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

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Photo of panoramic view of Bologna,Italy.
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Photo of Fontana di Nettuno or Neptune fountain on Piazza Maggiore square at the morning dusk designed by Tommaso Laureti (1565).
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Photo of Basilica of SantApolinare in Classe.
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Bologna, Italy. View of Basilica di San Petronio on sunrise
Palazzo Re Enzo. Splendid cityscape of Bologna, Italy.
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Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
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photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
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Colosseum, Rome, Italy.
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Bridge Il Tevere a Ponte Vittorio Emanuele II in Rome, Italy.
Hadrian Mausoleum, Rome, Italy.
 Vatican dome of San Pietro and Sant Angelo Bridge, over Tiber river in Rome, Italy.
panoramic view of Rome and St. Peter's Basilica, Italy.
View of Pantheon in the morning, Rome, Italy.
Rome, Italy. Stunning twilight view of Forum ancient ruins, seen from Capitoline hill with Colosseum in background.
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Cozy old street in Trastevere in Rome, Italy. Trastevere is rione of Rome, on the west bank of the Tiber in Rome, Lazio, Italy. Architecture and landmark of Rome.
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photo of view of Roman Bridge of Cordoba, Rome, Italy.
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Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
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Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
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Experience the freedom of the open road in Italy as you embark on an unforgettable 6-day road trip! This experience caters to every traveler, featuring destinations like Bologna, Siena, Rome, and Florence.

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, 1 night in Rome, and 1 night 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 Pantheon are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Navona, learn more about the unique St. Peter's Basilica, and immerse yourself in the vibrant atmosphere of Vatican Museums.

As you hit the open road and drive through Bologna, Siena, Rome, and Florence, 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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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
La Piccola Venezia
Piazza MaggioreTwo TowersPiazza Santo StefanoBasilica of San DomenicoVilla Ghigi
Sistine ChapelSt Peter's BasilicaSaint Peter's SquareVatican Museums
Piazza NavonaPantheonTrevi Fountain
piazza della SignoriaCathedral of Santa Maria del FiorePonte VecchioUffizi Gallerypiazzale Michelangelo
Porta Castiglione

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Day 1

Day 1

  • Bologna - Arrival day
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  • La Piccola Venezia
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Welcome to Bologna, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night immersing yourself in Bologna's charm before embarking on the next leg of your journey.

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 La Piccola Venezia, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Bologna. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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.

Enjoy a lovely dining experience at Ristorante Ciacco, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Ristorante Ballarini, 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 Sfoglia Rina. It’s yet another ideal choice to enhance your time in Bologna tonight.

Cap off your dinner by heading to Bar Al Bricco D'oro, ideal for a leisurely evening with a drink in hand. Bar Freud E Squisito is another bar that offers an enjoyable setting. Similarly, Osteria Del Sole is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise a toast to the start of your 6-day road trip in Italy!

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Day 2

Day 2

  • Bologna
  • Siena
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Drive 170 km, 2 hours 37 min

  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • Basilica of San Domenico
  • Villa Ghigi
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On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.

Today’s itinerary in Bologna covers several incredible sights, including a public square, a monument, a church, a park and much more! Start your adventure at Piazza Maggiore. This famous public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the breathtaking wonders of Two Towers, a must-see monument in the city.

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 Piazza Santo Stefano. This worthwhile public square offers an enriching experience. For a change of pace, head to Basilica Of San Domenico, where you can take in heritage-rich features. Conclude your self-guided sightseeing tour with a visit to Villa Ghigi. These sights offer a fulfilling end to a perfect day.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Take some time to reflect on your day and savor another beautiful night 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
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On day 3 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 Vatican City. In the evening, you’ll end up in Rome, where you will stay for 1 night.

St. Peter's Basilica is your next stop. This wondrous major basilica is one of the best-rated sights in Siena.

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 Saint Peter's Square. To round off your sightseeing experience, visit Vatican Museums.

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.

Discover the culinary delights of Rome by securing a reservation at La Pergola. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of mediterranean and contemporary cuisine. For an alternative dining experience, try Il Pagliaccio, renowned for its delicious creative and innovative dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Enoteca La Torre, a highly recommended local eatery celebrated for its mouthwatering mediterranean and creative menu. With its 2-star Michelin recognition, it offers an unforgettable dining adventure.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

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

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Day 4

Day 4

  • Rome
  • Florence
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Drive 278 km, 3 hours 41 min

  • Piazza Navona
  • Pantheon
  • Trevi Fountain
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Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Get ready to discover some of the most iconic wonders in Rome, including a public square and a monument. Start your day at Piazza Navona. This history-steeped public square is a wondrous place to see in Rome. Then, wander over to Pantheon. If culturally significant sites excite you, this monument will be right up your alley. Nearby, you’ll also find Trevi Fountain. This romantic monument is a favorite among visitors.

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 you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Get a good night's sleep and look forward to another great day on the road in Italy!

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Day 5

Day 5

  • Florence
  • Bologna
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Drive 110 km, 2 hours 12 min

  • piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Uffizi Gallery
  • piazzale Michelangelo
  • More

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna. You’ll stay here for 1 night.

Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Piazza Della Signoria. This impressive public square is one of the top attractions in the city. Proceed to Cathedral Of Santa Maria Del Fiore, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Ponte Vecchio. This globally renowned historical landmark is a traveler-favorite. Not far away, you’ll find Uffizi Gallery, another key site on your sightseeing itinerary. Piazzale Michelangelo is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

If you’re not ready to end the night just yet, Lime Bar offers a perfect venue to relax and savor a drink. Similarly, Macondo - Cocktail Bar is well-suited for those looking to unwind in a social setting. Bar Onda Marina By Night is another excellent spot to enjoy a nightcap after a delightful meal.

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

  • Bologna - Departure day
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  • Porta Castiglione
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Day 6 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 Porta Castiglione. This increasingly popular monument is a popular place to see in the city.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Bologna's best shopping area, Via d'Azeglio. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy. Browse through boutiques to find unique and stylish fashion pieces to take home. Explore high-end stores offering an exquisite selection of luxury items.

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

If you're in the mood for something new, try Trattoria dal Biassanot, another premier location with a delectable 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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