2–€5/person) is standard and mandatory. Tipping 5–10% rounded up is generous, not required. Tourist trap signals: menus in 6 languages, photos of food, a guy outside trying to usher you in. Good signal: no menu outside, Italian-only, locals at half the tables. Must-eats by city: Rome — cacio e pepe, carbonara, saltimbocca. Florence — bistecca alla fiorentina ($70–$120 for 2). Venice — cicchetti (small plates) at bacari bars, seafood risotto. Cinque Terre — anchovies (acciughe), trofie al pesto.
When to go
Peak (June–August): 90°F, crowded, 40–55% hotel premium, many restaurants shut in mid-August (Ferragosto). Shoulder (April–May, September–early October): 22°C, uncrowded, everything open — the best time. Off-season (November–March except Christmas): cold, some restaurants/hotels closed in coastal areas, but Rome and Florence run year-round with 35–50% hotel discounts. My pick: late April or late September.
FAQ on Italy trips
Can I drive in Italy? Useful in Tuscany, Umbria, Puglia, Amalfi. Avoid in Rome, Florence, Venice — cities are "ZTL" (zona traffico limitato) with €100 fines for driving through without permit. Rental: $45–$85/day manual, $65–$120 automatic (less common). Italian driving license? U.S. license + International Driving Permit ($20 at AAA) required. Italian currency? Euro (€). Cards accepted almost everywhere; keep €50–€100 cash for small cafes and coperto. Italian tipping? 5–10% for good service, round up for casual. Never tip 20% U.S.-style — it's weird, not generous. Italy with kids? Easy — Italians love kids, restaurants welcome them late, pizza and pasta bases cover picky eaters. Strollers struggle on cobblestones. Airbnb vs hotel? Hotel for 1–3 nights (consistency). Airbnb for 4+ (kitchen + laundry). Central Rome Airbnbs often have no elevator and 3-flight climbs. Is Rome safe? Yes, mostly. Pickpockets on metro and around Termini, Colosseum, Vatican. Keep wallet in front pocket, phone in zipped bag. Cinque Terre worth it? Yes for a 2-night stop. Don't day-trip from Florence — it's 2h20m each way. Rome or Florence first? Rome first (bigger, wilder — easier to land and adjust). Florence after (calmer, walkable, fewer scams).
Related tools
Plan with European itinerary planner, pack with Europe packing list, convert euros via currency calculator, and use jet lag estimator.