Arcway
Italy in 3 weeks: a north-to-south itinerary from Milan to Sicily by train and ferry

Italy in 3 weeks: a north-to-south itinerary from Milan to Sicily by train and ferry

Sat 5 – Sat 26 Sept 2026·22 days·Milan · Florence · Pienza · Rome · Naples · Positano · Palermo · Taormina
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Times are local to each place

22 days · Milan · Florence · Pienza · Rome · Naples · Positano · Palermo · Taormina · Best in September

Three weeks is enough to see Italy from the Alps to Sicily without spending every other day packing. This 22-day itinerary starts in Milan and works its way south through Florence, the Val d'Orcia, Rome, Naples, the Amalfi Coast and Palermo, ending in Taormina below Mount Etna. Most of the travel is by train, bus and ferry, with two short car rentals where public transport gets awkward: the Tuscan countryside and the drive across Sicily.

It's built around September, when the crowds of high summer thin out but the sea is still warm and the Amalfi Coast ferries are still running.

What you're looking at: this is a real Arcway trip. The map and the day-by-day timeline below come from the trip's bookings: flights, trains, buses, ferries, stays and activities, each in local time. The times are an example. Check current timetables and opening hours before you book anything.

At a glance

  • 22 days, 8 bases: Milan (3 nights), Florence (3), a farm stay near Pienza (3), Rome (3), Naples (2), Positano (2), an overnight ferry, Palermo (2) and Taormina (2).
  • Getting around: 2 flights (in to Milan Linate, out from Catania), 2 high-speed trains, 2 buses, 3 ferries (including an overnight crossing from Naples to Palermo) and 2 car rentals.
  • Pace: one or two planned things a day, with free days in Milan and Rome.

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Saturday · 5 SeptemberDay 1
BusLinate Shuttle · Linate Shuttle
10:45Milano Linate Airport
25m
11:10Milano Centrale
Booking.com
Stay · Check-in 15:00

Casa Brera

Via Fiori Chiari 12, 20121 Milano
Check-outTue 8 Sept · 11:00
Nights3
RoomDeluxe double with balcony
Activity · 18:30

Duomo rooftop at sunset

Duomo di Milano, Piazza del Duomo, 20122 Milano
Sunday · 6 SeptemberDay 2
Activity · 10:15

The Last Supper

Santa Maria delle Grazie, Piazza di Santa Maria delle Grazie 2, 20123 Milano
Activity · 20:00

An evening at La Scala

Teatro alla Scala, Via Filodrammatici 2, 20121 Milano
Monday · 7 SeptemberDay 3
No bookings. A free day in Milan.
Tuesday · 8 SeptemberDay 4
11:00Check out of Casa Brera
Airbnb
Stay · Check-in 15:00

Terrace apartment in Oltrarno

Via Maggio 28, 50125 Firenze
Check-outFri 11 Sept · 10:00
Nights3
Wednesday · 9 SeptemberDay 5
Activity · 09:15

Uffizi Gallery, timed entry

Galleria degli Uffizi, Piazzale degli Uffizi 6, 50122 Firenze
Activity · 17:00

Pasta-making class

Cucina di Nonna Lucia, Via Romana 41, 50125 Firenze
Thursday · 10 SeptemberDay 6
Activity · 18:45

Sunset at Piazzale Michelangelo

Piazzale Michelangelo, Piazzale Michelangelo, 50125 Firenze
Friday · 11 SeptemberDay 7
10:00Check out of Terrace apartment in Oltrarno
Car rental · Pick-up 10:30

Europcar · Fiat 500 Cabrio

Europcar Firenze Borgo Ognissanti
Agriturismo Poggio ai Cipressi
Stay · Check-in 16:00

Agriturismo Poggio ai Cipressi

Podere Poggio ai Cipressi, 53026 Pienza SI
Check-outMon 14 Sept · 08:30
Nights3
RoomDouble room, valley view, breakfast included
Saturday · 12 SeptemberDay 8
Activity · 09:30

Vespa tour of the Val d'Orcia

Piazza Dante Alighieri, Pienza, Piazza Dante Alighieri, 53026 Pienza SI
Sunday · 13 SeptemberDay 9
Activity · 16:00

Wine tasting in Montepulciano

Cantina del Colle, Via di Gracciano nel Corso 82, 53045 Montepulciano SI
Monday · 14 SeptemberDay 10
08:30Check out of Agriturismo Poggio ai Cipressi
10:00Return car at Europcar Siena
Booking.com
Stay · Check-in 15:00

Albergo del Cedro

Vicolo del Cedro 9, 00153 Roma
Check-outThu 17 Sept · 11:00
Nights3
RoomSuperior double, courtyard side
Activity · 18:30

Trastevere food tour

Piazza Trilussa, Piazza Trilussa, 00153 Roma
Tuesday · 15 SeptemberDay 11
Activity · 09:00

Colosseum underground and arena tour

Colosseum, Piazza del Colosseo 1, 00184 Roma
Wednesday · 16 SeptemberDay 12
Activity · 07:30

Vatican Museums, early entry

Vatican Museums, Viale Vaticano, 00165 Roma
Thursday · 17 SeptemberDay 13
11:00Check out of Albergo del Cedro
Booking.com
Stay · Check-in 14:30

B&B Spaccanapoli 23

Via San Biagio dei Librai 23, 80138 Napoli
Check-outSat 19 Sept · 10:00
Nights2
RoomDouble room with balcony
Activity · 18:00

Pizza-making class

Pizzeria Da Gennaro e Figli, Via dei Tribunali 94, 80138 Napoli
Friday · 18 SeptemberDay 14
Activity · 09:30

Pompeii with a guide

Pompeii Archaeological Park, Porta Marina, 80045 Pompei NA
Saturday · 19 SeptemberDay 15
10:00Check out of B&B Spaccanapoli 23
Casa Limoneto
Stay · Check-in 14:00

Casa Limoneto

Via Cristoforo Colombo 71, 84017 Positano SA
Check-outMon 21 Sept · 10:30
Nights2
RoomSea-view double with terrace, breakfast included
Sunday · 20 SeptemberDay 16
Activity · 08:00

Path of the Gods hike

Sentiero degli Dei, Piazza Paolo Capasso, 80051 Bomerano NA
Activity · 17:30

Sunset boat along the coast

Spiaggia Grande, Positano, Via Marina Grande, 84017 Positano SA
Monday · 21 SeptemberDay 17
10:30Check out of Casa Limoneto
Tuesday · 22 SeptemberDay 18
Airbnb
Stay · Check-in 12:00

Palazzo apartment in the Kalsa

Via Alloro 54, 90133 Palermo
Check-outThu 24 Sept · 09:30
Nights2
Activity · 17:30

Street-food tour of Ballarò and Capo

Mercato di Ballarò, Via Ballarò, 90134 Palermo
Wednesday · 23 SeptemberDay 19
Activity · 10:00

Monreale Cathedral

Monreale Cathedral, Piazza Guglielmo II 1, 90046 Monreale PA
Thursday · 24 SeptemberDay 20
09:30Check out of Palazzo apartment in the Kalsa
Activity · 12:30

Lunch and a swim in Cefalù

Cefalù beach, Lungomare Giuseppe Giardina, 90015 Cefalù PA
Booking.com
Stay · Check-in 18:00

Villa Ginestra

Via Bagnoli Croci 60, 98039 Taormina ME
Check-outSat 26 Sept · 10:30
Nights2
RoomDouble with sea view
Friday · 25 SeptemberDay 21
Activity · 05:00

Etna at sunrise by 4x4

Rifugio Sapienza, Piazzale Rifugio Sapienza, 95030 Nicolosi CT
Activity · 17:30

Greek theatre of Taormina

Ancient Theatre of Taormina, Via del Teatro Greco 1, 98039 Taormina ME
Saturday · 26 SeptemberDay 22
10:30Check out of Villa Ginestra
14:30Return car at Europcar Catania Airport
Home in AmsterdamSat 26 Sept · 20:15

Day by day

  1. Day 1 · Arrive in Milan

    Fly in to Linate, the airport closest to the city, and take the airport bus to Milano Centrale. After checking in around Brera, finish the day on the Duomo rooftop at sunset. Rooftop tickets are timed, so book a slot rather than queueing.

  2. Day 2 · The Last Supper and La Scala

    Leonardo's Last Supper at Santa Maria delle Grazie can only be seen with a booking, in 15-minute visits. The museum releases tickets roughly three months ahead, and asks you to be at the ticket office 30 minutes before your slot. It's closed on Mondays. In the evening there's a performance at Teatro alla Scala.

  3. Day 3 · A free day in Milan

    Nothing booked. Use it for the Brera Art Gallery, the Navigli canals or a slow morning.

  4. Day 4 · Train to Florence

    A Frecciarossa high-speed train covers Milan to Florence Santa Maria Novella in under two hours. Stay in the Oltrarno, the quieter artisans' district across the river.

  5. Day 5 · Uffizi and a pasta class

    Book a timed entry for the Uffizi to avoid the longest queues. In the afternoon there's a hands-on pasta-making class.

  6. Day 6 · Florence at your own pace

    A free day that ends at Piazzale Michelangelo for the sunset view over the city.

  7. Day 7 · Pick up a car and head into Tuscany

    Collect the rental car in central Florence and drive south to a farm stay near Pienza. Florence's historic centre is a camera-enforced limited traffic zone (ZTL), so ask the rental desk for the permitted route out before you set off.

  8. Day 8 · Val d'Orcia by Vespa

    A Vespa tour from Pienza through the cypress-lined hills of the Val d'Orcia.

  9. Day 9 · Montepulciano

    An afternoon wine tasting in Montepulciano, a short drive from Pienza.

  10. Day 10 · Bus to Rome

    Return the car in Siena and take a long-distance bus from Siena station to Roma Tiburtina. In the evening there's a food tour starting at Piazza Trilussa in Trastevere.

  11. Day 11 · Colosseum, underground and arena

    The underground levels and the arena floor need a specific ticket type, not the standard entry, so book the exact tour you want.

  12. Day 12 · Vatican Museums, early

    An early-entry slot at the Vatican Museums, before the main crowds arrive. The rest of the day is free.

  13. Day 13 · Train to Naples, then pizza

    A high-speed train from Roma Termini reaches Napoli Centrale in a little over an hour. Stay near Spaccanapoli in the historic centre, and make your own pizza at an evening class.

  14. Day 14 · Pompeii

    A guided visit to the Pompeii Archaeological Park. Bring water and sun protection: there's little shade on the site.

  15. Day 15 · Ferry to Positano

    Take the boat from Molo Beverello in Naples to Positano. The Naples–Positano ferries are seasonal: in 2026, NLG's sailings ran from 1 April to early November. Rough seas can cancel boats at short notice, so keep the land route via Sorrento and the coastal bus as a backup.

  16. Day 16 · Path of the Gods

    Start early for the Sentiero degli Dei, the cliff path between Bomerano (Agerola) and Nocelle above Positano, then end the day on a sunset boat along the coast.

  17. Day 17 · Back to Naples and the night ferry to Sicily

    An afternoon boat back to Naples, then an overnight ferry to Palermo with a cabin. You arrive early the next morning, which saves a hotel night and a travel day.

  18. Day 18 · Palermo street food

    Check in to an apartment in the Kalsa quarter, then take an evening street-food tour of the Ballarò and Capo markets.

  19. Day 19 · Monreale

    Monreale Cathedral and its gold mosaics sit in the hills just above Palermo. It's part of the UNESCO World Heritage site Arab-Norman Palermo and the Cathedral Churches of Cefalù and Monreale.

  20. Day 20 · Across Sicily via Cefalù

    Pick up a rental car in Palermo, stop in Cefalù for lunch and a swim, and continue to Taormina for the last two nights.

  21. Day 21 · Etna at sunrise, Taormina at sunset

    A very early 4x4 trip up Mount Etna from Rifugio Sapienza for the sunrise, then the ancient theatre of Taormina in the late afternoon.

  22. Day 22 · Fly home from Catania

    Return the car at Catania airport and fly home.

Questions

Is three weeks enough to see Italy from north to south?
Three weeks lets you cover Milan, Florence, Tuscany, Rome, Naples, the Amalfi Coast and Sicily with two to three nights in each place. That's enough to settle in rather than just pass through. With two weeks, you'd usually drop either Sicily or Tuscany.
Do I need a car for this itinerary?
Only for two short stretches: the Tuscan countryside around Pienza, and the drive across Sicily from Palermo to Taormina. Everything else is by train, bus and ferry.
When can you take the ferry from Naples to Positano?
The direct Naples–Positano boats are seasonal. In 2026, NLG's sailings ran from 1 April to early November. Outside that season, or when the sea is rough, take the train or bus to Sorrento and the coastal bus on to Positano.
How do I use this itinerary for my own trip?
Copy it into Arcway, which is free, and choose your dates. Arcway shifts every day to match and keeps all the times local. Copied items aren't booked, so Arcway flags the gaps you still need to fill: a night with nowhere to stay, or a leg with no transport. Then forward your own booking emails and they slot into the trip.
Copy this trip into Arcway

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