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!

Whatever your travel style is, Villa Borghese is an essential stop in Rome. This extraordinary park provides an insightful glimpse into the city's identity. Next, discover Spanish Steps, an enchanting public square, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Di Spagna, a globally renowned public square. When you’re done, don’t forget to make a stop at the globally renowned Colosseum. Round off your day at Roman Forum, another gem in Rome with picture-perfect features to discover.

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!

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.

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.

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.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

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

Circus Maximus is an ideal stop early in the day. This interesting archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Pantheon, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Rome 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 Navona, a globally renowned public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Campo De' Fiori and Castel Sant'angelo.

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 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 Rome, 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 Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

Explore the vibrant nightlife at The Apartment Bar Roma after your meal, a hub for lively evenings and memorable moments. Or, head to Hotel Hassler Roma for a great selection of flavorful drinks and a charming setting.

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

Day 5 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Siena and drive in the direction of Bologna for some laid-back sightseeing. You’ll end your day in Bologna, where you’ll stay for 6 nights.

No visit to Siena is complete without Piazza Del Campo. This impressive public square is one of the top attractions in the city. Proceed to Siena Cathedral, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Fontebranda. This curiosity-inducing historical landmark is a traveler-favorite. Not far away, you’ll find Basilica Of San Domenico, another key site on your sightseeing itinerary. Fortezza Medicea (siena) is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

In Bologna, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

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.

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

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.

Cap off your dinner by heading to Bar Al Bricco D'oro, ideal for a leisurely evening with a drink in hand. Bar Freud E Squisito is another bar that offers an enjoyable setting. Similarly, Osteria Del Sole is also a popular place to go on a night out, perfect for relaxing and socializing.

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.

Day 6 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Enjoy all that Palazzo Re Enzo has to offer. This is a curiosity-inducing palace you should not miss. Another must-see is Fountain Of Neptune, Bologna, a locally appreciated monument in Bologna.

When you’re ready for the next sight, head to Bologna Cathedral. From there, take a leisurely stroll to Piazza Maggiore, another of the city’s famous attractions. We recommend continuing your self-guided tour at Basilica Of San Domenico, a photogenic place of interest in the city.

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.

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 Bononia Cafè, 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 Via Con Me, 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 Trattoria Pizzeria La Mela, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Lime Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Macondo - Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Bar Onda Marina By Night 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!

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!

Bologna is brimming with adventures.

Make time for Porta Santo Stefano, a worthwhile monument that is worthwhile a visit in the city. Nearby, you’ll find Porta Castiglione, enchanting visitors with its standout appeal. Continue your exploration at Arco Del Meloncello. This monument is one of the city’s most beloved spots.

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 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.

Treat yourself to a delicious dinner at Va Mo Là, an excellent option for tonight's dining. Looking for something different? Trattoria dal Biassanot offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Enoteca da Lucia. Known for great service, it’s a fantastic choice for tonight in Bologna.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Aurum, known for its inviting atmosphere. Bar Senza Nome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Ristretto provides a great setting to enjoy the night away.

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!

Devotional Portico Of St. Luke leaves a lasting impression. This monument is one of the most underrated places to visit in Bologna. Next, head to Palazzo Pallavicini, an increasingly popular palace, known for its romantic 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 Chiesa Del Santissimo Salvatore. This culturally significant church is a highly recommended experience.

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.

Make sure to reserve a table at Pappare' - Bologna, 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 Mister Coffee Bistrò, 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 All'Osteria Bottega, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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.

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.

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

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

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.

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 Ristorante Rodrigo, a highly-rated dining destination in Bologna. If you're eager to try something different, consider CDH Hotel Bologna, another top spot with a tantalizing menu. You might also want to secure a reservation at Victoria Station. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

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

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.

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

No visit to Bologna is complete without Two Towers. This popular monument is one of the top attractions in the city. Proceed to International Museum And Library Of Music, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Santo Stefano. This increasingly popular public square is a traveler-favorite.

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.

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.

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.

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.

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 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.

Continue your road trip and head to your next destination, Pisa. This car ride takes around 2 hours 11 min.

Spend your afternoon discovering Knights' Square, an up-and-coming public square known for its culturally significant features. Next, continue your sightseeing at Leaning Tower Of Pisa, a world-famous monument.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Del Duomo, Pisa and uncover the details of this stunning public square. Make sure to also explore Pisa Cathedral, an up-and-coming church.

You'll be staying in Florence on this laid-back road trip through Italy. You'll stay here for 3 nights.

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.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

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

Your adventure in Florence is only getting started when you visit Ponte Vecchio, a timeless local hot spot. Another notable attraction to explore is Uffizi Gallery. This spectacular art gallery is known for its visually striking appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Della Signoria. This culturally significant public square offers a fascinating experience that many visitors find memorable. Galleria Dell'accademia is also worth visiting, along with David. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and toast to another unforgettable, laid-back 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.

Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Make sure to visit Oltrarno, a popular neighborhood in Florence. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Make a stop at Piazzale Michelangelo. This widely recognized observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Of Santa Croce In Florence located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Pitti Palace. Its romantic features will captivate you. After the palace, continue your tour of the city with a visit to The Boboli Gardens. Visitors usually appreciate the history-steeped features of this botanical garden.

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!

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 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.

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 your meal, keep the night alive at a bar like Gosh*, known for its lively atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Quelo Bar offers an excellent atmosphere for those looking to amp up the 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.

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.

One of the most astonishing attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This history-steeped church will help you start your sightseeing on top. Then, take a leisurely stroll to Central Market and learn what makes this instagrammable food market unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the well-known Basilica Di Santa Maria Novella, Firenze (fi).

Set your GPS to Arezzo and hit the road. Expect a journey of approximately 1 hour 15 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Arezzo beckons with new experiences!

Set out on a self-guided sightseeing tour at Piazza Grande and explore the romantic features.

When you’re not exploring beautiful places, you can relax in Rome. 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 Rome, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a delicious meal at Sofitel Roma Villa Borghese, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Centro, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s a perfect 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.

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