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

On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, 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 Rome, and meet locals along the way!

No visit to Rome is complete without Villa Borghese. This top-rated park is one of the top attractions in the city. Proceed to Spanish Steps, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Di Spagna. This timeless public square is a traveler-favorite. Not far away, you’ll find Colosseum, another key site on your sightseeing itinerary. Roman Forum is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

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.

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 mediterranean and creative foodies seeking culinary excellence.

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.

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.

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

Day 3 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Let Circus Maximus set the tone for the day. Spend some time admiring this picture-perfect archeological site before continuing your journey. Pantheon is your next stop. This world-famous monument 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 Navona. This visually striking public square is a sight to behold. To round off your sightseeing experience, visit Campo De' Fiori and Castel Sant'angelo.

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

Treat yourself to a shopping spree in Rome at Trastevere. Stroll through stylish boutiques and shops, where you can browse unique items to take home. Pick up souvenirs for your loved ones, including artisan crafts that beautifully showcase the culture of Italy. After shopping, explore what Trastevere has to offer, connecting you with locals or fellow travelers as you check out its attractions, available services, and seasonal events.

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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

Keep the excitement of the evening going by visiting a bar or two. The Apartment Bar Roma is an excellent place to start. You could also check out Hotel Hassler Roma, offering a different kind of charm.

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

Day 5 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Bologna for 6 nights.

Piazza Del Campo leaves a lasting impression. This public square is one of the most spectacular places to visit in Siena. Next, head to Siena Cathedral, a popular church, known for its enchanting 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 Fontebranda. This standout historical landmark is a highly recommended experience. Nearby, you'll also find Basilica Of San Domenico and Fortezza Medicea (siena) Visit these for an interesting touch to your journey.

When you’re not exploring beautiful places, you can relax in Bologna. Here, you can choose from the best hotels and other accommodations as you get to know more about the culture in the city.

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.

Have a memorable dining experience in Bologna by booking a table at Ahimè, 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 consistently earns high praises, 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 in Bologna for its delicious emilian cuisine. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

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.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 6 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!

Make a stop at Palazzo Re Enzo. This intriguing palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Fountain Of Neptune, Bologna located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Bologna Cathedral. Its breathtaking features will captivate you. After the church, continue your tour of the city with a visit to Piazza Maggiore. Visitors usually appreciate the visually striking features of this public square. Next up is Basilica Of San Domenico, a highly recommended church.

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.

Enjoy a lovely dining experience at Bononia Cafè, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Via Con Me, 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 Trattoria Pizzeria La Mela. It’s yet another ideal choice to enhance your time in Bologna 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.

After savoring a delicious meal, step into the vibrant nightlife at Lime Bar, where the evening is just getting started. In the same way, Macondo - Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Bologna. Bar Onda Marina By Night is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

On day 7 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Whatever your travel style is, Porta Santo Stefano is an essential stop in Bologna. This intriguing monument provides an insightful glimpse into the city's identity. Next, discover Porta Castiglione, a culturally significant monument, promising a delightful encounter.

Continue your sightseeing with a visit to Arco Del Meloncello, a worthwhile monument.

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 Bologna to find the best options for you!

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.

Savor the flavors at Va Mo Là, a top pick for dinner tonight. Alternatively, Trattoria dal Biassanot beckons with its unique menu offerings. Also, consider Ristorante Enoteca da Lucia. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

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

If you’re not ready to end the night just yet, Aurum offers a perfect venue to relax and savor a drink. Similarly, Bar Senza Nome is well-suited for those looking to unwind in a social setting. Caffè Ristretto is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 8 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Awaiting your discovery is the underrated Devotional Portico Of St. Luke, a symbolic monument in Bologna. Next, go to Palazzo Pallavicini.

After visiting Devotional Portico Of St. Luke and Palazzo Pallavicini, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Chiesa Del Santissimo Salvatore. This stunning church offers a unique experience.

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 delightful dinner at Pappare' - Bologna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mister Coffee Bistrò? It's another excellent option with a diverse menu. Consider reserving a table at All'Osteria Bottega as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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.

To truly maximize your evening out, consider visiting Bar Piratello after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Carlo, another bar with an inviting ambiance. Similarly, Bar Maurizio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 9 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!

Faizan-e-madina Bologna brings Bologna's character to life. This inviting mosque is a highlight of any visit in the city. Then, enjoy Botanical Garden And Herbarium, another mesmerizing attraction that never fails to captivate visitors. Next, head over to Pinacoteca Nazionale Di Bologna, one of the city’s most underrated attractions, known for its respected features.

If you’re looking for more, spend time soaking in the atmosphere of San Martino. This culturally significant church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

Italy makes the perfect setting for a calming but fun road trip experience. 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.

Enjoy a lovely meal at Ristorante Rodrigo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, CDH Hotel Bologna is another top choice with a popular menu. You could also check for a table at Victoria Station. As an establishment that consistently gains high praises from customers, it’s an ideal choice 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.

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

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 10 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Two Towers is an ideal stop early in the day. This well-known monument is a must-visit in the city. When you’re ready for your next discovery, continue to International Museum And Library Of Music, which may be one of the most photogenic 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 Piazza Santo Stefano, a frequently visited public square in the city.

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 Trattoria da Me, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Botanica Lab Cucina, another top spot with a tantalizing menu. You might also want to secure a reservation at Café de la Paix. 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.

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

On day 11 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 2 hours 11 min. When you arrive in Pisa, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Knights' Square and explore the historic features. Next, make your way to Leaning Tower Of Pisa, another highlight in Pisa. When you’re done exploring the monument, continue to Piazza Del Duomo, Pisa, a historic public square.

Nearby, you will also find Pisa Cathedral. This underrated church is a top place to see in the area.

Continue your laid-back road trip in Italy as you make your way to Florence. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

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.

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

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.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Florence is brimming with adventures.

One of the most world-famous attractions included on the itinerary is Ponte Vecchio. This romantic historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Uffizi Gallery and learn what makes this historic art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the famous Piazza Della Signoria. After exploring the public square, head to Galleria Dell'accademia. This well-known art gallery is a highlight in Florence.

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 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.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 13 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. 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 Florence!

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Make time for Piazzale Michelangelo, a famous observation deck that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of Santa Croce In Florence, enchanting visitors with its heritage-rich appeal. Continue your exploration at Pitti Palace. This palace is one of the city’s most well-known spots.

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

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.

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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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

Explore the vibrant nightlife at Gosh* after your meal, a hub for lively evenings and memorable moments. Or, head to Antico Caffè Del Moro - Art Bar Firenze for a great selection of flavorful drinks and a charming setting. Furthermore, Quelo Bar is perfect for those looking to extend their night with a touch of local flavor.

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

Day 14 of your relaxed road trip in 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!

Make a stop at Cathedral Of Santa Maria Del Fiore. This widely recognized church is a must-visit for travelers looking for a unique holiday experience. Make your way to Central Market located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Basilica Di Santa Maria Novella, Firenze (fi). Its culturally significant features will captivate you.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Arezzo. 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 15 min. Upon reaching Arezzo, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Spend your afternoon discovering Piazza Grande, a locally renowned public square known for its visually striking features.

After a day of exploration, relax at one of the top hotels or accommodations in Rome. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip in Italy.

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.

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.

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

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