Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Siena, Rome, and Florence

Day 2 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 an awe-inspiring, an instagrammable, a historic, a majestic, a charming, and a culturally significant await you in Bologna on today’s itinerary. First up is the popular monument, Two Towers. It's a standout spot that offers a memorable visit. Afterward, continue to International Museum And Library Of Music. A visit to this museum is an enriching experience for all.

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 Piazza Santo Stefano. This often recommended public square is an essential stop that should not be missed. Following that, head to Piazza Maggiore, another must-visit site that will enhance your experience.

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 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.

Get ready for an unforgettable culinary journey in Bologna by reserving a table at Ahimè. Renowned as a Bib Gourmand restaurant, it offers an exceptional country cooking menu. For a different taste experience, head to I Portici, recognized for its delicious creative and contemporary dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Trattoria di Via Serra, a local favorite known for its delightful emilian cuisine in Bologna. Nestled in the heart of the city, this Bib Gourmand awardee is an ideal choice for discerning emilian foodies seeking culinary excellence.

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.

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

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

Day 3 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 Palazzo Del Podestà, Bologna. This photogenic palace is a highlight of any visit in the city. Then, enjoy Fountain Of Neptune, Bologna, another photogenic attraction that never fails to captivate visitors. Next, head over to Palazzo Re Enzo, one of the city’s most worthwhile attractions, known for its standout 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 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.

Make sure to reserve a table at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Keep the evening going at Aurum, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Senza Nome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Ristretto, 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 4 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Siena for 1 night.

Today’s agenda in Bologna includes a church, a monument, and a palace. Chiesa Del Santissimo Salvatore is must-visit church and a great starting point for the day. Next, continue your journey to Tombs Of The Glossators Of Bologna, an increasingly popular monument, located just a leisurely stroll away. Next, head to Palazzo Pallavicini, a history-steeped palace, also available for your discovery today.

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

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

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

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

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

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, 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 Rome, and meet locals along the way!

Today’s itinerary in Rome covers several incredible sights, including a castle, a public square, and a monument. Start your adventure at Castel Sant'angelo. This famous castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Campo De' Fiori, a must-see public square 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 Piazza Navona. This wondrous public square offers an enriching experience. For a change of pace, head to Pantheon, where you can take in its culturally significant features. Conclude your self-guided sightseeing tour with a visit to Trevi Fountain. This noteworthy monument offers a fulfilling end to a perfect day.

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 Rome, explore the city like a local by trying out the best restaurants in the area.

Make sure to book a table at RomAntica, a popular restaurant in Rome. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Rome at Coso Ristorante, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is DEROMA - Farine Romane. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Rome tonight.

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.

Toast to another unforgettable and relaxing road trip adventure in Italy!

Day 7 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, you'll explore some of the most beautiful places in Rome, including an archeological site and a monument. Start your day with a visit to Largo Di Torre Argentina. This locally renowned archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Altare Della Patria, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Rome 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 Roman Forum, one of the city’s most globally renowned archeological site. If you’re up for more discoveries, don’t forget to reserve some time for Colosseum and Circus Maximus.

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.

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.

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.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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

Day 8 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Today’s agenda in Rome includes a sport complex, a park, and a public square. Foro Italico is must-visit sports complex and a great starting point for the day. Next, continue your journey to Villa Borghese, an extraordinary park, located just a leisurely stroll away. Next, head to Piazza Del Popolo, a mesmerizing 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 Rome. If you’re looking for more, Piazza Di Spagna is also a wondrous attraction that is worthwhile a visit. Lastly, don’t miss Spanish Steps, an extraordinary gem to see in the city.

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.

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

Enjoy a delicious meal at Sofitel Roma Villa Borghese, a highly-rated dining destination in Rome. If you're eager to try something different, consider Centro, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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

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

Day 10 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the town of Orvieto and drive in the direction of the village of Orvieto for some laid-back sightseeing. You’ll end your day in the city of Florence, where you’ll stay for 3 nights.

Set your GPS to Orvieto and hit the road. Expect a journey of approximately 1 hour 38 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Orvieto beckons with new experiences!

Orvieto Cathedral is a popular church we recommend making time to visit today. Discover its enchanting features before continuing your self-guided tour to Museo Dell'opera Del Duomo, a photogenic museum that’s well-regarded in the area.

After soaking in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Orvieto. Expect your car journey to take a minimum of 1 hour 38 min. When you arrive in Orvieto, it's time to take a break from the road.

Your self-guided tour starts at Well Of St. Patrick, a captivating monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

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

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.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another culinary dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

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.

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

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

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, 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 Florence, and meet locals along the way!

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most astonishing attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This history-steeped church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Della Repubblica and learn what makes this visually striking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the famous Piazza Della Signoria. After exploring the public square, head to Uffizi Gallery. This astonishing art gallery is a highlight in Florence. Lastly, don’t forget to check out the wondrous Ponte Vecchio. Enjoy exploring this incredible historical landmark at your own pace.

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.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

Soak in the unique atmosphere of Florence 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 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!

Start by visiting Basilica Di Santa Maria Novella, Firenze (fi), a prime spot to begin your journey. This inviting church is sure to impress. Next on your list is Central Market, another must-visit landmark and locally renowned food market renowned for its visually striking features.

While exploring and sightseeing, take time to savor the ambiance of Florence by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Galleria Dell'accademia. This detailed art gallery is a remarkable attraction that offers a unique experience. David also adds charm to your journey, and Piazzale Michelangelo wraps up your day with its culturally significant appeal.

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 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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar 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!

On day 13 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 adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Basilica Of Santa Croce In Florence. This instagrammable church is a highlight of any visit in the city.

As you’ve unraveled the marvels of Florence, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 1 hour 23 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Savor the rest of your day by heading to Leaning Tower Of Pisa, a world-famous monument that draws visitors from near and far. When you're done, continue on to Piazza Del Duomo, Pisa, where you can soak in the UNESCO world heritage-designated surroundings.

In the city of Bologna, 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 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.

Have a fantastic dining experience at Pappare' - Bologna, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Mister Coffee Bistrò offers an enticing alternative with its varied menu. Additionally, All'Osteria Bottega is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

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.

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

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!