41.90°N 12.50°EItaly
14days

Italy itinerary

2-Week Italy Itinerary

Two weeks lets you cover Italy's headline cities plus a slower countryside stretch through Tuscany — this route runs south to north, ending in Milan for an easy flight home.

Best monthsAprilMaySeptemberOctober

This route runs north from Rome, spending real time in each place rather than collecting cities. It ends in Milan, which has the best international flight connections for departure.

Days 1–3: Rome

Cover ancient Rome (Colosseum, Forum, Palatine Hill), Vatican City (Museums, Sistine Chapel, St. Peter’s), and the historic center (Pantheon, Trevi Fountain, Trastevere). See the 3-day Rome itinerary for a fuller day-by-day breakdown.

Days 4–5: Florence

Take the train to Florence (1.5 hours). Spend day four on the Uffizi Gallery and the Duomo, climbing the dome or Giotto’s Campanile for the skyline view. Day five: the Accademia (Michelangelo’s David) in the morning, then cross the Ponte Vecchio to the Oltrarno district for a quieter afternoon.

Days 6–7: Tuscan countryside

Pick up a rental car and head into the hills. Base yourself near Siena or in the Chianti region — spend one day in Siena itself (the Piazza del Campo, the striped cathedral) and one day driving between San Gimignano’s medieval towers and a vineyard or two for wine tasting.

Days 8–9: Cinque Terre

Drop the car in La Spezia and take the local train into the five villages — Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore. Two days is enough to hike the coastal trails between villages (check trail conditions ahead — sections close periodically) and still have time to swim.

Days 10–11: Venice

Train to Venice (via a connection). No cars here — everything moves by foot or boat. Day ten: St. Mark’s Square, the Basilica, and the Doge’s Palace, followed by a sunset gondola or vaporetto ride. Day eleven: get lost in the quieter Dorsoduro and Cannaregio neighborhoods, away from the cruise-ship crowds around St. Mark’s.

Days 12–14: Milan and Lake Como

Finish in Milan (2.5 hours by train from Venice). Spend a day on the Duomo, the Galleria Vittorio Emanuele II, and, if you book ahead (it sells out weeks in advance), Leonardo’s Last Supper. Take a day trip to Lake Como for a slower final stop before flying out of Milan Malpensa.

Practical tips

Book high-speed train tickets a few days ahead for better prices, and reserve the Uffizi, Accademia, and Last Supper well in advance — all three regularly sell out same-day slots in peak season.

Frequently Asked Questions

Is 2 weeks enough to see Italy?

It's enough to properly see six regions — Rome, Florence, Tuscany, the Cinque Terre, Venice, and Milan — without a rushed one-night-per-city pace. It's not enough to add the Amalfi Coast, Sicily, or Puglia too; pick one region to add if you have extra days, rather than stretching this route thinner.

Should I rent a car in Italy?

Only for the Tuscany leg. Trains cover Rome–Florence–Venice–Milan quickly and comfortably, and driving in city centers (Florence, Venice, Rome) is genuinely difficult due to restricted traffic zones (ZTLs) that fine tourists automatically. Rent a car for the countryside days only, then return it before Cinque Terre or Venice.

How do I get between cities?

High-speed trains (Frecciarossa or Italo) connect Rome, Florence, Venice, and Milan in 1.5–3 hours each, and are the easiest way to move between them. Book a few days ahead for better fares. The Cinque Terre has its own local train line connecting all five villages.

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