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!

Catch Villa Borghese before the crowds roll in. This masterful park is sure to ignite your curiosity. Next, dive into the romantic features of Spanish Steps, a must-visit public square 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 Di Spagna, a wondrous public square. For a change of scene, check out Colosseum, known for its breathtaking features. We also recommend visiting Roman Forum. This archeological site 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!

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.

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.

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

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

Day 3 of your relaxed road trip through Italy means 24 hours of making the best memories in 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!

No visit to Rome is complete without Circus Maximus. This notable archeological site is one of the top attractions in the city. Proceed to Pantheon, 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 Navona. This wondrous public square is a traveler-favorite. Not far away, you’ll find Campo De' Fiori, another key site on your sightseeing itinerary. Castel Sant'angelo 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.

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

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 lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Rome tonight.

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.

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.

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

Day 5 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!

Let Piazza Del Campo set the tone for the day. Spend some time admiring this romantic public square before continuing your journey. Siena Cathedral is your next stop. This well-known church is one of the best-rated sights in Siena.

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 Fontebranda. This photogenic historical landmark is a sight to behold. To round off your sightseeing experience, visit Basilica Of San Domenico and Fortezza Medicea (siena).

After a day of exploration, relax at one of the top hotels or accommodations in Bologna. 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 Bologna.

Experience a symphony of flavors at Ahimè in Bologna by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Ahimè delights its guests with its exceptional variety of meals showcasing delicious country cooking cuisine. For a palate-pleasing alternative, make sure to dine at I Portici, acclaimed for its delectable creative and contemporary specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Trattoria di Via Serra, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for emilian cuisine in the city.

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.

Explore the vibrant nightlife at Bar Al Bricco D'oro after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Freud E Squisito for a great selection of flavorful drinks and a charming setting. Furthermore, Osteria Del Sole is perfect for those looking to extend their night with a touch of local flavor.

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, a frequently visited monument, located just a leisurely stroll away. Next, head to Bologna Cathedral, a breathtaking 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 astonishing Piazza Maggiore. If you’re looking for more, Basilica Of San Domenico is also a locally appreciated attraction that is worthwhile a visit.

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.

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.

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.

If you’re not ready to end the night just yet, Lime Bar offers a perfect venue to relax and savor a drink. Similarly, Macondo - Cocktail Bar is well-suited for those looking to unwind in a social setting. Bar Onda Marina By Night is another excellent spot to enjoy a nightcap after a delightful meal.

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!

To truly experience Bologna, make sure to drop by Porta Santo Stefano. This up-and-coming monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Porta Castiglione, one of the city’s best highlights.

Next, check out Arco Del Meloncello, one of the most increasingly popular places to see in Bologna. This monument is a favorite among locals and travelers alike.

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

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.

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 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!

Whatever your travel style is, Devotional Portico Of St. Luke is an essential stop in Bologna. This underrated monument provides an insightful glimpse into the city's identity. Next, discover Palazzo Pallavicini, an eye-catching palace, promising a delightful encounter.

Continue your sightseeing with a visit to Chiesa Del Santissimo Salvatore, a locally appreciated church.

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!

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.

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.

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

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

Raise your glass and relax after another big day of your leisurely paced road trip 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 makes a great addition to your morning plans. This curiosity-inducing mosque is a monumental place to see in Bologna. Continue your discovery at Botanical Garden And Herbarium, an eye-catching botanical garden with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pinacoteca Nazionale Di Bologna. This underrated art gallery offers a visually striking encounter with Bologna. Next, make your way to San Martino to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

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.

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.

Treat yourself to a delightful dinner at Ristorante Rodrigo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try CDH Hotel Bologna? It's another excellent option with a diverse menu. Consider reserving a table at Victoria Station as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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.

To truly maximize your evening out, consider visiting Brewdog Bar Bologna after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Kinotto Bar, another bar with an inviting ambiance. Similarly, Mio Bar 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!

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.

Let Two Towers set the tone for the day. Spend some time admiring this historic monument before continuing your journey. International Museum And Library Of Music is your next stop. This up-and-coming museum 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 Piazza Santo Stefano. This visually striking public square is a sight to behold.

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 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 a delicious dinner at Trattoria da Me, an excellent option for tonight's dining. Looking for something different? Botanica Lab Cucina offers a tantalizing alternative with its diverse menu. And don’t miss Café de la Paix. Known for great service, it’s a fantastic choice for tonight in Bologna.

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

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

Day 11 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Pisa. By evening, drive toward the Florence, where you’ll stay at a top-rated hotel of your choice for 3 nights.

Knights' Square makes a great addition to your morning plans. This curiosity-inducing public square is a picture-perfect place to see in Bologna. Continue your discovery at Leaning Tower Of Pisa, a picture-perfect monument with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Duomo, Pisa. This wondrous public square offers an UNESCO world heritage-designated encounter with Bologna. Next, make your way to Pisa Cathedral to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

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.

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.

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

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Cherish every minute of your relaxed road trip vacation across 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!

Ponte Vecchio brings Florence's character to life. This majestic historical landmark is a highlight of any visit in the city. Then, enjoy Uffizi Gallery, another standout attraction that never fails to captivate visitors. Next, head over to Piazza Della Signoria, one of the city’s most top-rated attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Galleria Dell'accademia. This photogenic art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to visit David, a popular statue, and take a stroll around the area.

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 Florence.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery 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 13 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

A top thing to do today is to explore Oltrarno, a must-see neighborhood in Florence. It's the perfect starting point for touring the top attractions in the area.

Start your day at Piazzale Michelangelo. This history-steeped observation deck is an astonishing place to see in Florence. Then, wander over to Basilica Of Santa Croce In Florence. If instagrammable sites excite you, this church will be right up your alley. Nearby, you’ll also find Pitti Palace. This visually striking palace is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, The Boboli Gardens is a well-known spot in the city that will captivate you with its unique charm.

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!

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

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.

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 self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Florence and end it in Rome. You’ll stay in Rome for 1 night. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Cathedral Of Santa Maria Del Fiore is an ideal stop early in the day. This famous church is a must-visit in the city. When you’re ready for your next discovery, continue to Central Market, which may be one of the most eye-catching places you will experience today.

One of the best things about exploring Florence 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 Basilica Di Santa Maria Novella, Firenze (fi), a notable church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Grande.

In Rome, 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.

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.

Make sure to reserve a table at Sofitel Roma Villa Borghese, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Centro, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Tema, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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