Relaxed 9-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Florence

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Sit back and enjoy a relaxed 9-day road trip in Italy with this laid-back self-drive vacation.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Bologna, Florence, Siena, San Gimignano, Pisa, and Lucca. Make yourself at home at top-rated hotels and stay 3 nights in Bologna and 5 nights in Florence. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.

Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Bologna, you’ll collect your rental car of choice. From there, you’ll begin your 9-day journey across Italy and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.

We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Ponte Vecchio. Another highlight of this self-drive tour is the captivating Leaning Tower Of Pisa.

Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Piazza Del Duomo, Pisa. With this travel plan, you could also soak in the atmosphere of the memorable Piazzale Michelangelo. Get close to the spectacular Cathedral Of Santa Maria Del Fiore and the wonderful Piazza Della Signoria. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.

Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 8 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 9 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 9-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Church of the Holy Savior
Palazzo d'AccursioPiazza MaggioreBologna CathedralFountain of Neptune, Bologna
Basilica of Santa Croce in FlorenceBargello National MuseumPalazzo VecchioUffizi GalleryPonte Vecchiopiazza della Signoria
Galleria dell'AccademiaCathedral of Santa Maria del FiorePalazzo PittiThe Boboli Gardenspiazzale MichelangeloOltrarno
Fortezza MediceaBasilica of San DomenicoSiena Cathedralpiazza del CampoTower of MangiaPubblico Palace
Chiesa di Sant'AgostinoRocca di MontestaffoliPiazza del Duomo, San GimignanoTown Hall, Picture Gallery and Great TowerSanGimignano1300Porta San Giovanni

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Day 1

Day 1

  • Bologna - Arrival day
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  • Church of the Holy Savior
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Your relaxed road trip through Italy starts when you reach the incredible city of Bologna, where you'll stay for 2 nights. You'll pick up your rental car in Bologna and begin your adventure in Italy.

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 Chiesa Del Santissimo Salvatore, 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.

Treat yourself to a delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Hang out and unwind at some of the top bars in Bologna.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Bologna as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Bologna
  • More

Drive 0.5 km, 7 min

  • Palazzo d'Accursio
  • Piazza Maggiore
  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • More

Day 2 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Bologna!

Start by visiting Palazzo D'accursio, a prime spot to begin your journey. This breathtaking palace is sure to impress. Next on your list is Piazza Maggiore, another must-visit landmark and widely recognized public square renowned for its enchanting features.

While exploring and sightseeing, take time to savor the ambiance of Bologna by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Bologna Cathedral. This breathtaking church is a remarkable attraction that offers a unique experience. Fountain Of Neptune, Bologna also adds charm to your journey.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Bologna to find the best options for you!

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a delicious dinner at Bononia Cafè, an excellent option for tonight's dining. Looking for something different? Via Con Me offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Pizzeria La Mela. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Experience the amazing nightlife in Bologna and unwind at the coolest bars in the city.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Lime Bar, a well-loved spot among locals and tourists. Or, head to Macondo - Cocktail Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Onda Marina By Night, another top-rated place in the area.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

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Day 3

Day 3

  • Bologna
  • Florence
  • More

Drive 111 km, 1 hour 59 min

  • Basilica of Santa Croce in Florence
  • Bargello National Museum
  • Palazzo Vecchio
  • Uffizi Gallery
  • Ponte Vecchio
  • piazza della Signoria
  • More

Day 3 of your relaxed road trip across the beautiful country of Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most notable attractions included on the itinerary is Basilica Of Santa Croce In Florence. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Bargello National Museum and learn what makes this heritage-rich museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Palazzo Vecchio. After exploring the palace, head to Uffizi Gallery. This top-rated art gallery is a highlight in Bologna. Lastly, don’t forget to check out the wondrous Ponte Vecchio. Enjoy exploring this incredible historical landmark at your own pace.

After a day of exploration, relax at one of the top hotels or accommodations in Florence. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Enjoy a lovely dining experience at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Florence.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Cherish every minute of your relaxed road trip vacation across Italy.

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Day 4

Day 4

  • Florence
  • More

Drive 11 km, 1 hour 15 min

  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • Palazzo Pitti
  • The Boboli Gardens
  • piazzale Michelangelo
  • Oltrarno
  • More

Day 4 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Oltrarno is a fantastic place you can explore today in Florence. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Florence-way-of-life and visit all the nearby sights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Galleria Dell'accademia. This locally renowned art gallery provides an insightful glimpse into the city's identity. Next, discover Cathedral Of Santa Maria Del Fiore, a grand church, promising a delightful encounter.

Continue your sightseeing with a visit to Pitti Palace, a locally renowned palace. When you’re done, don’t forget to make a stop at the captivating The Boboli Gardens. Round off your day at Piazzale Michelangelo, another gem in Florence with history-steeped features to discover.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Before calling it a day, visit one of the best bars in Florence. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Soak in the unique atmosphere of Florence as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday in Italy!

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Day 5

Day 5

  • Florence
  • More

Drive 154 km, 2 hours 53 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Pubblico Palace
  • More

On day 5 of your relaxed road trip across Italy, you’ll explore the area around Florence, where you’ll be staying for another 3 nights. With so many fun and inspiring experiences to offer, a tour of Florence will make you fall even more in love with the city and uniqueness of Italy.

Today’s agenda in Florence includes a monument, a church, a public square, a palace and much more! Fortezza Medicea (siena) is must-visit monument and a great starting point for the day. Next, continue your journey to Basilica Of San Domenico, an up-and-coming church, located just a leisurely stroll away. Next, head to Siena Cathedral, a breathtaking church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. If you’re looking for more, Piazza Del Campo is also a famous attraction that is worthwhile a visit. Lastly, don’t miss Tower Of Mangia, a curiosity-inducing gem to see in the city.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

If you feel like it, head out to a bar to celebrate another fantastic day in Florence and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

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Day 6

Day 6

  • Florence
  • More

Drive 119 km, 2 hours 24 min

  • Chiesa di Sant'Agostino
  • Rocca di Montestaffoli
  • Piazza del Duomo, San Gimignano
  • Town Hall, Picture Gallery and Great Tower
  • SanGimignano1300
  • Porta San Giovanni
  • More

Your laid-back and relaxed road trip in Italy continues on day 6, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Florence and beyond. With 2 nights left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Chiesa Di Sant'agostino. This culturally significant church is sure to ignite your curiosity. Next, dive into the history-steeped features of Rocca Di Montestaffoli, a must-visit castle in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Piazza Del Duomo, a locally appreciated public square. For a change of scene, check out Palazzo Comunale, Pinacoteca, Torre Grossa, known for its historic features.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Enjoy a lovely meal at Tijuana, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Djària - American Bar is another top choice with a popular menu. You could also check for a table at The Florence Irish Pub. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Hang out and unwind at some of the top bars in Florence.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

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Day 7

Day 7

  • Florence
  • More

Drive 177 km, 2 hours 58 min

  • Knights' Square
  • Leaning Tower of Pisa
  • Angelo Caduto
  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Battistero di San Giovanni
  • More

On day 7 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in Pisa destinations, just outside of the city. You still have 1 night left in Florence. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Just a short distance away is Leaning Tower Of Pisa, an UNESCO world heritage-listed monument that draws visitors from far and near.

Continue your journey to Angelo Caduto, one of the city’s most beloved spots that you shouldn’t miss. Another great site to visit is the beloved Pisa Cathedral. Last up on today’s itinerary is a public square. Make your way to Piazza Del Duomo, Pisa for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Florence.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a lovely dining experience at Ristorante Buca Niccolini, 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 Essenziale, 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 Ristorante La Grotta Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Florence!

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Day 8

Day 8

  • Florence
  • Bologna
  • More

Drive 236 km, 3 hours 21 min

  • Walls of Lucca
  • Piazza Napoleone
  • San Michele in Foro
  • Piazza dell'Anfiteatro
  • Guinigi Tower
  • St Martin Cathedral
  • More

Day 8 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Bologna for 1 night.

Start by visiting Mura Di Lucca, a prime spot to begin your journey. This romantic historical landmark is sure to impress. Next on your list is Piazza Napoleone, another must-visit landmark and interesting public square renowned for its romantic 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 San Michele In Foro. This breathtaking church is a remarkable attraction that offers a unique experience. Piazza Dell'anfiteatro also adds charm to your journey, and Guinigi Tower wraps up your day with its grand appeal.

In the city of Bologna, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Make sure to reserve a table at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

As the day is coming to an end, stop at some of Bologna’s best bars to celebrate this day of your slow-paced adventure in Italy.

Continue your lively evening at Aurum, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Senza Nome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Ristretto ensures a night out tailored to your taste.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

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Day 9

Day 9

  • Bologna - Departure day
  • More
  • Two Towers
  • More

Day 9 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Bologna.

Make the most of your final day in Italy by visiting Bologna’s iconic markets and shopping establishments in the buzzing Via d'Azeglio. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. You can also browse through boutiques for stylish fashion choices. Elevate your style with pieces from high-end retail stores.

If you're up for some more sightseeing, begin at Two Towers. This interesting monument is a popular place to see in the city.

Unwind and look back at the past 9 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Bologna or just grab something light to keep you going.

Give yourself enough time to wave goodbye to Bologna and begin your journey home. The unforgettable experiences you’ve collected along your 9-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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