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 widely recognized park is a serene place to see in Rome. Continue your discovery at Spanish Steps, a history-steeped 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 timeless public square offers a visually striking 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.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Rome offers a wide selection of experiences for every traveler.

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

Get ready for an unforgettable culinary journey in Rome by reserving a table at La Pergola. Renowned as a 3-star Michelin restaurant, it offers an exceptional mediterranean and contemporary menu. For a different taste experience, head to Il Pagliaccio, recognized for its delicious creative and innovative dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Enoteca La Torre, a local favorite known for its delightful mediterranean and creative cuisine in Rome. Nestled in the heart of the city, this restaurant with 2 Michelin star is an ideal choice for discerning mediterranean and creative foodies seeking culinary excellence.

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

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

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

Day 3 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Start by visiting Circus Maximus, a prime spot to begin your journey. This culturally significant archeological site is sure to impress. Next on your list is Pantheon, another must-visit landmark and wondrous monument renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Navona. This grand public square is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Campo De' Fiori, a spectacular public square. Nearby, you'll also find Castel Sant'angelo, ready to add charm to your journey.

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 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 Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar, a hidden gem nestled in Rome. 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 Rome.

After your meal, keep the night alive at a bar like The Apartment Bar Roma, known for its lively atmosphere. Hotel Hassler Roma is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

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

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.

Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Piazza Del Campo. This widely recognized public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Siena Cathedral, one of the city’s best highlights.

Next, check out Fontebranda, one of the most worthwhile places to see in Siena. This historical landmark is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Basilica Of San Domenico. Wander around and soak in the monumental atmosphere this church offers. Then, head to Fortezza Medicea (siena), a top-rated monument that adds another dimension to your day.

When you’re not exploring beautiful places, you’ll have a relaxed time at Bologna. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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.

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.

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.

Let the evening flow smoothly from dinner to drinks at Bar Al Bricco D'oro, a top-rated bar in the area. For other recommendations, Bar Freud E Squisito provides a perfect setting for rounding out your night with style and great drinks. Likewise, Osteria Del Sole offers a memorable night with diverse drink options and excellent service.

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

Day 6 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!

Bologna is brimming with adventures. Today’s wonderful stops include a palace, a monument, a church, a public square and much more! Begin your sightseeing adventure at the increasingly popular Palazzo Re Enzo and allow yourself time to explore. Just a short distance away you'll find your next stop, Fountain Of Neptune, Bologna, a symbolic monument that draws visitors from far and near.

Continue your journey to Bologna Cathedral, one of the city’s most often recommended spots that you shouldn’t miss. Another great site to visit is the top-rated Piazza Maggiore. When you're finished at the public square, Basilica Of San Domenico awaits your visit. This church is a heritage-rich highlight on today's itinerary.

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.

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.

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.

Let the evening flow smoothly from dinner to drinks at Lime Bar, a top-rated bar in the area. For other recommendations, Macondo - Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Onda Marina By Night offers a memorable night with diverse drink options and excellent service.

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!

Start your adventure at Porta Santo Stefano. This up-and-coming monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Porta Castiglione, a must-see monument in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Arco Del Meloncello. This locally appreciated monument offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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!

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

Don’t miss out on dining at 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.

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.

After enjoying a fulfilling meal, continue your evening at Aurum, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Senza Nome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Ristretto 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 8 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Devotional Portico Of St. Luke. This visually striking monument is sure to ignite your curiosity. Next, dive into the picture-perfect 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.

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.

Enjoy a lovely meal at Pappare' - Bologna, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Mister Coffee Bistrò is another top choice with a popular menu. You could also check for a table at All'Osteria Bottega. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

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

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

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

Day 9 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!

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 an often recommended mosque you should not miss. Another must-see is Botanical Garden And Herbarium, a curiosity-inducing 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 underrated attractions.

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 lovely dining experience at Ristorante Rodrigo, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at CDH Hotel Bologna, 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 Victoria Station. It’s yet another ideal choice to enhance your time in Bologna 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.

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

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!

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most well-known attractions included on the itinerary is Two Towers. This breathtaking monument will help you start your sightseeing on top. Then, take a leisurely stroll to International Museum And Library Of Music and learn what makes this history-steeped museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Piazza Santo Stefano.

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.

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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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.

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

Day 11 of your relaxed road trip across Italy 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.

Set out on a day brimming with fun adventures, scenic views, and picturesque spots. Start at the increasingly popular Knights' Square, a culturally significant public square in Bologna. Next, go to Leaning Tower Of Pisa.

After visiting Knights' Square and Leaning Tower Of Pisa, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Duomo, Pisa. This breathtaking public square offers a unique experience. Pisa Cathedral is another noteworthy attraction worthwhile a visit.

You’ll be staying at the incredible city of Florence in this laid-back road trip in 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.

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative and mediterranean cuisine. Another highly-recommended place to eat in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious italian contemporary and international menu.

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

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 12 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

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 instagrammable 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 widely recognized enchanting spots of interest. After exploring the public square, visit the well-known Galleria Dell'accademia. Not far away, you'll also find David.

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!

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.

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.

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

Day 13 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!

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazzale Michelangelo is the perfect place to start. This observation deck is one of the most top-rated places to visit in Florence. Next, head to Basilica Of Santa Croce In Florence, an interesting church, known for its respected 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 Pitti Palace. This romantic palace is a highly recommended experience. Nearby, you'll also find The Boboli Gardens. Visit these for an interesting touch to your journey.

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 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.

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

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

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.

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.

On day 14 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. 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. Cathedral Of Santa Maria Del Fiore is the first of them. Spend some time admiring this enchanting church before continuing your journey. Central Market is your next stop. This popular food market is one of the best-rated sights in Florence.

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 Basilica Di Santa Maria Novella, Firenze (fi). This majestic church is a sight to behold. To round off your sightseeing experience, visit Piazza Grande.

In the city of Rome, 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.

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.

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.

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.

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.