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

Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
All inclusive app
Travel agent
24/7 fast service

Description

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!

Read more

Itinerary summary

See a summary of the itinerary that you can fully customize

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

Personalize your itinerary

Customize tours under each day and destination

Day 1

Day 1

  • Bologna - Arrival day
  • More
  • Church of the Holy Savior
  • More

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.

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.

Have a fantastic dining experience at Ristorante Ciacco, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Ballarini offers an enticing alternative with its varied menu. Additionally, Sfoglia Rina is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

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

After your meal, keep the night alive at a bar like Bar Al Bricco D'oro, known for its lively atmosphere. Bar Freud E Squisito is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Osteria Del Sole offers an excellent atmosphere for those looking to amp up the 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.

Read more
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 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a palace, a public square, a church, a monument and much more! Begin your adventure at Palazzo D'accursio. This is an up-and-coming palace you should not miss. Another must-see is Piazza Maggiore, an impressive public square in Bologna.

When you’re ready for the next sight, head to Bologna Cathedral. From there, take a leisurely stroll to Fountain Of Neptune, Bologna, another of the city’s increasingly popular attractions.

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.

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

Enjoy a delicious meal at Bononia Cafè, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Via Con Me, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Lime Bar, known for its inviting atmosphere. Macondo - Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Bar Onda Marina By Night provides a great setting to enjoy the night away.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across Italy.

Read more
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 Italy promises an exciting agenda full of discovery. You’ll end your day in the city of Florence, where you’ll stay for 5 nights.

Discover a day packed with fun adventures, photo-friendly spots, and history-rich sites in Bologna. Begin your sightseeing with Basilica Of Santa Croce In Florence. This popular church is one of the top attractions in the city. Proceed to Bargello National Museum, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Palazzo Vecchio. This captivating palace is a traveler-favorite. Not far away, you’ll find Uffizi Gallery, another key site on your sightseeing itinerary. Ponte Vecchio is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Della Signoria and uncover why it's recognized as one of the city's most top-rated attractions.

When you’re not exploring beautiful places, you’ll have a relaxed time at Florence. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

A leisurely self-drive holiday in Florence can’t get any better than this! Toast to another amazing day in Italy!

Read more
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

On day 4 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, where you'll stay for 4 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Florence, and meet locals along the way!

At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Galleria Dell'accademia. This heritage-rich art gallery is a highlight of any visit in the city. Then, enjoy Cathedral Of Santa Maria Del Fiore, another history-steeped attraction that never fails to captivate visitors. Next, head over to Pitti Palace, one of the city’s most popular attractions, known for its enchanting features.

If you’re looking for more, spend time soaking in the atmosphere of The Boboli Gardens. This history-steeped botanical garden is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazzale Michelangelo, an impressive observation deck, and take a stroll around the area.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

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 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.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Florence. The bars in Florence make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Read more
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

Your laid-back and relaxed road trip in Italy continues on day 5, 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 3 nights left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Get ready to discover some of the most iconic wonders in Florence, including a monument, a church, a public square, a palace and much more! Start your day at Fortezza Medicea (siena). This culturally significant monument is an increasingly popular place to see in Florence. Then, wander over to Basilica Of San Domenico. If historic sites excite you, this church will be right up your alley. Nearby, you’ll also find Siena Cathedral. This culturally significant church is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Del Campo is an impressive spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the picture-perfect Tower Of Mangia. Take a moment to appreciate the fascinating details of this curiosity-inducing monument. Wrap up your self-guided tour of Florence's top attractions with a visit to Pubblico Palace.

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.

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

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.

Following your dinner, dive into the local bar culture at Gosh*. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Antico Caffè Del Moro - Art Bar Firenze, the perfect place for those looking to experience the best of the nightlife. Similarly, Quelo Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Read more
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

On day 6 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in San Gimignano destinations, just outside of the city. You still have 2 nights 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.

Today’s itinerary in Florence covers several incredible sights, including a church, a castle, a public square, a museum, a monument and much more! Start your adventure at Chiesa Di Sant'agostino. This underrated church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Rocca Di Montestaffoli, a must-see castle in the village.

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 Del Duomo. This worthwhile public square offers an enriching experience. For a change of pace, head to Palazzo Comunale, Pinacoteca, Torre Grossa, where you can take in UNESCO world heritage-listed features. Conclude your self-guided sightseeing tour with a visit to Sangimignano1300 and Porta San Giovanni. These sights offer a fulfilling end to a perfect day.

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.

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across Italy.

Read more
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 across Italy, you’ll explore the area around Florence, where you’ll be staying for another 1 night. 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.

Discover a day packed with fun adventures, breathtaking views, and picturesque spots in Florence. Begin your sightseeing with Knights' Square. This beloved public square is one of the top attractions in the city. Proceed to Leaning Tower Of Pisa, 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 Angelo Caduto. This often recommended point of interest is a traveler-favorite. Not far away, you’ll find Pisa Cathedral, another key site on your sightseeing itinerary. Piazza Del Duomo, Pisa is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Battistero Di San Giovanni and uncover why it's recognized as one of the city's most beloved attractions.

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.

Savor the flavors at Ristorante Buca Niccolini, a top pick for dinner tonight. Alternatively, Essenziale beckons with its unique menu offerings. Also, consider Ristorante La Grotta Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Read more
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 easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Lucca. By the end of the day, you’ll drive in the direction of the city of Bologna, where you’ll stay at a top-rated hotel of your choice for 1 night.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Mura Di Lucca. This history-steeped historical landmark is sure to ignite your curiosity. Next, dive into the romantic features of Piazza Napoleone, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to San Michele In Foro, a frequently visited church. For a change of scene, check out Piazza Dell'anfiteatro, known for its romantic features. We also recommend visiting Guinigi Tower. This monument is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to St Martin Cathedral, yet another underrated attraction in Florence.

You’ll be staying at the incredible city of Bologna in this laid-back road trip in Italy. You'll stay here for 1 night.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Bologna, explore the city like a local by trying out the best restaurants in the area.

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. Additionally, Ristorante Enoteca da Lucia is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Bologna. The bars in Bologna make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Round off your dining experience by visiting Aurum, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Senza Nome, a bar catering to every mood and preference. Caffè Ristretto likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

Read more
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.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Bologna's best shopping area, Quadrilatero. 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.

If you're up for some more sightseeing, begin at Two Towers. This well-known 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.

Dine in style at Pappare' - Bologna, a top recommendation for dinner tonight. Or, for a change of pace, Mister Coffee Bistrò boasts a menu that's sure to impress.

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.

Read more

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.