The Pentagonal Road Trip - Italy

The Pentagonal Road Trip - Italy

The happiness arising from the freedom of a road trip has no match. The winding mountain roads, the coastlines, UNESCO heritage sites, architecturally stunning towns, driving through Italy is definitely going to bring series of flukes. Plan a 11 day long trip and witness northern Italy like never before, creating and carrying memories for lifetime.

Driving Itinerary


Min Travelling Time

Florence to Genoa

227 Km

2 hours 51 minutes

Genoa to Milan

145 Km

2 hours 7 minutes

Milan to Venice

270 Km

2 hours 59 minutes

Venice to Bologna

154 Km

1 hour 58 minutes

Bologna to Florence

108 Km

1 hour 40 minutes

Day 1 and Day 2

For this trip, you essentially have 2 options to choose from - You can rent one car for all the destinations while taking this Florence to Florence round trip OR in case you are planning to take only one or two destinations of the listed trip, you can rent a one-way car to save time. Go for one as per your need and let the journey begin!


The adventure starts in Florence, the eighth most populous city of Italy. The capital of Italy’s Tuscany region, Florence is home to numerous masterpieces of Renaissance architecture and art. Discover it to the fullest by wheeling around the city in complete freedom with a rental car.

Things to do - Places to visit in Florence

  • The Duomo Cathedral : This magnificent cathedral is the 4th largest in the world.
  • Pitti Palace : A gallery complex exhibiting vast collection of Italian & European masters art
  • Uffizi Gallery : Italy’s top visited museum, located in the historic center of Florence.
  • Bargello Museum : This present art museum was once used as barracks and prison.
  • Accademia : An art museum, best known as home of Michelangelo's sculpture David.
  • San Miniato al Monte : One of the finest Romanesque structures, offering scenic view of the city.

Places to stay in Florence

For your stay, you essentially have 3 options to choose from :

  • Historic Center : This small yet large center of the city is easily walkable from 1 end to the other, having almost all of the main sights you’ll be visiting in Florence.
  • Within the City : Staying the night in Florence but outside the center would not only be light on your wallet, but will also provide you the option to stay close to locals and hence understand the culture better.
  • Surrounding Countryside: Choosing to stay outside the city, you can enjoy the benefit of being close to the city as well as the pleasure of relative peace of the countryside.

Places to eat in Florence

Feed your taste buds the best of Italian and multi cuisine dishes at some of the famous cafes or restaurants such as SENZ'ALTRO Bistrot, Panini Toscani, The Cut Steakhouse and Mangius. You can also dine with a local chef at Patrizia of La Cucina di Pat and Monia of Nella Cucina Della Gatta.

Day 3 and Day 4

From Florence, leave at dawn for your next destination, Genoa. On your way, you may like to take stops at a few places such as Ponte Vecchio, Pisa and Cinque Terre for some breathtaking views and delicious food.


By the time it’s day 3’s dusk, you’ll reach Genoa. One of the Italy’s underrated gems, Genoa city is rich in architecture and art (opulence and shingle), offering an undiluted sense of history. Explore the city and beyond in complete freedom and in total ease with a car rental.

Things to do - Places to visit in Genoa

  • Palazzo Blanco : Witness Old World masterpieces along with fine examples of the Genoese School of Art.
  • Porto Antico : A rejuvenated waterfront zone with Europe’s largest aquarium along with museum, botanical garden, shops and restaurants.
  • Genoa’s Royal Palace : Designated as UNESCO World Heritage site, this gorgeous palace offers some great grand structures.
  • Galleria Nazionale di Palazzo Spinola : Another UNESCO World Heritage site, this art museum offers a lot to witness including local events.
  • Laghi del Gorzente : A group of 3 lakes surrounded by mountains, offering a mesmerising view. Ideal location for peace lovers.
  • Boccadasse : A beautiful spot along the sea. Nearby the beach are some good restaurants along with a picturesque fishing village.

Places to stay in Genoa

The area of your stay in Genoa depends entirely on what you are looking for. You can choose the perfect place for your stay from the followings :

  • Molo and Maddalena : The medieval and the baroque districts, Molo and Maddalena, form up the heart of the city, offering age-old historic centre and incredible architectural works.
  • Porto Antico : Stretching as long as 22 km, this largest port of Italy offers aquariums, museum devoted to ocean, marinas, restaurants offering lip smacking food and array of bars.
  • Boccadasse : This small fishing village with picturesque looks, is a great place to stay. Away from the hustle and bustle of the city, this place is a mixture of quiet, pleasure and charm.

Places to eat in Genoa

It is said that a good and tasty meal makes your mood light and keeps you energised. Have mouth licious food at some of the best places to eat in Genoa. You can go for fine dining at Scalvini or have the local cuisine at Al Marmo, get cheap eats at Paradiso di Nervi or GranRistoro.

Day 5 and Day 6

Check-out from your hotel in the morning of day 5, get back to your rental car and leave for your next destination, Milan. Plan your driving itinerary in such a way that you don’t miss out Sunset at Duomo di Milano Cathedral in Milan. On your way to the destination, you may like to take a few stops at the nearby attractions such as Italian Riviera, Serravalle Scrivia, Pontecurone and Versilia.


Drive yourself to the global capital of fashion and design and the financial hub of Italy known for high-end restaurants and shops. Travel around the city exploring some of the best architectural work on earth in complete freedom, at your very own terms, with a rental car.

Things to do - Places to visit in Milan

  • Duomo di Milano : One of the largest cathedral in Italy and Europe, Duomo, is the symbol of Milan in the world.
  • Santa Maria delle Grazie : UNESCO World Heritage site containing painting of The Last Supper by Leonardo da Vinci.
  • Sforza Castle : 15th century citadel, built by Duke of Milan, with a museum and showcasing art by da Vinci and Michelangelo.
  • Teatro alla Scala : Originally known as the Nuovo Regio Ducale Teatro alla Scala, the opera house showcases finest artistic performances.
  • Pinacoteca di Brera : Witness some of the world’s most stunning, centuries-old paintings from many Italian Masters such as Raphael.
  • The Museo Civico di Storia Naturale di Milano : National History museum of Milan displaying preserved animals, minerals, fossils and skeletons.

Places to stay in Milan

Regarding your stay in Milan, you can choose any of the below mentioned areas :

  • San Lorenzo : Just to the south and west of the Duomo lies the most romantic neighbourhood, small and quiet, around the Piazza and nearby Basilica.
  • Brera : If you’re looking for an area full of sightseeing options, Brera is the place for you. The tangle of narrow streets, immediate northwest to the city center.
  • Navigli District : This area is meant for those who love nightlife. It offers Milan’s most vibrant party scenes with dozen of bars, restaurants and shops.

Places to eat in Milan

Milan offers some of the finest eateries in the world. From local to multi cuisine, there are numerous fine dining restaurants, cafes, moderately and cheap priced eating joints such as LAMO - The Restaurant, L'Immagine Ristorante Bistrot, Maison Touareg and TheLab - Unconventional Burger Experience.

Day 7 and Day 8

After staying up 2 days at Milan, get back into your car rental and head all the way to the next destination, Venice. Plan your driving itinerary in such a way that you reach the city early morning to catch the scenic sunrise at the Lido.


The city of water, known by various other names such as Floating City, City of Bridges, Queen of Adriatic etc., is flooded with tourists throughout the year. The Lagoon and a part of the city has been listed as UNESCO World Heritage Site. Since the city has got no roads but canals, people commute using boats. Park your rental, and travel around this unique city, exploring it to the fullest.

Things to do - Places to visit in Venice

  • Piazza San Marco : la Piazza, the principal public square of Venice, also known as St Mark’s Square (in English).
  • Doge’s Palace : A gothic style palace and museum featuring prison, room of Duke and armoury tours.
  • Saint Mark’s Basilica : One of the best examples of Italo-Byzantine architecture, it is most famous of all the churches in Venice.
  • Burano : The place with colourful houses, fishing island, a lace museum and lip smacking seafoods.
  • Lido di Venezia : Host to Venice Film Festival, this place offers lagoons, seaside resorts and beaches.
  • Teatro La Fenice : One of the most renowned landmarks of Italian Theater, it is an opera house with sitting capacity of 1,000 viewers.

Places to stay in Venice

For your stay in Venice, you can choose any of the following areas :

  • At the core : The area covered by San Marco, Dorsoduro and San Polo & Santa Croce, encompasses most of Venice’s attractions.
  • In the city : Staying at Giudecca, Castello or Cannaregio would be as good as staying at the center as the city’s size is very small.
  • Closeby : If you wish to be a bit easy on your pocket, you can choose to stay at Lido di Venezia or Mestre (main land).

Places to eat in Venice

The taste of food of Venice is as amazing as the city. Varying from Seafood to Chinese, Italian to Japanese, Fine dining to Cheap eateries, you have endless options to feed yourself. You can try Al Colombo, La Palanca, Giardino di giada, Impronta and Cocaeta - Non le solite Crepes for the yummiest dishes.

Day 9 and Day 10

It’s time to say goodbye to the city of Venice. Get back in your rental car and head all the way to the last destination left, the city of Bologna. Leave Venice early morning and reach Bologna by dusk, visiting and relaxing at a few places such as Padua and Ferrara, on your way.


The seventh most populous city, Bologna is the capital of Emilia-Romagna Region in Northern Italy. One of the wealthiest cities of Italy, Bologna is a famous tourist destination with many medieval and renaissance structures. Wheel around in total ease and explore the city at your own terms with a car rental in Bologna.

Things to do - Places to visit in Bologna

  • Piazza Maggiore : A square with classic buildings, cafes and arched colonnades such as City Hall, Fountain of Neptune etc.
  • Palazzo d'Accursio : This 14th century Town Hall offers many interesting things including a fresco-filled chapel & fine art museum.
  • Basilica of San Domenico : One of the most popular historic church with artworks, paintings and remains of Saint Dominic.
  • Parco Gessi Bolognesi e Calanchi dell'Abbadessa : A nature reserve with wild boar, scenic views and mountains.
  • Villa Ghigi : Witness mesmerising views of Bologna and the countryside from a lush green space.
  • Teatro Anatomico : Archiginnasio Municipal Library and the Anatomical Theatre that was once the main building of the University of Bologna.

Places to stay in Bologna

The best three areas to stay in Bologna are mentioned below, choose the most suitable one for yourself :

  • At the core : Centro Storico, the city center of Bologna, compact, walkable and full of medieval charm. Best option to choose if you wish to stay close to everything.
  • Around Bologna Centrale Station : Located to the north of the city’s historic centre,

Hotels in this area tend to be cheaper than those in the Centro.

  • Around Fiera di Bologna : A commercial and business centre area especially suitable for business and congress travellers. It is cheaper and has good public transport connections.

Places to eat in Bologna

Quality and taste of food at different restaurants and cafes of Bologna is beyond impressive. Have lip smacking dishes at Fine Dining, Local Cuisine, Cheap Eats and Moderately priced places such as Ristorante Garganelli, Trattoria di Via Serra, Breaking Toast, Bistro Domino, Taj Mahal Ristorante Indiano and Naama Cafe.

Day 11

The very last day of your trip to northern Italy. Get back to your car rental as early as possible and head all the way to your pick-up city, Florence. On this road trip from Bologna to Florence, a journey full of scenic views, you can find many attractions on the way such as Siena, Orvieto and Crete Senesi. This 11 day long trip would be a lifetime thing that can be best enjoyed with a car rental. Reserve one for yourself in advance, and get a car of your choice for the best price.

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