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!

To truly experience Rome, make sure to drop by Villa Borghese. This impressive park is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Spanish Steps, one of the city’s best highlights.

Next, check out Piazza Di Spagna, one of the most globally renowned places to see in Rome. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Colosseum. Wander around and soak in the culturally significant atmosphere this archeological site offers. Then, head to Roman Forum, a top-rated archeological site that adds another dimension to your day.

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.

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

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

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

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

Day 3 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!

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.

Catch Circus Maximus before the crowds roll in. This stunning archeological site is sure to ignite your curiosity. Next, dive into the culturally significant features of Pantheon, a must-visit monument 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 Navona, a wondrous public square. For a change of scene, check out Campo De' Fiori, known for its picture-perfect features. We also recommend visiting Castel Sant'angelo. This castle is a must for anyone looking to experience the city to the fullest.

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!

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.

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 a lovely dining experience at Hotel de Russie, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at La Taverna Italiana, 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 The Parrot Bar. It’s yet another ideal choice to enhance your time in Rome tonight.

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

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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

Day 5 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Siena and end it in Bologna. You’ll stay in Bologna for 6 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Catch Piazza Del Campo before the crowds roll in. This history-steeped public square is sure to ignite your curiosity. Next, dive into the romantic features of Siena Cathedral, a must-visit church 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 Fontebranda, a curiosity-inducing historical landmark. For a change of scene, check out Basilica Of San Domenico, known for its historic features. We also recommend visiting Fortezza Medicea (siena). This monument is a must for anyone looking to experience the city to the fullest.

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

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.

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

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.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

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.

Bologna is brimming with adventures.

Palazzo Re Enzo is must-visit palace and a great option for a daytime tour of the area. Continue your journey to Fountain Of Neptune, Bologna, an intriguing monument, located just a leisurely stroll away. Next, head to Bologna Cathedral, a stunning 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. When you're ready, let your sightseeing route take you to the famous Piazza Maggiore. If you’re looking for more, Basilica Of San Domenico is also a curiosity-inducing attraction that is worthwhile a visit.

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.

Don’t miss out on dining at Bononia Cafè, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Via Con Me, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. 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, 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.

Keep the excitement of the evening going by visiting a bar or two. Lime Bar is an excellent place to start. You could also check out Macondo - Cocktail Bar, offering a different kind of charm. A last recommendation for the day is Bar Onda Marina By Night. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Porta Santo Stefano is perfect for a self-paced visit during the day. This photogenic monument is sure to impress. Next on your list is Porta Castiglione, another must-visit landmark and up-and-coming monument renowned for its symbolic features.

While exploring and sightseeing, take time to savor the culture of Bologna by sampling some local delicacies. When you’re ready for more sightseeing, head to Arco Del Meloncello. This picture-perfect monument is an essential place to visit for anyone looking for the full Bologna experience.

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.

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.

Enjoy a lovely meal at Va Mo Là, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria dal Biassanot is another top choice with a popular menu. You could also check for a table at Ristorante Enoteca da Lucia. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Bologna tonight.

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.

After your meal, keep the night alive at a bar like Aurum, known for its lively atmosphere. Bar Senza Nome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Ristretto offers an excellent atmosphere for those looking to amp up the evening.

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

Day 8 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!

Awaiting your discovery is the up-and-coming Devotional Portico Of St. Luke, a visually striking 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 photogenic 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 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.

Enjoy a delicious meal at Pappare' - Bologna, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Mister Coffee Bistrò, another top spot with a mouthwatering menu. You might also want to secure a reservation at All'Osteria Bottega. 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.

Continue your evening by exploring the vibrant nightlife scene at Bar Piratello, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Carlo, a bar that offers unique local touches. Likewise, Bar Maurizio 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!

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

Let Faizan-e-madina Bologna set the tone for the day. Spend some time admiring this sacred mosque before continuing your journey. Botanical Garden And Herbarium is your next stop. This increasingly popular botanical garden is one of the best-rated sights in Bologna.

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 Pinacoteca Nazionale Di Bologna. This instagrammable art gallery is a sight to behold. To round off your sightseeing experience, visit San Martino.

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!

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 Ristorante Rodrigo, a top pick for dinner tonight. Alternatively, CDH Hotel Bologna beckons with its unique menu offerings. Also, consider Victoria Station. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

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

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

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

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!

Your adventure in Bologna is only getting started when you visit Two Towers, an interesting local hot spot. Another notable attraction to explore is International Museum And Library Of Music. This worthwhile museum is known for its instagrammable 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 romantic public square offers a fascinating experience that many visitors find memorable.

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.

Make sure to reserve a table at Trattoria da Me, 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 Botanica Lab Cucina, 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 Café de la Paix, a hidden gem nestled in Bologna. 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 Bologna.

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

Day 11 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Pisa and drive in the direction of Florence for some laid-back sightseeing. You’ll end your day in Florence, where you’ll stay for 3 nights.

As you explore Pisa’s charming streets, take in the lively atmosphere and get to know the character of the city.

When you’re ready to jump back into the car and say goodbye to Bologna, you’ll hit the road in the direction of Pisa. This drive usually takes around 2 hours 11 min.

Savor the day by heading to Knights' Square, an often recommended public square that draws visitors from near and far. When you're done, continue to Leaning Tower Of Pisa, where you can soak in the remarkable surroundings.

Next, explore Piazza Del Duomo, Pisa, yet another globally renowned place to see in the area. After the public square, make time to go to Pisa Cathedral. This picture-perfect church is well worth the visit.

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

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.

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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

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.

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

Day 12 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!

Make a stop at Ponte Vecchio. This iconic historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Uffizi Gallery located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Della Signoria. Its culturally significant features will captivate you. After the public square, continue your tour of the city with a visit to Galleria Dell'accademia. Visitors usually appreciate the noteworthy features of this art gallery. Next up is David, a highly recommended statue.

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 Florence 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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

Toast to another unforgettable and relaxing road trip adventure 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.

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.

Visiting Piazzale Michelangelo is always a good idea. This extraordinary observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Basilica Of Santa Croce In Florence, a must-see church in the city.

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 Pitti Palace. This captivating palace offers an enriching experience. For a change of pace, head to The Boboli Gardens, where you can take in visually striking features.

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.

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’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 savoring a delicious meal, step into the vibrant nightlife at Gosh*, where the evening is just getting started. In the same way, Antico Caffè Del Moro - Art Bar Firenze offers a unique charm perfect for experiencing the local bar scene in Florence. Quelo Bar 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!

Day 14 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. On this refreshing new day, you’ll travel from Florence and continue your relaxed road trip adventure in Arezzo and Rome. You’ll stay in Rome for 1 night.

Make time for Cathedral Of Santa Maria Del Fiore, an extraordinary church that is worthwhile a visit in the city. Nearby, you’ll find Central Market, enchanting visitors with its picture-perfect appeal. Continue your exploration at Basilica Di Santa Maria Novella, Firenze (fi). This church is one of the city’s most locally renowned spots.

Continue your road trip and head to your next destination, Arezzo. This car ride takes around 1 hour 15 min.

One of our top recommendations for your sightseeing is Piazza Grande. Spend some time admiring the visually striking features of the public square before you continue to your next stop.

You'll be staying in Rome on this laid-back road trip through Italy. You'll stay here for 1 night.

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

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.

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