9-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence

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Explore the best of Italy on a 9-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bologna, Siena, Rome, Florence, and Pisa. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Bologna, 1 night in Siena, 3 nights in Rome, and 2 nights in Florence. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Bologna, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of St. Peter's Basilica.

As you hit the open road and drive through Bologna, Siena, Rome, Florence, and Pisa, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Piazza Maggiore
Two TowersInternational Museum and Library of MusicPiazza Santo StefanoPorta Castiglione
Sistine ChapelSt Peter's BasilicaSaint Peter's SquareVatican Museums
Trevi FountainPiazza di Spagnapiazza del PopoloVia del CorsoVia dei Condotti
Altare della PatriaPantheonPiazza NavonaCastel Sant'AngeloTrastevere
Roman ForumColosseumVilla Borghese

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Day 1

Day 1

  • Bologna - Arrival day
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  • Piazza Maggiore
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Say hello to Bologna! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Bologna for 1 night before you continue your adventure!

Bologna is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Piazza Maggiore, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Bologna. Make yourself at home and enjoy some downtime before heading out again.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Bologna, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Ristorante Ciacco, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Ballarini, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sfoglia Rina, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

Raise a toast to the start of your 9-day road trip in Italy!

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Day 2

Day 2

  • Bologna
  • Siena
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Drive 170 km, 2 hours 32 min

  • Two Towers
  • International Museum and Library of Music
  • Piazza Santo Stefano
  • Porta Castiglione
  • More

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Two Towers is the first of them. Spend some time admiring this culturally significant monument before continuing your journey. International Museum And Library Of Music is your next stop. This intriguing museum is one of the best-rated sights in Bologna.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Santo Stefano. This culturally significant public square is a sight to behold. To round off your sightseeing experience, visit Porta Castiglione.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Siena's best restaurants.

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip in Italy!

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Day 3

Day 3

  • Siena
  • Rome
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Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
  • More

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Vatican City. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Start your adventure at Sistine Chapel. This top-rated chapel is a place that is appreciated by travelers and locals alike.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Saint Peter's Square. This popular square offers an enriching experience.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

Experience a taste of local culinary excellence while in Rome by securing a table at La Pergola. An esteemed 3-star Michelin restaurant, it features an exceptional mediterranean and contemporary menu. For an alternative taste experience, visit Il Pagliaccio, famous for its scrumptious creative and innovative dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Enoteca La Torre, a local favorite celebrated for its exquisite mediterranean and creative cuisine in Rome. Located in the heart of the city, this 2-star Michelin restaurant is an ideal pick for mediterranean and creative cuisine lovers seeking top-notch culinary experiences.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 4

Day 4

  • Rome
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Drive 9 km, 48 min

  • Trevi Fountain
  • Piazza di Spagna
  • piazza del Popolo
  • Via del Corso
  • Via dei Condotti
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Day 4 offers a multitude of experiences. You will stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

Via del Corso is one of the highlights of today. Take your time exploring this iconic street in Rome, which offers a perfect blend of history and culture. Plus, it's close to many other must-see landmarks.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Trevi Fountain. This world-famous monument is a romantic place to see in Rome. Continue your discovery at Piazza Di Spagna, a visually striking public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Popolo. This famous public square offers a romantic encounter with Rome.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Enjoy a lovely meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day in Italy!

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Day 5

Day 5

  • Rome
  • More

Drive 7 km, 47 min

  • Altare della Patria
  • Pantheon
  • Piazza Navona
  • Castel Sant'Angelo
  • Trastevere
  • More

Day 5 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the interesting Altare Della Patria, a culturally significant monument in Rome. Next, go to Pantheon.

After visiting Altare Della Patria and Pantheon, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to Piazza Navona. This grand public square offers a unique experience. Castel Sant'angelo is another noteworthy stop.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Don’t miss out on dining at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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Day 6

Day 6

  • Rome
  • Florence
  • More

Drive 283 km, 3 hours 38 min

  • Roman Forum
  • Colosseum
  • Villa Borghese
  • More

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

A blend of family-friendly attractions, scenic views, and picturesque spots await you in Rome on today’s itinerary. First up is the timeless archeological site, Roman Forum. Afterward, continue to Colosseum.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Villa Borghese. This astonishing park is an essential stop that should not be missed.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!

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Day 7

Day 7

  • Florence
  • More

Drive 4 km, 59 min

  • piazzale Michelangelo
  • Uffizi Gallery
  • piazza della Signoria
  • Ponte Vecchio
  • Oltrarno
  • More

On day 7 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

A visit to Oltrarno in Florence is a must on your agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Piazzale Michelangelo. This top-rated observation deck provides an insightful glimpse into the city's identity. Next, discover Uffizi Gallery, a historic art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Della Signoria, a famous public square. When you’re done, don’t forget to make a stop at the timeless Ponte Vecchio.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 8

Day 8

  • Florence
  • Bologna
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Drive 262 km, 3 hours 39 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • More

On day 8 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Florence and Pisa. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Start by visiting Cathedral Of Santa Maria Del Fiore, a prime spot to begin your journey. This history-steeped church is sure to impress. Next on your list is Central Market, another must-visit landmark and locally renowned food market renowned for its visually striking features.

While exploring and sightseeing, take time to savor the ambiance of Florence by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Leaning Tower Of Pisa. This UNESCO world heritage-designated monument is a remarkable attraction that offers a unique experience. Piazza Del Duomo, Pisa also adds charm to your journey.

At the end of the day, you will drive to Bologna, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Discover the culinary delights of Bologna by securing a reservation at Ahimè. Esteemed for its a Bib Gourmand award, this restaurant offers a remarkable selection of country cooking cuisine. For an alternative dining experience, try I Portici, renowned for its delicious creative and contemporary dishes. This esteemed 1-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Trattoria di Via Serra, a highly recommended local eatery celebrated for its mouthwatering emilian menu. With its Bib Gourmand recognition, it offers an unforgettable dining adventure.

After enjoying a fulfilling meal, continue your evening at Lime Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Macondo - Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Onda Marina By Night provides an excellent environment for a relaxed and enjoyable evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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Day 9

Day 9

  • Bologna - Departure day
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  • Portici di Bologna
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Day 9 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Bologna before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, begin at Portici Di Bologna. This worthwhile street is a popular place to see in the city.

On your last day in Italy, take time to indulge in shopping at Bologna’s popular marketplace, Quadrilatero. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bologna.

Have a fantastic dining experience at Va Mo Là, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria dal Biassanot offers an enticing alternative with its varied menu.

You’ll then say farewell to Bologna. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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