Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Siena, Rome, and Florence

Day 2 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Today’s agenda in Bologna includes a monument, a museum, and a public square. Two Towers is must-visit monument and a great starting point for the day. Next, continue your journey to International Museum And Library Of Music, an intriguing museum, located just a leisurely stroll away. Next, head to Piazza Santo Stefano, a photogenic public square, also available for your discovery today.

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.

Start your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

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.

Unwind after your meal by stepping into Lime Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Macondo - Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Onda Marina By Night, another top-rated bar in the area.

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

Day 3 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!

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazza Maggiore. This top-rated public square is a history-steeped place to see in Bologna. Continue your discovery at Palazzo Del Podestà, Bologna, a photogenic palace with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Fountain Of Neptune, Bologna. This often recommended monument offers a symbolic encounter with Bologna. Palazzo Re Enzo is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

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.

Bring home unique finds from Bologna's bustling shopping hub, Galleria Cavour. Enjoy a leisurely exploration of unique high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Galleria Cavour offers plenty of options, including primary services, unique landmarks, and community events.

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 Va Mo Là, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Trattoria dal Biassanot, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Enoteca da Lucia. With a reputation for consistently satisfying customers, it’s a perfect 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.

Keep the excitement of the evening going by visiting a bar or two. Aurum is an excellent place to start. You could also check out Bar Senza Nome, offering a different kind of charm. A last recommendation for the day is Caffè Ristretto. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

Day 4 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!

Today, you'll explore some of the most beautiful places in Bologna, including a church, a monument, and a palace. Start your day with a visit to Chiesa Del Santissimo Salvatore. This worthwhile church is a must-visit in the city. When you’re ready for your next discovery, continue to Tombs Of The Glossators Of Bologna, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Bologna on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Palazzo Pallavicini, one of the city’s most locally appreciated palace.

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

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 Siena.

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena 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 Siena. The bars in Siena make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

Day 5 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 Siena. By the end of the day, you’ll drive in the direction of the city of Rome, where you’ll stay at a top-rated hotel of your choice for 5 nights.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await. Siena Cathedral is the perfect place to start. This church is one of the most well-known places to visit in Siena. Next, head to Opera Delle Metropolitana, an often recommended museum, known for its historic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Del Campo. This romantic public square offers a unique experience that is highly recommended. Meanwhile, Tower Of Mangia adds its own distinct charm to your journey.

Continue your laid-back road trip exploration of the best attractions in Italy at Rome. Select from top hotels and accommodations in the city to recharge and rejuvenate.

Exploring the food culture in Rome offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended place to eat in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition and a delicious mediterranean and creative menu.

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

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.

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

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, 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 Rome, and meet locals along the way!

Start by visiting Castel Sant'angelo, a prime spot to begin your journey. This romantic castle is sure to impress. Next on your list is Campo De' Fiori, another must-visit landmark and astonishing public square renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the ambiance of Rome by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Piazza Navona. This romantic public square is a remarkable attraction that offers a unique experience. Pantheon also adds charm to your journey, and Trevi Fountain wraps up your day with its romantic appeal.

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.

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.

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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

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.

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

Day 7 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

A blend of fun adventures, picturesque spots, and history-rich sites await you in Rome on today’s itinerary. First up is the well-known archeological site, Largo Di Torre Argentina. It's a standout spot that offers a memorable visit. Afterward, continue to Altare Della Patria. A visit to this monument is an enriching experience for all.

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 Roman Forum. This globally renowned archeological site is an essential stop that should not be missed. Following that, head to Colosseum, another must-visit site that will enhance your experience. Lastly, visit Circus Maximus and learn why this archeological site is renowned as one of the city's most popular attractions.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Rome offers a wide selection of experiences for every traveler.

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 Rome.

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.

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 Rome. The bars in Rome make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

Day 8 of your relaxed road trip through Italy means 24 hours of making the best memories in Rome. You’ll go sightseeing at famous attractions in Rome. 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 Rome!

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Foro Italico. This heritage-rich sports complex is sure to ignite your curiosity. Next, dive into the eye-catching features of Villa Borghese, a must-visit park 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 Piazza Del Popolo, a famous public square. For a change of scene, check out Piazza Di Spagna, known for its romantic features.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Rome. There are so many fun and eye-opening activities to try out in Rome 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 Rome to find the best options for you!

Exploring the food culture in Rome offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Dine in style at Sofitel Roma Villa Borghese, a top recommendation for dinner tonight. Or, for a change of pace, Centro boasts a menu that's sure to impress. Also, be sure to check out Ristorante Tema. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

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

On day 10 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

After soaking in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Orvieto. Expect your car journey to take a minimum of 1 hour 38 min. When you arrive in Orvieto, it's time to take a break from the road.

Savor the rest of your day by heading to Orvieto Cathedral, a locally renowned church that draws visitors from near and far. When you're done, continue on to Museo Dell'opera Del Duomo, where you can soak in the photogenic surroundings.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Orvieto. Your travel time is around 1 hour 38 min.

Your self-guided tour starts at Well Of St. Patrick, a well-known monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

In the city of Florence, 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.

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 Florence, explore the city like a local by trying out the best restaurants in the area.

Experience a harmony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Known for its 3-star Michelin status, Enoteca Pinchiorri offers a delightful variety of dishes highlighting its delicious italian contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Santa Elisabetta, a highly recommended restaurant known for its enticing creative and mediterranean cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Gucci Osteria da Massimo Bottura, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and international menu.

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

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.

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

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, where you'll stay for 2 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Cathedral Of Santa Maria Del Fiore. This impressive church provides an insightful glimpse into the city's identity. Next, discover Piazza Della Repubblica, a romantic public square, 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 widely recognized Uffizi Gallery. Round off your day at Ponte Vecchio, 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.

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 Florence, explore the city like a local by trying out the best restaurants in the area.

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.

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.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 12 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Basilica Di Santa Maria Novella, Firenze (fi). This enchanting church is a highlight of any visit in the city. Then, enjoy Central Market, another photogenic attraction that never fails to captivate visitors. Next, head over to Galleria Dell'accademia, one of the city’s most captivating attractions, known for its detailed features.

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 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.

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

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.

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

Day 13 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Bologna for 1 night. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, photo-friendly spots, and history-rich sites. Start at Basilica Of Santa Croce In Florence, a notable church in the city.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Pisa. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 23 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

One of our top recommendations for your sightseeing is Leaning Tower Of Pisa. Spend some time admiring the culturally significant features of the monument before you continue to your next stop. Then, head to Piazza Del Duomo, Pisa. This globally renowned public square is a traveler-favorite in the city.

When you’re not exploring beautiful places, you’ll have a relaxed time at Bologna. 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.

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. Also, be sure to check out All'Osteria Bottega. Known as a local hotspot, it’s a great choice for tonight in Bologna.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

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

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