Wonderful Cities in Italy


Sun, fantastic nature, varied landscapes – all this and more, is Italy. The country in southern Europe has been one of the most popular destinations for years.

After all, there is a lot to discover, from mouthwatering homemade pasta to colorful seaside cities. On this Italy itinerary, we show you nine places you shouldn’t miss.


Where To Buy Tickets: OMIOTrenitalia

Countries Visited: Italy

Price Range: $$$

Recommended Days: 2-3 weeks

Riding Hours: Approx. 11 hrs

Distance: 854 km

Transportation: Train, Bus, Ferry

Venice ➝ BolognaFlorence ➝ PisaSiena ➝ RomeNaples ➝ Capri ➝ Positano

Venice: UNESCO World Heritage Site

In the northeast of Italy lies the floating city, which is at least one of the numerous nicknames of Venice. The city is located in a lagoon and is literally “built on the water”.

The history of today’s economic and tourism center goes back to the time of the Etruscans. Today, the Piazza di San Marco or one of the other 124 churches are especially worth seeing.

In addition, every visitor to Venice should take a gondola ride through the canals, besides on foot, it’s the best way to see the city.

Venezia San Lucia → Bologna Centrale | Duration: 1:27 | Transfers: 0


Traveling from Venice to Bologna is extremely easy and several connections are available throughout the day leaving Venezia San Lucia every 15-40 minutes. 

Bologna: The Educated, The Fat, And The Red

Bologna is located in the Italian region of Emilia-Romagna. The city’s roots date back to the 6th Century BC and in Italian has a nickname of La Dotta, La Grassa, and La Rossa which literally translates to “the educated, the fat, and the red.”

Besides the dramatic buildings such as the Basilica di Santo Stefano or the palaces along the Piazza Nettuno, one should pay attention to the museums of the city. The ones especially worth seeing are the Jewish Museum and the Museo della Storia di Bologna.

Bologna Centrale → Firenze S.M. Novella | Duration: 0:40 h | Transfers: 0


In less than one hour you can be in another famous Italian city. Connections from Bologna to Florence leave every 15 minutes throughout the day, leaving you plenty of time to soak up Bologna to catch the train to your next destination for the famous golden hour over the red rooftops.

Florence: A City Full Of Art History

A city primarily influenced by the powerful monarchal Medici family, and by cultural giants, Michelangelo and Da Vinci leave us now with its architectural and artistic highlights.

Florence can be easily explored on foot and with a walking tour, you can easily get the must-knows about the city.

The landmark of the city is the Cattedrale di Santa Maria del Fiore to get your bearings and before you leave, make sure to visit the Uffizi Museum and a walk across the oldest bridge in the city, Ponte Vecchio.

Firenze S.M. Novella → Pisa Centrale | Duration: 1:00 h | Transfers: 0


The next destination will take only an hour to reach with connections leaving Florence’s main train station every 30 minutes. 

Pisa: The Leaning Tower

The landmark of Pisa is the Torre pendente di Pisa and is better known as the “Leaning Tower of Pisa“.

But the city in Tuscany, not far from the river Arno, has much more culture to offer than a not so straight tower, such as the cathedral “Santa Maria Assunta.”

You can find the famous Pisan-Italian art exhibited in numerous museums in Pisa in the Museo Nazionale di San Matteo or the Museo dell’Opera del Duomo.

Pisa Centrale → Siena | Duration: 1:44 | Transfers: 1


The next destination takes less than two hours to reach. Take a train from Pisa Centrale to Empoli where connections leave every 20-30 minutes, there switch to a train to Siena where connections leave every 30-60 minutes.

Siena: Art, Culture, And History

The city situated in the renowned wine region of Tuscany is heaven on earth for the wine lovers out there. Siena is another Tuscan city yet different from the last as it protrudes a romanticism with its medieval buildings.

The Palazzo Pubblico is also worth seeing and in the square outside there are plentiful places to enjoy the large Piazza Del Campo, the grand public square. One enjoys the best view over Siena from its tower, the Torre del Mangia.

Siena → Roma Terms | Duration: 3:30 h | Transfers: 1


The next journey requires a transfer and a wait in Chiusi-Chianciano Terme. Take a train from Siena to Chiusi-Chianciano Terme which takes around 1:15-1:30h. These connections are every 30 minutes to 90 minutes depending on the time of day. From the transfer station, take a train to Roma Terms which takes around 1:39-2:15h. Connections to Rome leave every 0:45-2:00h.

Rome: The Eternal City

Rome, the capital of Italy, with over 2.8 million inhabitants, is the largest city in the country.

Due to its history and countless sights, Rome is also the Italian tourist magnet for good reasons.

Particularly worth seeing are the Vatican and the Vatican Museums. Furthermore, in the Roman Forum one walks on the traces of the early republic and enjoys an unforgettable view over the metropolis from the Castel San’Angelo.

Roma Termini → Napoli Centrale | Duration: 1:10 h | Transfers: 0


A well commuted route, this direct train takes a little over an hour to reach Naples and connections are available every 5-30 minutes from Rome’s main train station.

Naples: At The Foot of Vesuvius

Naples is the third-largest city in Italy. The megacity is located in the west of the “boot” and is the capital of Campania.

The metropolis is regarded as the place where pizza was invented. Its silhouette, for example, is marked by the three fortresses Castel dell’ Ovo, Castel Nuovo, and Castel Sant’Elmo.

Visitors to the city should not miss the Duomo San Gennaro, the Basilica di Santa Chiara or the Museo Nazionale di Capodimonte.

Porto di Napoli → Porto di Capri | Duration: 0:50 h | Transfers: 0


This next connection takes less than an hour and is by ferry. Connections leave every 1-3 hours depending on the time of day. The ferries leave hourly during the early morning.

Capri: The Pearl In The Gulf Of Naples

Very close to Naples lies the striking rock island of Capri. Its history goes back to the Palaeolithic era.

The highlight par excellence, which today attracts thousands of tourists to the island every year, is the Blue Grotto. In addition, Capri visitors can expect numerous caves, picturesque villages, and, for example, the sophisticated Marina Grande.

The most breathtaking view over the ten square kilometers of the island can be enjoyed from Monte Solaro, the largest mountain on the island of Capri.


Porto di Capri → Porto di Positano | Duration: 0:30 h | Transfer: 0


This connection is by a ferry operated by three different companies and with six connections to Positano daily.

Positano: Colorful City On The Amalfi Coast

On the south coast of the Sorrento peninsula, in the west of Italy, lies the small town of Positano. While the town on the Amalfi coast was a refuge for artists and writers from all over the world during WWII, today it is mainly tourists enjoying its beauty.

Especially worth seeing are the church Santa Maria Assunta together with the Black Madonna or the Grotta dell’Incanto. Also before wrapping up your Italy itinerary, one should not miss a day at the beach where Positano looks perfectly nestled into the mountainside.

If you would like to continue back to Rome it will take just over 3 hours, from which you can take a train in any direction or fly back home. To get to Rome, take a taxi to Meta or a bus from Positano Chiesa Nuova Bus Station to Meta (0:25h), from Meta you can take the train to Napoli P. Garibaldi train station (1:07h). There are connections every 25 minutes to Naples. Upon arriving at Napoli P. Garibaldi you will need to transfer to Napoli Centrale which is right next door. From Naples central station, connections are available every 5-30 minutes to Roma Termini (1:10h).

*Disclaimer: Due to the fluidity of transportation schedules, the information seen on RailwayHero may not be up to date at the time of readíng. Always double-check with the operator for the latest information.


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