2 weeks in Italy (14 days) – LegendaryTrips Classic Itinerary

The perfect itinerary to experience La Dolce Vita

Italy is a beautiful all-round country that you could easily travel for months with the same enthusiasm. Beautiful landscapes, historically riched cities with architecture and art dating back to the Middle Ages and the Renaissance and, of course, delicious food and wines renowned around the world for their unique quality make Italy one of the most interesting destinations there is.

It was a tough debate and many espressos were consumed before reaching a consensus but here it is, at last: LegendaryTrips’ classic itinerary to spend the perfect 2 weeks in Italy!
This trip goes from Milan to Rome through Venice, Bologna, Florence and the Tuscan countryside. Hope you enjoy!

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Trip route

Step by step

Days 1-2: Milan

Start your 2 weeks in Italy with the economic capital, Milan. Some find Milan's business grit unappealing, yet it is what makes it the most dynamic city of Italy on all fronts. The city also certainly doesn't fall short when it comes to beautiful architecture, culture and culinary wonders.

If there are two things you should not miss in Milan these are the Milan Cathedral where you could climb the Duomo if you have time and Santa Maria delle Grazie where you can see Leonardo Da Vinci's Last Supper, perhaps the greatest Renaissance painting. It''s advised to book your tickets in advance.

Days 3-4: Venice

On the 3rd day take an early morning train to Venice (3-4 hours – tickets need to be pre-booked). After arriving head to Piazza San Marco (St. Mark's Square in English) where are located many shops and cafés but also Palazzo Ducale (Doge's Palace) and Basilica di San Marco (St. Mark's Basilica).

Any visit of Venice wouldn't be complete without a tour in gondola of the city and its beautiful canals and bridges (although it's certainly not a cheap activity!).
Your second day in Venice could be spent exploring the beautiful Grand Canal and, if you are into art, visiting Gallerie dell'Accademia where can be appreciated some of the most important Venetian paintings up to the 18th century and even the famous Vitruvian Man drawing by Leonardo Da Vinci.

Days 5-6: Bologna

After these two days in Venice, it's time to move on to the next destination of this trip itinerary: Bologna. This will take you only one and a half hour by train. Although it would be unfair to resume Bologna to its extraordinary food, it is what this city is the most famous for (have you heard of the bolognese sauce, actually referred to as 'al ragu' in Italy?).

Besides food that you should definitely take time to enjoy (how about a cooking class for lunch?), Bologna has also many interesting places to visit starting with the Basilica of Santo Stefano and Piazza Maggiore where is also located the Basilica of San Petronio.

Days 7-8: Florence

Two days is not a lot to fully enjoy Florence, especially if you are very into Renaissance but let's try to still make the best of it. Take a train from Bologna to Florence early in the morning. I see you starting to curse at this trip itinerary that don't let you sleep in the morning, but this time it will be a short ride (less than a hour).
Florence is quite compact so it's actually easy to see most sights within a day by walking (or by bus if you don't want to get tired). Wander around, sit at a terrasse and have a good coffee to get a first feel of the city. After that start a thorough tour and visit the places that interest you the most.

The best spots in our opinion are the following:
- Uffizi: a must-see for any Renaissance art lover; just Botticelli's paintings are worth the entry
- Catedral Santa Maria del Fiore (Florence Cathedral): make sure to climb the Duomo for a stunning view of the city and a close look at Vasari and Federic Zuccari's fresco
Basilica di San Miniato al Monte for its Romanesque architecture and perfect location on top of Florence – perhaps the most underrated sight the city has to offer.

Day 9: Chianti region (north of Tuscany)

In the morning of the 9th day start the road trip part of this Italy itinerary! Pick up the rental car in Florence and drive through the Chianti region to discover the birthplace of Italy's most famous wine. Drive through the Chianti Classico subregion with Castellina in Chianti, Gaiole in Chianti, Greve in Chianti and Radda in Chianti.

Finish the day with San Gimignano, a medieval town perched on a hill that could easily summarize all Tuscany by itself. Try not to arrive too late to see the town by day, especially its distinctive towers and historic centre, which is a UNESCO World Heritage Site.

Day 10: Siena

Continue your mini-road trip with Siena, a beautiful town whose medieval style contrasts with the Renaissance flamboyance of Florence. Most of it can be seen with one day of steady walking. We advise you to visit the Museo dell’Opera Metropolitana del Duomo and Siena Cathedral. If you have enough time you could also climb the Facciatone for an amazing view of Siena, especially Piazza del CampoPalazzo Pubblico and Torre del Mangia.

In the evening enjoy a great dinner (we vouch for La Taverna di San Giuseppe) followed by a few drinks on Piazza del Campo if you're up for it!

Day 11: Val d'Orcia (south of Tuscany)

Brace yourself for what many consider the most beautiful part of Tuscany: Val d'Orcia. The region was added to the list of UNESCO World Heritage Sites in 2004 to preserve its breathtaking landscapes characterized by hills of the most amazing green carefully flourished by vineyards and olive trees.
We would recommend to follow this road itinerary:
Siena > Asciano > Abbazia di Monte Oliveto Maggiore > MontalcinoAbbazia di Sant'Antimo > Bagno Vignoni > Pienza > Montepulciano.

This may seem like a lot of driving but it's really not that heavy. Also, you of course don't have to stop everywhere. The two abbazias (abbeys) are definitely worth the visit though. In the evening besides finding a good restaurant (which is an every day requisite in Italy!), look for an agriturismo (traditional farm) for the night. Depending on the season you may want to book it in advance. We warmly recommend Agriturismo Cerreto in Pienza.

Days 12-14: Rome

The last destination of this Italy itinerary in 2 weeks is Rome. Drop off the rental car the nearest as possible to Chiusure where you can then take a train to Rome (less than 2 hours). There are many places to see in Rome, hence it's important to have a well-thought plan and to book most of the attractions in advance.  Here's what we recommend:

Day 12 - morning: visit the historical centre of Rome around the Pantheon. Have a coffee at Sant'Eustachio Il Caffè that the New York Times once praised to serve the best coffee in the world.

Day 12 - afternoon: visit the Colosseum, the symbol of the Roman empire and its famous gladiatorial games. If you have time you may also want to check out the Palatino (Palatine Hill) and Foro Romano (Roman Forum).

Day 13: head to the Vatican very early in the morning (before 8 AM!) to have the unique pleasure of discovering Basilica di San Pietro (St. Peter's Basilica) and climbing the Dome without hordes of tourists around, like that's often the case later in the day. After that continue with the Chapel Sistine to see one of the world's most important and extraordinary work of art, the ceiling painted by Michelangelo.

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