Two-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Rome to Siena, Bologna, and Florence

Day 2 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!

Savor the day by visiting some of the best places to see in Rome, including a park, a public square, and an archeological site. Start your adventure at Villa Borghese. This astonishing park is a must-visit for travelers looking for a unique holiday experience. Make your way to Spanish Steps located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Piazza Di Spagna. Its history-steeped features will captivate you. After the public square, continue your tour of the city with a visit to Colosseum. Visitors usually appreciate the culturally significant features of this archeological site. Next up is Roman Forum, a highly recommended archeological site.

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.

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.

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

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.

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

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Circus Maximus. This culturally significant archeological site is sure to ignite your curiosity. Next, dive into the culturally significant features of Pantheon, a must-visit monument 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 Navona, a timeless public square. For a change of scene, check out Campo De' Fiori, known for its picture-perfect features. We also recommend visiting Castel Sant'angelo. This castle is a must for anyone looking to experience the city to the fullest.

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.

Experience shopping bliss at Rome as you explore Trastevere. Take a leisurely stroll through unique boutiques and shops, where local treasures are waiting to be found. Don't miss the chance to discover artisan crafts that reflect the fascinating culture of Italy. Beyond shopping, Trastevere offers more options, including unique attractions, key services, and vibrant events.

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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

After dinner, it’s time to fall in love with the amazing nightlife in Rome and unwind at some of the best bars in the city.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

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

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Piazza Del Campo. This astonishing public square is a history-steeped place to see in Siena. Continue your discovery at Siena Cathedral, a grand church with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Fontebranda. This increasingly popular historical landmark offers an eye-catching encounter with Siena. Next, make your way to Basilica Of San Domenico to add another highlight to your day. After that, visit Fortezza Medicea (siena), a worthwhile monument 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 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.

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

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

After enjoying a fulfilling meal, continue your evening at Bar Al Bricco D'oro, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Freud E Squisito offers a welcoming atmosphere for easing into the nightlife. Similarly, Osteria Del Sole provides an excellent environment for a relaxed and enjoyable evening.

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

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 5 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!

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a palace, a monument, a church, a public square and much more! Begin your adventure at Palazzo Re Enzo. This is a curiosity-inducing palace you should not miss. Another must-see is Fountain Of Neptune, Bologna, an up-and-coming monument in Bologna.

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

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.

Treat yourself to a delicious dinner at Bononia Cafè, an excellent option for tonight's dining. Looking for something different? Via Con Me offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Pizzeria La Mela. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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

After your meal, keep the night alive at a bar like Lime Bar, known for its lively atmosphere. Macondo - Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Onda Marina By Night offers an excellent atmosphere for those looking to amp up the evening.

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

Day 7 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!

A blend of family-friendly attractions, picturesque spots, and historic treasures await you in Bologna on today’s itinerary. First up is the beloved monument, Porta Santo Stefano. Afterward, continue to Porta Castiglione, a monument every traveler should visit.

As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Arco Del Meloncello. This frequently visited monument is an essential stop.

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.

Enjoy a lovely dining experience at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia. It’s yet another ideal choice to enhance your time in Bologna tonight.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Aurum stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Senza Nome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Ristretto is also a great option that provides a perfect setting for a relaxing evening.

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

Today's adventure in Bologna promises more breathtaking discoveries and enriching experiences! Begin at Devotional Portico Of St. Luke. This history-steeped monument is a highlight of any visit in the city. Then, enjoy Palazzo Pallavicini, another romantic attraction that never fails to captivate visitors. Next, head over to Chiesa Del Santissimo Salvatore, one of the city’s most locally appreciated attractions, known for its photogenic features.

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

Exploring 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.

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

If you’re not ready to end the night just yet, Bar Piratello offers a perfect venue to relax and savor a drink. Similarly, Bar Carlo is well-suited for those looking to unwind in a social setting. Bar Maurizio 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 9 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Faizan-e-madina Bologna is the perfect place to start. This mosque is one of the most locally appreciated places to visit in Bologna. Next, head to Botanical Garden And Herbarium, a curiosity-inducing botanical garden, known for its romantic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Pinacoteca Nazionale Di Bologna. This heritage-rich art gallery is a highly recommended experience. Nearby, you'll also find San Martino. Visit these for an interesting touch 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 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 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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Brewdog Bar Bologna, where the evening is just getting started. In the same way, Kinotto Bar offers a unique charm perfect for experiencing the local bar scene in Bologna. Mio Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 10 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 home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Two Towers, an interesting monument that is worthwhile a visit in the city. Nearby, you’ll find International Museum And Library Of Music, enchanting visitors with its history-steeped appeal. Continue your exploration at Piazza Santo Stefano. This public square is one of the city’s most beloved 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!

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 delightful dinner at Trattoria da Me, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Botanica Lab Cucina? It's another excellent option with a diverse menu. Consider reserving a table at Café de la Paix as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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

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

Bologna is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Knights' Square, an increasingly popular public square that is worthwhile a visit in the city. Nearby, you’ll find Leaning Tower Of Pisa, enchanting visitors with its culturally significant appeal. Continue your exploration at Piazza Del Duomo, Pisa. This public square is one of the city’s most wondrous spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pisa Cathedral.

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.

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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

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.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

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

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

Ponte Vecchio is must-visit historical landmark and a great starting point for the day. Next, continue your journey to Uffizi Gallery, a top-rated art gallery, located just a leisurely stroll away. Next, head to Piazza Della Signoria, a majestic public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the interesting Galleria Dell'accademia. If you’re looking for more, David is also an interesting 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, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun 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.

On day 13 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, 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 Florence, and meet locals along the way!

One of the most iconic places you can visit today in Florence is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Florence is brimming with adventures. Today’s wonderful stops include an observation deck, a church, a palace, a botanical garden and much more! Begin your sightseeing adventure at the widely recognized Piazzale Michelangelo and allow yourself time to explore. Just a short distance away you'll find your next stop, Basilica Of Santa Croce In Florence, a heritage-rich church that draws visitors from far and near.

Continue your journey to Pitti Palace, one of the city’s most captivating spots that you shouldn’t miss. Another great site to visit is the well-known The Boboli Gardens.

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.

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.

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.

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

Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.

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

Day 14 of your relaxed road trip across the beautiful country of 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!

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Cathedral Of Santa Maria Del Fiore. This enchanting church is a highlight of any visit in the city. Then, enjoy Central Market, another eye-catching attraction that never fails to captivate visitors. Next, head over to Basilica Di Santa Maria Novella, Firenze (fi), one of the city’s most captivating attractions, known for its inviting features.

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

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.

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.

Savor the flavors at Sofitel Roma Villa Borghese, a top pick for dinner tonight. Alternatively, Centro beckons with its unique menu offerings. Also, consider Ristorante Tema. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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

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