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!

Today’s route brings fun adventures, romantic experiences, and natural wonders. The first attraction of today is Villa Borghese. This extraordinary park is a mesmerizing place to see in Rome. Continue your discovery at Spanish Steps, a visually striking public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Di Spagna. This globally renowned public square offers an enchanting encounter with Rome. Next, make your way to Colosseum to add another highlight to your day. After that, visit Roman Forum, a wondrous archeological site that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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!

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.

Dive into a culinary adventure like no other in Rome by booking a table at La Pergola. This popular restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another culinary dining option, venture to Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Enoteca La Torre, a top local restaurant known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it promises an exceptional dining experience not to be missed.

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

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

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

Get ready for a day filled with fun adventures, scenic views, and photo-friendly spots in the charming city of Rome. Your adventure starts at Circus Maximus, a well-known local hot spot. Another notable attraction to explore is Pantheon. This globally renowned monument is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Navona. This history-steeped public square offers a fascinating experience that many visitors find memorable. Campo De' Fiori is also worth visiting, along with Castel Sant'angelo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

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.

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

Cherish every minute of your relaxed road trip vacation across 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.

Today, you'll explore some of the most beautiful places in Siena, including a public square, a church, a historical landmark, a monument and much more! Start your day with a visit to Piazza Del Campo. This extraordinary public square is a must-visit in the city. When you’re ready for your next discovery, continue to Siena Cathedral, which may be one of the most enchanting places you will experience today.

One of the best things about exploring Siena 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 Fontebranda, a worthwhile historical landmark in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of San Domenico and Fortezza Medicea (siena).

Continue your laid-back road trip exploration of the best attractions in Italy at Bologna. 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 Bologna.

Discover the culinary delights of Bologna by securing a reservation at Ahimè. Esteemed for its a Bib Gourmand award, this restaurant offers a remarkable selection of country cooking cuisine. For an alternative dining experience, try I Portici, renowned for its delicious creative and contemporary dishes. This esteemed 1-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Trattoria di Via Serra, a highly recommended local eatery celebrated for its mouthwatering emilian menu. With its Bib Gourmand recognition, it offers an unforgettable dining adventure.

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.

Round off your dining experience by visiting Bar Al Bricco D'oro, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Freud E Squisito, a bar catering to every mood and preference. Osteria Del Sole likewise offers a unique atmosphere, perfect for a memorable night out.

Soak in the unique atmosphere of Bologna as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday 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 beloved 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 extraordinary Piazza Maggiore. If you’re looking for more, Basilica Of San Domenico is also an up-and-coming 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.

Dine in style at Bononia Cafè, a top recommendation for dinner tonight. Or, for a change of pace, Via Con Me boasts a menu that's sure to impress. Also, be sure to check out Trattoria Pizzeria La Mela. Known as a local hotspot, it’s a great choice 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.

Extend your evening after a delightful meal by visiting Lime Bar, which offers the perfect atmosphere for a night out. Moreover, Macondo - Cocktail Bar is another popular option for a drink or two. Likewise, Bar Onda Marina By Night 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!

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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Porta Santo Stefano. This beloved monument provides an insightful glimpse into the city's identity. Next, discover Porta Castiglione, an instagrammable monument, promising a delightful encounter.

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

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 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 Va Mo Là, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Trattoria dal Biassanot, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Enoteca da Lucia. With a reputation for consistently satisfying customers, it’s an excellent 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.

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

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!

Savor the day by visiting some of the best places to see in Bologna, including a monument, a palace, and a church. Start your adventure at Devotional Portico Of St. Luke. This locally appreciated monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Palazzo Pallavicini located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Chiesa Del Santissimo Salvatore. Its heritage-rich features will captivate you.

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!

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 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.

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

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

Today, you'll explore some of the most beautiful places in Bologna, including a mosque, a botanical garden, an art gallery, a church and much more! Start your day with a visit to Faizan-e-madina Bologna. This up-and-coming mosque is a must-visit in the city. When you’re ready for your next discovery, continue to Botanical Garden And Herbarium, which may be one of the most peaceful places you will experience today.

One of the best things about exploring Bologna on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Pinacoteca Nazionale Di Bologna, a curiosity-inducing art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for San Martino.

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.

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.

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

Soak in the unique atmosphere of Bologna as you commemorate this day of your relaxed road trip through Italy 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!

Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and picturesque spots. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Two Towers is the first of them. Spend some time admiring this picture-perfect monument before continuing your journey. International Museum And Library Of Music is your next stop. This underrated 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 romantic public square is a sight to behold.

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 Bologna, 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 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.

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

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

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

Savor the day by visiting some of the best places to see in Bologna, including a public square, a monument, and a church. Start your adventure at Knights' Square. This underrated public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Leaning Tower Of Pisa located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Piazza Del Duomo, Pisa. Its UNESCO world heritage-listed features will captivate you. After the public square, continue your tour of the city with a visit to Pisa Cathedral. Visitors usually appreciate the picture-perfect features of this church.

In the city of Florence, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Florence. The bars in Florence make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Ponte Vecchio, a world-famous historical landmark in the city. Then, head to Uffizi Gallery and soak in the ambiance of this historic art gallery.

There are many interesting places to see in Florence, and when you are ready for more, go to Piazza Della Signoria. This is one of the city’s most extraordinary visually striking spots of interest. After exploring the public square, visit the interesting Galleria Dell'accademia. Not far away, you'll also find David.

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 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.

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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience 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 one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Start by visiting Piazzale Michelangelo, a prime spot to begin your journey. This symbolic observation deck is sure to impress. Next on your list is Basilica Of Santa Croce In Florence, another must-visit landmark and interesting church renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Pitti Palace. This romantic palace is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting The Boboli Gardens, a notable 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 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 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.

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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

Day 14 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Florence. By the end of the day, you’ll drive in the direction of the city of Rome, where you’ll stay at a top-rated hotel of your choice for 1 night.

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Florence. Your adventure starts at Cathedral Of Santa Maria Del Fiore, a top-rated local hot spot. Another notable attraction to explore is Central Market. This notable food market is known for its UNESCO world heritage-designated 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 Basilica Di Santa Maria Novella, Firenze (fi). This grand church offers a fascinating experience that many visitors find memorable. Piazza Grande is also worth visiting.

You’ll be staying at the incredible city of Rome in this laid-back road trip in Italy. You'll stay here for 1 night.

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.

Don’t miss out on dining 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.

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

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.