Visit Italy in 2 weeks

You like cultural discoveries but also walks in nature? Do you dream of authentic Italy, from its big cities to its typical villages? You have 2 weeks of vacation ahead of you? This road trip will be perfect for you!

Starting from Florence you will discover Tuscany, Umbria and the capital city, Rome, along with all the beautiful landscapes in between. 

Here is a glimpse of the beautiful experiences awaiting in 2-week road trip in Italy:

• Take a cooking class in a Tuscan farm in Florence
• Walk on San Gimignano’s battlements
• Admire the beautiful Palazzo Pubblico and its surrounding monuments in Siena
• Take the time to watch the sunset over the Tiber river in Città di Castelo
• Visit the Roman theatre dating back from the 1st century, built just outside the city of Gubbio
• Hike along Passignano Lake and enjoy the beautiful scenery
• Discover Orvieto in an unusual way, by visiting its underground city 
• Visit the renown Colosseum and Vatican in Rome

To travel safely and without any worry on your mind, we recommend Chapka Insurance!

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2-week road trip in Italy

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Some practical information before your trip to Italy

 

For this itinerary, we recommend renting a car from Hertz. , It’s possible to rent it in one city and return it in another without exorbitant prices and limiting hidden costs.

You want to buy a paper travel guide? We recommend this one! In our opinion, it is the most complete, the most visual and the most up to date!

Need a road map to prepare your itinerary? We recommend this one, the most detailed and the most pleasant to read!

The best period for this 2-week road trip in Italy is from April to October. This country is worth a visit year-round, but during these months, it is when the weather is at its best. Except from July and August, it’s also a time period where there are not too many tourists. See more details here.

Italian food is known to be one of the best in the world, and you surely approve! This cuisine has spread all over the world, and most people have already tried it, pasta, ice cream, pizza, risotto… it keeps getting better! Instead, we would recommend for you to try out arancini, fontina, which is a great cheese, speck ham, focaccia, and taste a traditional and authentic tiramisu!

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Contents: 2-week road trip in Italy

1- Florence – Stop 1 of the 2-week road trip in Italy
2- San Gimignano – Stop 2 of the 2-week road trip in Italy
3- Siena – Stop 3 of the 2-week road trip in Italy
4- Città di Castelo – Stop 4 of the 2-week road trip in Italy
5- Gubbio – Stop 5 of the 2-week road trip in Italy
6- Passignano – Stop 6 of the 2-week road trip in Italy
7- Orvieto – Stop 7 of the 2-week road trip in Italy
8- Rome – Stop 8 of the 2-week road trip in Italy

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2-week road trip in Italy: step by step

 

What to do in Florence?

Florence is considered to be one of the most beautiful cities in Italy. An open-air museum, you will be charmed. 

• Visit the two main museums: the Uffizi Gallery and the Galleria dell’Accademia. The first one has famous artworks you won’t find anywhere else. In the second one, you will find the famous Michelangelo’s David.
• Discover the famous Piazza San Marco near the Galleria dell’Accademia. 
• Art lovers, make sure to go to the Palazzo del Bargello where you will find many Renaissance sculptures.
• Cross the Arno river on the Ponte Vecchio («Old Bridge» in Italian). You can’t come to Florence during this 2-week road trip in Italy without seeing it!
• Stroll around the gorgeous gardens of Boboli.
• You can not miss the Cathedral Santa Maria del Fiore, also called the Duomo.
• Go check the San Lorenzo Market out, your mouth will be watering with all the typical Italian products.
• Don’t hesitate to take a guided tour, it’s the best way to discover the city and its secrets!
• Taste Florence’s speciality: tripe.
• Admire the sunset from the Piazzale Michelangelo where you can get a panoramic view of the city.
• Treat yourself to a cooking class on a Tuscan farm. A unique experience that will surely become one of your best travel memories!

 

Where to sleep in Florence?

 

• Mid-range: Book one of the spacious rooms at Hotel Delle Nazioni and enjoy a hearty breakfast every morning. The hotel’s central location is ideal for visiting the city of Florence.
• High-end: Choose the Baglioni Relais Santa Croce and enjoy a night in a classically decorated 5-star hotel (frescoed ceilings, etc.). We love the rooms decorated with high quality period furniture. It is ideal to sublimate your stay in Florence.

 

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What to do in San Gimignano?

A village perched on a hill with typical Tuscan medieval architecture. You will adore San Gimignano.

• What would be a medieval town without battlements? Of course San Gimignano is surrounded by them, and you will enter the city by one of the ancient doors.
• Get lost in the streets of the city, and at the corner of a street enjoy a delicious Gelato in a traditional ice-cream shop.
• Admire the 13 remaining tower houses, originally the city had 75!
• Got to the Piazza del Duomo, the religious center of the village.
• Admire the Palazzo del Popolo, visit its art museum and head inside the Collegiate (or Duomo), the most important church in the city with its magnificent frescoes. You can buy your entrance tickets directly here to save time when you get there!
• San Gimignano is a stop on your 2-week road trip in Italy located in the heart of a wine region. We therefore advise you to take part in a vineyard tour followed by a wine tasting!

 

Where to sleep in San Gimignano?

 

• Mid-range: Stay in the heart of Italian culture at La Locanda di Quercecchio, a guesthouse located in a UNESCO listed building. It’s a great value for money in San Gimignano. If you prefer to be more independent, we recommend the great flat Home Sweet Home, where you will be welcomed like kings and queens, along with a very good breakfast.
• High-end: If you want even more comfort when staying in the city centre, book the Sangi Studio Apartment, with its warm decor and perfect location. Alternatively, you can go much higher up the scale by staying a little way out of town at the Casolare di Bucciano. An old restored farmhouse that represents everything you can imagine of a dream stay in Tuscany. Superb views, beautiful rooms, swimming pool, authenticity… it’s all there!

 

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What to do in Siena?

In the heart of Tuscany, Siena is a city of art and culture.

• If you visit Siena in summer, arrange to be there on July 2nd or August 16th and you will have the chance to attend the famous Palio delle Contrade, a horse race organized on the central square, Piazza del Campo. An unforgettable experience!
• Apart from this event, Piazza del Campo is also to be seen for its particular architecture: it is slightly curved and amphitheater-shaped.
• You will also discover the Palazzo Pubblico and its Torre del Mangia from which you will have an incredible view of the city.
• The Cattedrale di Santa Maria Assunta or Sienna Duomo an impressive marble cathedral, is also a must. Inside, you will be amazed at the beautiful sculptures and paintings that decorate it.
• Explore the many streets of the city center, discover the hidden treasures of the city and find a small traditional restaurant for dinner.
• And if you want to visit a museum, the city has many museums of art and history to familiarize you with the Italian culture.

 

Which activities to do in Siena?

 

• If you want to discover the old town and its secrets, we recommend you to take a guided tour, like this one for example.
• If you have always dreamed of cooking authentic Italian dishes, take part in a cooking class in a farm in the heart of the Chianti region.
• Treat yourself to a wine and olive oil tasting on this stop of your 2-week road trip in Italy.

 

Where to sleep in Siena?

 

• Mid-range: Sleep in a historic 15th-century building in the centre of Siena at B&B San Francesco. The hosts are lovely, the rooms are clean and comfortable, the breakfast is great, we recommend it! If you prefer good value for money, but a more modern establishment, head for the Best Western Hotel San Marco.
• High-end: Treat yourself to all the comfort and authenticity of the Italian way by staying at the Casatorre dei Leoni Dimora Storica. Friendly and helpful staff, with a delicious breakfast, we love it! For a little more peace and quiet, move away from the city centre to the Villa del Sole Siena, with its comfortable rooms and beautiful rooftop.

 

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What to do in Città di Castelo?

Small town of the 16th century, Città di Castelo is installed on the valley of the Tiber. It is the birthplace of the beautiful Monica Bellucci.

• Visit the Pinacoteca Comunale, a museum of Italian art with works by Raffaello, Signorelli or Domenico Ghirlandaio: the most important museum in Umbria.
• Stroll around the city and explore all its nooks.
• Take the time to enjoy an ice cream while admiring the beautiful architecture of the city.
• Go to the Arborologia Arborea, a social organization that saves old fruit species: apples, pears, cherries, peaches, figs… Come meet the passionate owners and enjoy tasting delicious local fruits.
• Sit down along the Tiber and admire the sunset in a wonderful setting. It will become a very nice memory of your 2-week road trip in Italy.

 

Where to sleep in Città di Castelo?

 

• Mid-range: Stay in the centre of town, in a beautiful 15th-century building, at the Residenza Antica Canonica. You will be welcomed like royalty by the staff, who will also be able to recommend good places to eat. To top it all off, you will sleep in very comfortable rooms.
• High-end: Sleep in the heart of the city in the comfort of a 4-star hotel combining historical buildings and modern decor at Hotel Tiferno. If you want to take advantage of your holiday to get some fresh air, stay at Agriturismo La Tana, where authenticity, comfort and conviviality are the order of the day! Bikes are available to rent, so you can also explore the surrounding area at your own pace.

 

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What to do in Gubbio?

A very beautiful city all in height, with many alleys to discover. You will love the small town of Gubbio, fifth stop of your 2-week road trip in Italy.

• Take the cable car to the top of Mount Ingino to enjoy a panoramic view of the surroundings and the beautiful botanical garden.
• In Piazza Grande, visit the Palazzo dei Consoli, a Gothic style palace built in the 14th century. Today it is a museum where works and artifacts of the Roman time are showcased.
• Discover the Roman Theater outside the walls of the city, built in the 1st century BC. It could welcome up to 6000 people!
• Lose yourself in the beautiful streets of the city, meet locals on a terrace with a coffee.

 

Where to sleep in Gubbio?

 

• Mid-range: Sleep in the annex of the Ducal Palace, in the comfort of a 4-star hotel, the Relais Ducale. Ideally located in the historic centre, with traditionally decorated rooms, some of which offer a beautiful view of the city, and a caring staff, everything is there to have a regenerating stay.
• High-end: The Vescovado 7 is the perfect accommodation to enjoy great comfort in the city centre. You will feel like you are immersed in Italian culture. If you prefer to get away from the city centre and sleep in charming, well-equipped and absolutely beautiful establishments, we recommend L’ira di Dante or Nikis Resort. You’ll be hearing from us!

 

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What to do in Passignano?

A small village on Lake Tasimeno, enjoy this stop of your 2-week road trip in Italy to relax and rest.

• Discover the remains of this ancient medieval city, make your imagination work and experience the medieval life of Passignano.
• Go for a hike along the lake, enjoy the calm of nature to relax and why not picnic on the shore.
• For dinner you can choose from a few restaurants in the city. We recommend choosing fish caught in the lake.
• A 20-minute drive (on the road to Orvieto), visit the village of Castiglione del Lago, a medieval town with a magnificent fortress, the Rocca del Leon and a Renaissance palace : Palazzo della Corgna, now an art museum.

 

Where to sleep in Passignano?

 

• Mid-range: Stay in peace and quiet by the lake, with a great view of the sunset, when booking The View Sunset & Relax. It’s the perfect place to rest after a great day of sightseeing.
• High-end: Live in a haven of peace for a few days at Antico Casale Tiravento. Swimming pool, breathtaking views, garden, clean, spacious and nicely decorated rooms, what more could you ask for!

 

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What to do in Orvieto?

Medieval city built on a volcanic rock, Orvieto will be your last stop in the quiet of Umbria before reaching the capital.

• Want an unusual visit? Go on a guided tour of the underground city of Orvieto! You will be impressed by the extent of the cavities. It will be an out of the ordinary experience during your 2-week road trip in Italy.
• At the top of the Orvieto hill, you will not be able to miss the Cathedral, an impressive Gothic building. Its mosaic facade will leave you speechless.
• Morbid atmospheres do not scare you? Visit the Necropolis of the Tufa Crucifix built by the Etruscan people in the 8th century BC.
• Archeology lovers, visit the National Archaeological Museum of Orvieto, you will discover the remains and artifacts of the region.

 

Where to sleep in Orvieto?

 

• Mid-range: Experience Italian authenticity in the city centre by staying at B&B La Casa Di Tufo. Blending modernity and tradition, with attentive hosts, this is a great place to stay. If you prefer a charming establishment with a beautiful garden and swimming pool just 2km away from Orvieto, don’t hesitate and book the Agriturismo Podere Pescara.
• High-end: At Domus Festina Lente you can sleep in the great comfort of a renovated flat, with a modern decoration but having kept its historical charm, all in the centre of Orvieto. To enjoy your last stop in the beautiful nature of Umbria, we can only recommend accommodations a little further from the city centre but offering a high standard, such as Misia Resort or Altarocca Wine Resort Adults Only. They are ideal for resting before visiting the capital.

 

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What to do in Rome?

The City of the Seven Hills, Rome is the most popular city in Italy and you’ll quickly understand why. It blends past and present in a magnificent way. It truly is a great way to end your 2-week road trip in Italy. 

• Has anyone ever gone to Rome without going to the Colosseum? No! It’s THE iconic building of the city, just imagine when there used to be gladiators fighting, the crowd cheering …
• Eat a pizza in Rome’s historic district.
• Be sure to check out the Palatine Hill and get a beautiful view from the top.
• Discover the Pantheon and its beautifully decorated interior, as well as its special way to get the light in.
• When visiting Rome, you have to go to the Vatican. Artistic masterpiece, be sure to check the Sistine Chapel out.
• Go see the Pope telling the mass in front of St. Peter’s Basilica.
• Don’t hesitate to take a guided tour to discover the city, that’s how you’ll learn the little details of history.
• Enjoy a cannoli at the Valzani pastry shop in Trastevere district. If you want to taste other specialities, we advise you to take part in a food tour, another way to discover the city!

 

Where to sleep in Rome?

 

• Mid-range: Just 600 metres from the Trevi Fountain and a 10-minute walk from the Colosseum, the central location of the Quirinale Luxury Rooms is perfect. In addition, the service is good, the rooms are modern and the breakfast is great!
• High-end: In the heart of Rome, enjoy Italian luxury at the Singer Palace Hotel, which has a rooftop restaurant with stunning views of the Roman city. This hotel is elegant, refined and will help make your stay in Rome unforgettable!

 

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Learn more about your road trip in Italy…

 

• You want to know all the information about the country? It’s here.
• Then, to rent a car at the best price, we advise you this website.
• Finally, to book a flight at the best price, we advise you this website.
• You are looking for a great travel insurance for your 2-week road trip in Italy? We recommend this one!

 

Do not hesitate to share your trip with us, we can’t wait to hear all about your adventures!

 

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If you have any information, good tips, or simply a comment about this itinerary, please don’t hesitate to leave a comment below! The whole team will be happy to hear from you!