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!

Discover a day packed with family-friendly attractions, romantic experiences, and natural wonders in Rome. Begin your sightseeing with Villa Borghese. This spectacular 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.

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.

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.

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 Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino 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 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!

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and photo-friendly spots. 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. Circus Maximus is the first of them. Spend some time admiring this picture-perfect archeological site before continuing your journey. Pantheon is your next stop. This timeless 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.

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.

Visit Trastevere in Rome for an unforgettable shopping experience. Browse unique boutiques and stores, each offering delightful surprises. Find unique souvenirs or items to take home, including artisan crafts. After shopping, explore what Trastevere has to offer, including attractions, essential services, and vibrant community activities.

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 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 gains consistently high praises from customers, it’s an ideal choice 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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

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

Day 5 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Bologna for 6 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Siena is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Piazza Del Campo, a famous public square that is worthwhile a visit in the city. Nearby, you’ll find Siena Cathedral, enchanting visitors with its visually striking appeal. Continue your exploration at Fontebranda. This historical landmark is one of the city’s most increasingly popular spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Basilica Of San Domenico. After exploring the church, head to the locally appreciated Fortezza Medicea (siena).

You’ll be staying at the incredible city of Bologna in this laid-back road trip in Italy. You'll stay here for 6 nights.

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.

Begin your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, another top-rated place in the area.

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

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

Today’s agenda in Bologna includes a palace, a monument, a church, a public square and much more! Palazzo Re Enzo is must-visit palace and a great starting point for the day. Next, continue your journey to Fountain Of Neptune, Bologna, a frequently visited 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 impressive Piazza Maggiore. If you’re looking for more, Basilica Of San Domenico is also an intriguing attraction that is worthwhile a visit.

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

Exploring 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 delightful dinner at Bononia Cafè, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Via Con Me? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Pizzeria La Mela as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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

Round off your dining experience by visiting Lime Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Macondo - Cocktail Bar, a bar catering to every mood and preference. Bar Onda Marina By Night likewise offers a unique atmosphere, perfect for a memorable night out.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Bologna!

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

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Bologna to find the best options for you!

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.

Dine in style at Va Mo Là, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria dal Biassanot boasts a menu that's sure to impress. Also, be sure to check out Ristorante Enoteca da Lucia. Known as a local hotspot, it’s a great choice 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 Aurum after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Senza Nome, another bar with an inviting ambiance. Similarly, Caffè Ristretto 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 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!

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Devotional Portico Of St. Luke. This inviting monument is sure to ignite your curiosity. Next, dive into the instagrammable features of Palazzo Pallavicini, a must-visit palace 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 Chiesa Del Santissimo Salvatore, an intriguing church.

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.

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.

Treat yourself to a delicious dinner at Pappare' - Bologna, an excellent option for tonight's dining. Looking for something different? Mister Coffee Bistrò offers a tantalizing alternative with its diverse menu. And don’t miss All'Osteria Bottega. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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

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

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

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

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a mosque, a botanical garden, an art gallery, a church and much more! Begin your adventure at Faizan-e-madina Bologna. This is a worthwhile mosque you should not miss. Another must-see is Botanical Garden And Herbarium, a beloved botanical garden in Bologna.

When you’re ready for the next sight, head to Pinacoteca Nazionale Di Bologna. From there, take a leisurely stroll to San Martino, another of the city’s increasingly popular attractions.

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.

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.

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

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across 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!

Get ready for a day filled with fun adventures, breathtaking views, and picturesque spots in the charming city of Bologna. Your adventure starts at Two Towers, an interesting local hot spot. Another notable attraction to explore is International Museum And Library Of Music. This up-and-coming museum is known for its picture-perfect 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 grand public square offers a fascinating experience that many visitors find memorable.

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

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.

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

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

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

Day 11 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Florence for 3 nights.

Bologna is brimming with adventures. Today’s wonderful stops include a public square, a monument, and a church. Begin your sightseeing adventure at the often recommended Knights' Square and allow yourself time to explore. Just a short distance away you'll find your next stop, Leaning Tower Of Pisa, a breathtaking monument that draws visitors from far and near.

Continue your journey to Piazza Del Duomo, Pisa, one of the city’s most globally renowned spots that you shouldn’t miss. Another great site to visit is the beloved Pisa Cathedral.

Continue your laid-back road trip exploration of the best attractions in Italy at Florence. Select from top hotels and accommodations in the city to recharge and rejuvenate.

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.

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.

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.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the world-famous Ponte Vecchio, a romantic historical landmark in Florence. Next, go to Uffizi Gallery.

After visiting Ponte Vecchio and Uffizi Gallery, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Della Signoria. This history-steeped public square offers a unique experience. Galleria Dell'accademia is another noteworthy attraction worthwhile a visit.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Florence. There are so many fun and eye-opening activities to try out in Florence that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Florence to find the best options for you!

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.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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.

Oltrarno is a fantastic place you can explore today in Florence. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Florence-way-of-life and visit all the nearby sights.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Piazzale Michelangelo. This spectacular observation deck is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of Santa Croce In Florence, one of the city’s best highlights.

Next, check out Pitti Palace, one of the most locally renowned places to see in Florence. This palace is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, The Boboli Gardens. Wander around and soak in the history-steeped atmosphere this botanical garden offers.

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.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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

Day 14 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Florence and drive in the direction of the city of Arezzo for some laid-back sightseeing. You’ll end your day in the city of Rome, where you’ll stay for 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, a food market, and a public square. Begin your adventure at Cathedral Of Santa Maria Del Fiore. This is a spectacular church you should not miss. Another must-see is Central Market, a well-known food market in Florence.

When you’re ready for the next sight, head to Basilica Di Santa Maria Novella, Firenze (fi). From there, take a leisurely stroll to Piazza Grande, another of the city’s well-known attractions.

After a day of exploration, relax at one of the top hotels or accommodations in Rome. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

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.

Treat yourself to a wonderful meal at Sofitel Roma Villa Borghese, a top-rated dining spot in Rome. If you're in the mood for something new, try Centro, another premier location with a delectable menu. You might also want to book a table at Ristorante Tema. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

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

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