citytripo

Italy

Italy in 14 days

14 days through Milan, Venice, Florence, Rome, and Naples. Each city follows its own plan from the stop base, and the trains in between are counted.

  • 5 cities
  • 64 stops
  • 6 h 35 by train
  • €1,220 to €1,494 per person

Data checked on October 7, 2026

The route at a glance

  1. MilanDays 1 to 3
  2. 2 h 15
  3. VeniceDays 4 to 6
  4. 2 h
  5. FlorenceDays 7 to 9
  6. 1 h 25
  7. RomeDays 10 to 12
  8. 55 min
  9. NaplesDays 13 to 14

The order follows the rails. Milan and Venice sit in the north, Florence and Rome in the middle, and Naples at the far end, so the route never doubles back. Flying into Milan and out of Naples, or home from Rome, saves a return trip north. Venice is a short detour east of the main line, which is why it comes second.

Days 1 to 3

Milan

Milan is a working city with a compact historic core, and most first-time visits start at the Duomo and fan out on foot. The big draws are the cathedral roof, the Last Supper, the Sforza Castle and a handful of museums. Outside the centre, the canals of the Navigli and the glass towers of Porta Nuova give two very different evenings.

Free walking tour of Milan

  1. Day 1Brera and the fashion district · Duomo and the centre

    Open this day's route in Google Maps

  2. Day 2Magenta and Sant'Ambrogio · Duomo and the centre

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  3. Day 3Porta Nuova and Monumentale · Castello and Sempione

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The full 3-day plan for Milan

Milan to Venice: 2 h 15 by train

Milano Centrale to Venezia Santa Lucia · Trenitalia, Italo

Take a train early in the morning or the evening before, so the day in Venice starts on time.

Days 4 to 6

Venice

Venice has no cars, so every visit happens on foot or by vaporetto. The big sights cluster around St Mark's Square at the east end, while Dorsoduro, San Polo and Cannaregio fill the west and north with museums, churches and quieter streets. Lanes are narrow and every canal means a bridge, so distances feel longer than they look on a map.

  1. Day 4St Mark's Square · San Polo

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  2. Day 5Dorsoduro · Grand Canal

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  3. Day 6Rialto · St Mark's Square

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The full 3-day plan for Venice

Venice to Florence: 2 h by train

Venezia Santa Lucia to Firenze Santa Maria Novella · Trenitalia, Italo

Take a train early in the morning or the evening before, so the day in Florence starts on time.

Days 7 to 9

Florence

Florence keeps most of its big sights inside a few square kilometres on the north bank of the Arno. The museums use timed tickets and close on set days, so the planning matters more than the walking. The Oltrarno side across the river is quieter and suits an afternoon.

Free walking tour of Florence

  1. Day 7Oltrarno · Signoria and the river

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  2. Day 8Signoria and the river · Santa Croce

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  3. Day 9Duomo and San Lorenzo · Santa Maria Novella

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The full 3-day plan for Florence

Florence to Rome: 1 h 25 by train

Firenze Santa Maria Novella to Roma Termini · Trenitalia, Italo

Take a train early in the morning or the evening before, so the day in Rome starts on time.

Days 10 to 12

Rome

Rome keeps its ancient core, the Vatican and its Baroque squares in separate districts, linked by long walks and short metro or bus rides. Most visits are built around two or three booked entries, with wandering and meals in between.

Free walking tour of Rome

  1. Day 10Ancient Rome and Capitoline Hill · Trastevere and Janiculum

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  2. Day 11Historic centre · Ancient Rome and Capitoline Hill

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  3. Day 12Vatican and Borgo · Historic centre

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The full 3-day plan for Rome

Rome to Naples: 55 min by train

Roma Termini to Napoli Centrale · Trenitalia, Italo

Take a train early in the morning or the evening before, so the day in Naples starts on time.

Days 13 to 14

Naples

Naples packs Greek street grids, Bourbon palaces and a major collection of Roman finds into a tight, steep and noisy centre. The best of it is free and outdoors: the lanes of the old town, the squares and the seafront. The museums and the underground sites are where the booking happens.

Free walking tour of Naples

  1. Day 13Centro Storico · Museo, Sanità and Capodimonte

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  2. Day 14Centro Storico · Royal Naples and the port

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The full 2-day plan for Naples

What to book for the whole route

These stops on the route need a ticket bought ahead.

  • Milan

    Pinacoteca di Brera

    Reservations are required and are made on the official booking site or by phone. Book a day and a time slot, and book earlier for weekends and for the free first Sunday.

    See the guided visit

  • Milan

    Leonardo's Last Supper

    Reservation is compulsory for every ticket, including free ones and children. Tickets are released in quarterly batches, with extra tickets put on sale each Wednesday at noon for the following week. Check the official site first and book as soon as your dates are open.

    See the guided visit

  • Venice

    St Mark's Basilica

    Tickets are named from the moment you book, and you can only enter in the slot you chose, with five minutes of tolerance. Book on the official ticket site. A slot showing zero is sold out.

    See the guided visit

  • Florence

    Florence Cathedral and Dome

    Book a Dome time slot online before you go. The entry is fixed to the date and hour you choose and cannot be changed. Covered shoulders and knees are required inside.

    See tickets

  • Rome

    Colosseum

    Entry is by timed ticket. Book online on the official ticket site as soon as your dates open, usually about a month ahead, and earlier in busy months.

    See the guided visit

  • Rome

    Borghese Gallery

    Reservation is compulsory and entry is by timed slot. Book as early as you can, since slots sell out.

    See the guided visit

  • Naples

    Sansevero Chapel Museum

    Every visit must be reserved in advance. Online tickets go on sale about two months ahead, with more released two days before, so check again if your date shows full. Online purchases cannot be changed or refunded.

    See the guided visit

What the route costs

Per person: tickets for the stops on the route, food and local transport. Trains between cities and the hotel are not included.

CityDaysTicketsTickets, food and transport
Milan 3 €89 €237 to €303
Venice 3 €97 €298 to €375
Florence 3 €147.50 €322 to €361
Rome 3 €115.50 €237 to €287
Naples 2 €62 €126 to €168

Stops with a ticket whose price we could not confirm are left out of the sum.

Trains between the cities

Frecciarossa and Italo run the fast services between these cities, and every seat on them is reserved when you buy. Regional trains are cheaper and slower, with no reserved seats, and a paper ticket has to be validated before boarding. Fast tickets go on sale months ahead and the cheapest fares sell out first, so book once your dates are fixed. Check the departure station on your ticket, since big cities have more than one.

When to go

April to June and September to October give mild weather and thinner crowds in all five cities. July and August are hot, especially in Rome, Florence and Naples, and winter is cold in the north with short days.

Before you go

  • Book the Last Supper in Milan, the Uffizi and Accademia in Florence, and the Colosseum and Vatican Museums in Rome before you buy the trains, since their timed slots set your dates.
  • Pack one bag you can carry up station stairs and over Venetian bridges, because lifts are rare and porters are scarce.
  • Many museums close one day a week, often Monday, so plan travel days for the day a city's main sights are shut.
  • Keep your phone charged and your ticket saved offline, as station Wi-Fi is unreliable and conductors check tickets on board.

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