Two weeks in Italy: route from travel expert OneTwoTrip

Two weeks in Italy: route from travel expert OneTwoTrip

It may take more than one week to plan an interesting and eventful trip. But you don’t have to waste your time, but entrust this work to a professional: OneTwoTrip employs travel experts who know everything about travel. Look what a great trip we had around Italy! 

General information

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

How much does it cost: from 63,320 ₽ per person when traveling together

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

We recommend renting a car for the entire trip. Since you are flying to Bologna, it is most convenient to do this there. There are two options: at the airport or in the city near the central railway station, where you can get from the airport by BLQ bus (20 minutes journey, ticket costs 6 €).

Day 1. Bologna

Two weeks in Italy: route from travel expert OneTwoTrip

After your arrival, don’t waste time, go into the city for a walk around the historical center. Explore the streets, which are home to many interesting sights and monuments. Among them are arcades stretching along houses, towers, cathedrals, palaces and restaurants, where you must try traditional dishes of the Emilia-Romagna region.

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

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

Also check out Santo Stefano, a complex of seven churches built during the early Middle Ages.

Address: Via Santo Stefano, 24 

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

Days 1–5. Rimini

Two weeks in Italy: route from travel expert OneTwoTrip

Rimini is a resort on the Adriatic coast, whose beach stretches for 15 kilometers. Most beaches are paid, but there are a few free ones. 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, water warms up to 25 degrees in summer, developed infrastructure with changing rooms and showers on the beaches. In addition to the beach, it is also worth paying attention to the city itself, where many architectural monuments have been preserved.

We have selected 3 hotel options, different in price and class:

  • Hotel Carnaby
  • Q Hotel
  • Savoia Hotel Rimini

Day 5. San Marino

Two weeks in Italy: route from travel expert OneTwoTrip

Photo: Rudy Balasko/

On the morning of the fifth day, go to San Marino. By car, take the SS72 highway. The journey will take approximately 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. 

Tourists and travelers are transported through the territory of San Marino by a 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 with the same name, located on the top of Monte Titano, take a walk through the squares and winding streets between stone houses. In Borgo Maggiore, head to Piazza Grande for souvenirs and locally made silk and crystal items.

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

  • Hotel La Grotta
  • Hotel Rossi

Day 6. Transfer to Montepulciano

Two weeks in Italy: route from travel expert OneTwoTrip

In Montepulciano you will travel through the Tuscany region. There are only 170 kilometers between the two cities, so take the time to stop to 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

Two weeks in Italy: route from travel expert OneTwoTrip

Montepulciano is a beautiful city located among the picturesque valleys of the Tuscan region. The main street of the city, via di Gracciano nel Corso, is pedestrian. There are souvenir shops, restaurants and wine cellars, some of which offer free wine tasting. 

On the main square of the city, Piazza Grande, is the Cathedral of the Assumption of the Virgin. Opposite the cathedral is the Palace of the Commune, the upper platform of which can be accessed for 2 €. From there you have an excellent view of the city and surrounding area.

The city is famous for its wineries and cantinas. You can go on a tour to the wineries. For example, the Avignonesi winery offers visitors tastings, master classes and excursions. Find more information on 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, move towards the city of Pienza. The distance to it is 15 kilometers.

Day 8. Pienza

Two weeks in Italy: route from travel expert OneTwoTrip


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

After visiting Pienza, go to Pitigliano. The trip will take about one and a half hours without stopping.

Days 8–10. Pitigliano

Two weeks in Italy: route from travel expert OneTwoTrip


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 feeling of peace and quiet. This ancient city, surrounded by medieval walls, offers travelers cozy shops, craft workshops and historical sites. See Pitigliano Cathedral, Orsini Palace, the Jewish Ghetto and Etruscan roads under the cave arch.

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 your trip, drive to the coastal city of Piombino. The road to it will take about two hours. 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


Two weeks in Italy: route from travel expert OneTwoTrip

Portoferraio is the capital of the island, where you will arrive by ferry. In the city you can visit the Villa San Martino Museum, the former residence of Napoleon, where household items, weapons, family heirlooms and other valuables 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 emperor of the island. You can also visit the open-air museum. There are paintings, sculptures and panels on display. Address: Portoferraio – Loc.San Martino. Admission is free.


Two weeks in Italy: route from travel expert OneTwoTrip

The island has more than 70 beaches, most of which are sandy and pebbly, while others are 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 cliffs on foot or by car and enjoy the Mediterranean scenery. The most beautiful beaches on the island are Barabarka, Le Guaye, Cavoli, Paolina. By car you can go anywhere on the island and explore these and many other beaches.

On 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 your trip, leave the island and head to the Cinque Terre National Park. You can get there from Piombino by car in about 2.5 hours.

Days 12–15. Cinque Terre

Two weeks in Italy: route from travel expert OneTwoTrip

The Cinque Terre is a national park consisting of five UNESCO heritage villages: Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso. You can travel 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 rising above the sea, a small pebble beach and a marina.


From Riomaggiore to Manarola you can get along the picturesque Road of Love (Via dell’Amore). This village is similar to Riomaggiore, but has its own unique charm.


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


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


Monterosso has a magnificent beach and amazing scenery.

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

  • Da Baranin
  • Affittacamere Le Terrazze
  • Locanda Valeria

Day 15. Returning home

Two weeks in Italy: route from travel expert OneTwoTrip

On the morning of your last day, head 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 wish to travel 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.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top