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

Day 2 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!

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and natural wonders. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Villa Borghese is the first of them. Spend some time admiring this remarkable park before continuing your journey. Spanish Steps is your next stop. This spectacular public square is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Di Spagna. This history-steeped public square is a sight to behold. To round off your sightseeing experience, visit Colosseum and Roman Forum.

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.

Get ready for an unforgettable culinary journey in Rome by reserving a table at La Pergola. Renowned as a 3-star Michelin restaurant, it offers an exceptional mediterranean and contemporary menu. For a different taste experience, head to Il Pagliaccio, recognized for its delicious creative and innovative dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Enoteca La Torre, a local favorite known for its delightful mediterranean and creative cuisine in Rome. Nestled in the heart of the city, this restaurant with 2 Michelin star is an ideal choice for discerning mediterranean and creative foodies seeking culinary excellence.

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

Continue your evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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

On day 3 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 1 night, 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!

Set out on a day brimming with fun adventures, breathtaking views, and picturesque spots. Start at the locally renowned Circus Maximus, a historic archeological site in Rome. Next, go to Pantheon.

After visiting Circus Maximus and Pantheon, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to Piazza Navona. This visually striking public square offers a unique experience. Campo De' Fiori is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Castel Sant'angelo, one of the most history-steeped places to visit in Rome.

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 Rome.

Enjoy a delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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

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

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience 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 Bologna, where you’ll stay at a top-rated hotel of your choice for 6 nights.

Today’s agenda in Siena includes a public square, a church, a historical landmark, a monument and much more! Piazza Del Campo is must-visit public square and a great starting point for the day. Next, continue your journey to Siena Cathedral, a well-known church, located just a leisurely stroll away. Next, head to Fontebranda, a romantic historical landmark, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. If you’re looking for more, Basilica Of San Domenico is also a frequently visited attraction that is worthwhile a visit. Lastly, don’t miss Fortezza Medicea (siena), a curiosity-inducing gem to see 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.

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 Bologna.

Have a memorable dining experience in Bologna by booking a table at Ahimè, renowned as a Bib Gourmand restaurant presenting an exceptional country cooking menu. For a different culinary experience in Bologna, I Portici shines as one of the top destinations, known for its delicious creative and contemporary cuisine. This 1-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Trattoria di Via Serra is known as a top local spot for its delicious emilian cuisine in Bologna. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

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

Keep the excitement of the evening going by visiting a bar or two. Bar Al Bricco D'oro is an excellent place to start. You could also check out Bar Freud E Squisito, offering a different kind of charm. A last recommendation for the day is Osteria Del Sole. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Day 6 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 palace, a monument, a church, a public square and much more! Palazzo Re Enzo is must-visit palace and a great starting point for the day. Next, continue your journey to Fountain Of Neptune, Bologna, a locally appreciated monument, located just a leisurely stroll away. Next, head to Bologna Cathedral, a photogenic 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 Bologna. If you’re looking for more, Piazza Maggiore is also an astonishing attraction that is worthwhile a visit. Lastly, don’t miss Basilica Of San Domenico, a worthwhile gem to see in the city.

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

Savor the flavors at Bononia Cafè, a top pick for dinner tonight. Alternatively, Via Con Me beckons with its unique menu offerings. Also, consider Trattoria Pizzeria La Mela. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

Before calling it a day, visit one of the best bars in Bologna. 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 Lime Bar, ideal for a leisurely evening with a drink in hand. Macondo - Cocktail Bar is another bar that offers an enjoyable setting. Similarly, Bar Onda Marina By Night is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 7 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!

Bologna is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and historic treasures! Start at Porta Santo Stefano, an increasingly popular monument that is worthwhile a visit in the city. Nearby, you’ll find Porta Castiglione, enchanting visitors with its heritage-rich appeal. Continue your exploration at Arco Del Meloncello. This monument is one of the city’s most often recommended spots.

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

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 wonderful meal at Va Mo Là, a top-rated dining spot in Bologna. If you're in the mood for something new, try Trattoria dal Biassanot, another premier location with a delectable menu. You might also want to book a table at Ristorante Enoteca da Lucia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

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

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.

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.

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 3 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 Bologna, and meet locals along the way!

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a monument, a palace, and a church. Begin your adventure at Devotional Portico Of St. Luke. This is an increasingly popular monument you should not miss. Another must-see is Palazzo Pallavicini, an underrated palace in Bologna.

When you’re ready for the next sight, head to Chiesa Del Santissimo Salvatore.

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!

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 lovely meal at Pappare' - Bologna, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Mister Coffee Bistrò is another top choice with a popular menu. You could also check for a table at All'Osteria Bottega. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna 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.

After enjoying a fulfilling meal, continue your evening at Bar Piratello, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Carlo offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Maurizio provides an excellent environment for a relaxed and enjoyable evening.

Soak in the unique atmosphere of Bologna 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!

Day 9 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Savor the day by visiting some of the best places to see in Bologna, including a mosque, a botanical garden, an art gallery, a church and much more! Start your adventure at Faizan-e-madina Bologna. This intriguing mosque is a must-visit for travelers looking for a unique holiday experience. Make your way to Botanical Garden And Herbarium located in Bologna for an enchanting atmosphere.

Next, immerse yourself in the setting of Pinacoteca Nazionale Di Bologna. Its respected features will captivate you. After the art gallery, continue your tour of the city with a visit to San Martino. This church has a culturally significant 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.

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.

Make sure to reserve a table at Ristorante Rodrigo, 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 CDH Hotel Bologna, 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 Victoria Station, 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, 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.

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

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

Day 10 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!

Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming city of Bologna. Your adventure starts at Two Towers, a locally renowned local hot spot. Another notable attraction to explore is International Museum And Library Of Music. This frequently visited museum is known for its historic appeal.

After soaking in the highlights of these sights, take some time to wander Bologna's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Santo Stefano. This history-steeped public square offers a fascinating experience that many visitors find memorable.

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 the food culture in Bologna 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.

Don’t miss out on dining at Trattoria da Me, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Botanica Lab Cucina, another top spot with a mouthwatering menu. You might also want to secure a reservation at Café de la Paix. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

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.

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

Day 11 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!

Bologna is home to plenty of attractions that offer fun adventures, breathtaking views, and picturesque spots! Start at Knights' Square, a locally appreciated public square that is worthwhile a visit in the city. Nearby, you’ll find Leaning Tower Of Pisa, enchanting visitors with its picture-perfect appeal. Continue your exploration at Piazza Del Duomo, Pisa. This public square is one of the city’s most world-famous spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pisa Cathedral.

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.

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 an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.

After dinner, it’s time to fall in love with the amazing nightlife in Florence and unwind at some of the best bars in the city.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

On day 12 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!

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Florence on today’s itinerary. First up is the timeless historical landmark, Ponte Vecchio. Afterward, continue to Uffizi Gallery, an art gallery every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Della Signoria. This top-rated public square is an essential stop. Following that, head to Galleria Dell'accademia, another must-visit site that will enhance your experience. Don’t forget to stop by David, a well-known statue in the city.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Florence 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 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.

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.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

Day 13 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.

Start by visiting Piazzale Michelangelo, a prime spot to begin your journey. This visually striking observation deck is sure to impress. Next on your list is Basilica Of Santa Croce In Florence, another must-visit landmark and locally renowned church renowned for its culturally significant 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 Pitti Palace. This romantic palace is a remarkable attraction that offers a unique experience. The Boboli Gardens 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 Florence. There are so many fun and eye-opening activities to try out in Florence 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 Florence to find the best options for you!

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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

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.

Toast to another unforgettable and relaxing road trip adventure in Italy!

Day 14 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Rome 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, romantic experiences, and scenic views. Start at Cathedral Of Santa Maria Del Fiore, a widely recognized church in the city. Then, head to Central Market and soak in the ambiance of this eye-catching food market.

There are many interesting places to see in Florence and when you are ready for more, go to Basilica Di Santa Maria Novella, Firenze (fi). This is one of the city’s most locally renowned spots. After exploring the church, visit the notable Piazza Grande.

You’ll be staying at the incredible city of Rome 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 Rome, explore the city like a local by trying out the best restaurants in the area.

Have a fantastic dining experience at Sofitel Roma Villa Borghese, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Centro offers an enticing alternative with its varied menu. Additionally, Ristorante Tema is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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.

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