Two weeks in Italy: itinerary from OneTwoTrip travel expert

Two weeks in Italy: itinerary from OneTwoTrip travel expert

July 28, 2021 0 By TravelAdvisor

Photo: Cinque Terre

It may take more than one week to develop an interesting and eventful trip. But you can not waste your time, but entrust this work to a professional: OneTwoTrip employs travel experts who know everything about travel. Check out what a great trip we have made in Italy!

general information

Bologna – Rimini – San Marino – Montepulciano – Pienza – Pitigliano – Elba Island – Cinque Terre – Pisa

How much: from 63 320 ₽ for one when traveling together

The price includes hotels and return flights. Prices are presented for reference, OneTwoTrip is not responsible for their changes.

We advise you to rent a car for the entire trip. Since you are arriving in Bologna, it is most convenient to do it there. There are two options: at the airport or in the city near the central railway station, which can be reached from the airport by the BLQ bus (20 minutes on the way, the ticket costs 6 €).

Find flights to Bologna

Day 1. Bologna

Photo: Bologna

After arrival, do not waste time, go to the city for a walk in the historic center. Explore the streets full of interesting landmarks and monuments. Among them are arcades lining houses, towers, cathedrals, palaces and restaurants, where you should definitely try the traditional dishes of the Emilia-Romagna region.

Be sure to visit the University of Bologna – the oldest university in Europe, the first lectures began here in 1088.The main building of the university, Palazzo Poggi, is open to visitors. See frescoes and sculptures, the library and the wooden anatomical theater.

Address: Via Zamboni, 33. Entrance fee: 5 €

Also, see Santo Stefano, a complex of seven churches dating from the early Middle Ages.

Address: Via Santo Stefano, 24

After walking through Bologna, head to Rimini, where you will stay for a few days.

Days 1-5. Rimini

Photo: Rimini

Rimini is a resort on the Adriatic coast, the beach of which stretches for 15 kilometers. Most of the beaches are paid, but some are free. On a paid beach, renting a set of two sun loungers and an umbrella will cost about 20 € per day.

The conditions for a beach holiday in Rimini are wonderful: soft sand, the water warms up to 25 degrees in summer, a developed infrastructure with changing rooms and showers on the beaches. In addition to the beach, you should also pay attention to the city itself, where many architectural monuments have been preserved.

We have selected 3 options for hotels, different in cost and class:

  • Hotel Carnaby
  • Q Hotel
  • Savoia Hotel Rimini

Day 5. San Marino

Photo: San Marino
Photo: Rudy Balasko /

On the morning of the fifth day, travel to San Marino. By car, take the SS72 state road. The journey will take about 30 minutes.

San Marino is a state surrounded on all sides by the territory of Italy. It consists of 9 fortified towns. All major attractions are within walking distance.

On the territory of San Marino, tourists and travelers are carried by a small train, from the window of which you can enjoy the mesmerizing landscapes of the mini-state and its attractions. The cost of a 40-minute trip with an audio guide (available in Russian) is 7 € per person.

In the capital of the state of San Marino of the same name, stretching atop Mount Titano, walk through the squares and winding streets between stone houses. In Borgo Maggiore, travel to Piazza Grande for souvenirs and locally made silk and crystal products.

In the evening you can check into one of the San Marino hotels that we have selected

  • Hotel La Grotta
  • Hotel Rossi

Day 6. Transfer to Montepulciano

Photo: Tuscany

In Montepulciano you will drive through the Tuscany region. There are only 170 kilometers between the two cities, so take the time to stop and see small villages, vineyards, fields and fortresses. The main thing is not to get carried away and get to Montepulciano in the evening.

Days 7-8. Montepulciano

Photo: Montepulciano

Montepulciano is a beautiful town nestled among the picturesque valleys of the Tuscan region. The main street of the city, via di Gracciano nel Corso, pedestrianized. It houses souvenir shops, restaurants and wine cellars, some of which offer free wine tasting.

The main square of the city, Piazza Grande, houses the Cathedral of the Assumption of the Virgin. Opposite the cathedral is the Palace of the Commune, the upper platform of which can be reached for 2 €. An excellent view of the city and its surroundings opens up from there.

The city is famous for its wineries and cantinas. You can go on a guided tour to the wineries. For example, the Avignonesi winery offers visitors tastings, workshops and guided tours. For more information, visit the Avignonesi website.

In Montepulciano we offer one of the following accommodation options for 2 nights:

  • Palazzo Mosela Alla Porta
  • Il Tosco
  • Albergo Il Marzocco

On the morning of the eighth day, head towards the city of Pienza. The distance to it is 15 kilometers.

Day 8. Pienza

Photo: Pienza

Pienza is a renaissance city included in the UNESCO heritage list. It will take about two hours to get around it on foot. The streets of the city are buried in flowers, and cozy cafes beckon with their aromas. In Pienza, try sheep’s milk pecorino, one of the best cheese in Italy, and it goes well with local red wines.

After visiting Pienza, drive to Pitigliano. The trip will take about an hour and a half without stopping.

Days 8-10. Pitigliano

Photo: Pitigliano

Pitigliano is called the tuff city because of the many buildings and caves carved out of tuff. Pitigliano rises 315 meters above sea level. Narrow streets and secluded caves create a sense of peace and tranquility. This ancient city, surrounded by medieval walls, offers cozy shops, artisan workshops and historical sites for travelers. Explore the Pitigliano Cathedral, Orsini Palace, the Jewish Ghetto, and the Etruscan Roads under the roof of the cave.

In Pitigliano, we have selected 3 accommodation options, different in cost and class:

  • Hotel Scilla
  • Sovana Hotel & Resort
  • Locanda ilune

Early in the morning on the tenth day of the journey, drive to the coastal town of Piombino. The road to it will take about two hours. From there, take the ferry that will take you to Elba Island. You can find the ferry schedule and tariffs here.

Days 10-12. Elba Island


Photo: Portoferraio

Portoferraio is the capital of the island, which you will reach by ferry. In the city, you can visit the Museum-Villa San Martino – the former residence of Napoleon, where household items, weapons, family heirlooms and other values ​​have been preserved. Address: Localita San Martino, 57037 Portoferraio LI.

In the very center of Portoferraio stands the Cathedral of the Nativity of the Blessed Virgin Mary. It is famous for the fact that it was here that Napoleon was declared the emperor of the island. You can also visit the open-air museum. There are exhibited paintings, sculptures and panels. Address: Portoferraio – Loc.San Martino. The entrance is free.


Photo: Beach

There are more than 70 beaches on the island, most of which are sandy and pebble, and the other is sandy. The beaches are washed by the azure warm waters of the Mediterranean Sea, and picturesque cliffs and hills rise above them. You can climb the rocks on foot or by car and enjoy the Mediterranean scenery. The most beautiful beaches on the island are Barabarka, Le Gyaye, Cavoli, Paolina. By car, you can travel anywhere on the island and explore these and many other beaches.

On the Elbe, we have selected the following accommodation options for you:

  • Residenza Sant’Anna Del Volterraio
  • Marina Garden Hotel
  • Hotel Villa Ottone

On the morning of the twelfth day of the trip, leave the island and head to the Cinque Terre National Park. From Piombino, you can get there by car in about 2.5 hours.

Days 12-15. Cinque Terre

Photo: Manarola

The Cinque Terre is a national park made up of five UNESCO-listed villages: Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso. You can move between them by car, train or on foot. Travel time between villages varies from 20 minutes to 1.5 hours.


Riomaggiore is the largest town in the national park. There are picturesque colorful houses towering over the sea, a small pebble beach and a marina.


You can get from Riomaggiore to Manarola along the scenic Via dell’Amore. This village is similar to Riomaggiore, but has its own unique charm.


Corniglia is surrounded by vineyard-covered hillsides. This is the only village that does not have a beach or direct access to the sea.


In addition to colorful houses and a marina, you can see the Belforte Tower and the medieval Doria Castle.


Monterosso has a magnificent beach and stunning landscape.

In the Cinque Terre, we have selected several accommodation options for you:

  • Da baranin
  • Affittacamere le terrazze
  • Locanda valeria

Day 15. Return home

Photo: Pisa

On the morning of your last day, travel to Pisa Airport. Travel time to Moscow will be about 3 hours 30 minutes.

Expert advice

  • To plan your movements in and between cities, use the Rome2rio server
  • Convenient offline maps: and
  • If you want to get around Elba Island by car, please note that it can be transported by ferry. This is a paid service.
  • You can book and rent a car here.