14-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to San Gimignano, Panzano in Chianti, Perugia, Orvieto, Rome, and Naples

Day 2 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Set aside time today to explore Oltrarno, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Of Santa Croce In Florence. This culturally significant church is sure to ignite your curiosity. Next, dive into the symbolic features of Piazza Della Signoria, a must-visit public square 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 Uffizi Gallery, an astonishing art gallery. For a change of scene, check out Ponte Vecchio, known for its visually striking features. We also recommend visiting The Boboli Gardens. This botanical garden is a must for anyone looking to experience the city to the fullest.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

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.

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.

Take some time to reflect on your day and savor another beautiful night in Italy.

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazza Del Duomo, Pisa is the perfect place to start. This public square is one of the most timeless places to visit in Florence. Next, head to Leaning Tower Of Pisa, an iconic monument, known for its detailed 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 Piazza Dell'anfiteatro. This romantic public square is a highly recommended experience. Nearby, you'll also find Guinigi Tower and Mura Di Lucca. Visit these for an interesting touch to your journey.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a delicious meal at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

Get a good night's sleep and look forward to another great day on the road in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in San Gimignano, where you’ll be staying for 1 night.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming city of Florence. Your adventure starts at Siena Cathedral, an interesting local hot spot. Another notable attraction to explore is Facciatone. This up-and-coming observation deck is known for its grand 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 Piazza Del Campo. This romantic public square offers a fascinating experience that many visitors find memorable. Tower Of Mangia is also worth visiting, along with Porta San Giovanni. These standout landmarks offer unique experiences that add to the day’s enjoyment.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in San Gimignano. San Gimignano offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of San Gimignano's most popular restaurants, and connect with friendly locals for an authentic adventure.

Say good night to San Gimignano and look forward to another great day of your road trip in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 3 stops and experience some of the highlights of San Gimignano, Volterra, and Castellina in Chianti. At the end of the day, you will enjoy the comforts of a top-rated hotel in Panzano in Chianti, which will be your home away from home for 2 nights.

San Gimignano is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Piazza Del Duomo, a beloved public square that is worthwhile a visit in the village. Nearby, you’ll find Parco Della Rocca, enchanting visitors with its stunning appeal. Continue your exploration at Etruscan Museum "mario Guarnacci". This museum is one of the village’s most underrated spots.

Enjoy the freedom of exploring San Gimignano at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Porta A Selci. After exploring the monument, head to the curiosity-inducing Poggio Amorelli.

When you’re done exploring for the day, you’ll drive to your hotel in Panzano in Chianti. Check in and spend some time relaxing before you head out to tour the village.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Panzano in Chianti. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Head back to your accommodation in Panzano in Chianti and get some rest in preparation for another magical day of your road trip in Italy!

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Panzano in Chianti for your remaining 1 night in the village later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in San Regolo and Castellina in Chianti.

Today’s agenda in Panzano in Chianti includes a castle and an archeological site. Castello Di Brolio is must-visit castle and a great starting point for the day. Next, continue your journey to Tumulo Di Montecalvario, an underrated archeological site, located just a leisurely stroll away. Next, head to Rocca Di Castellina In Chianti, a history-steeped castle, also available for your discovery today.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Panzano in Chianti.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Panzano in Chianti. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Say good night to Panzano in Chianti and look forward to another great day of your road trip in Italy!

On day 7 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Savor the day by visiting some of the best places to see in Panzano in Chianti, including a church, a castle, a cave system, a public square, a monument and much more! Start your adventure at Basilica Of San Francesco D'assisi. This locally renowned church is a must-visit for travelers looking for a unique holiday experience. Make your way to Rocca Maggiore located in Panzano in Chianti for another exciting encounter.

Next, immerse yourself in the setting of Perugia Sotterranea Accesso. Its heritage-rich features will captivate you. After the cave system, continue your tour of the town with a visit to Perugia Cathedral. Visitors usually appreciate the heritage-rich features of this church. Next up is Piazza Iv Novembre, a highly recommended public square. For a change of pace, head to The Fontana Maggiore. As one of the most worthwhile attractions in Panzano in Chianti, this monument is the perfect place to end your self-guided sightseeing tour.

At the end of the day, you will drive to Perugia, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Ristorante Settimo Sigillo, a popular restaurant in Perugia. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Perugia at Caffè Baglioni, 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 Bar Pellas. It’s yet another ideal choice to enhance your time in Perugia tonight.

Continue your evening by exploring the vibrant nightlife scene at Tommi Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Valentina, a bar that offers unique local touches. Likewise, Caffe Dal Perugino provides an excellent alternative for a fun evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Perugia and Orvieto, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Orvieto. You’ll stay here for 1 night.

Start by visiting Carducci Gardens, a prime spot to begin your journey. This gorgeous park is sure to impress. Next on your list is Orvieto Cathedral, another must-visit landmark and notable church renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of Perugia by sampling some local delicacies. When you’re ready for more sightseeing, head to Orvieto Underground. This respected cave system is an essential place to visit for anyone looking for the full Perugia experience. We also recommend visiting Pozzo Della Cava, an up-and-coming cave.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Orvieto. Orvieto offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you explore more of Orvieto, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

After your meal, keep the night alive at a bar like Bar Duomo, known for its lively atmosphere.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 2 nights here for some well-deserved relaxation.

Today, you'll explore some of the most beautiful places in Orvieto, including an archeological site, a monument, and a public square. Start your day with a visit to Colosseum. This iconic archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Roman Forum, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Orvieto 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 Trevi Fountain, a timeless monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pantheon and Piazza Navona.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and spend some time relaxing before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

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

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

On day 10 of your road trip, you’ll start and end your day in Rome, where you'll stay for 1 night more.

A visit to Trastevere in Vatican City 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. Don’t forget to check out Via del Corso as well, a street that adds another layer to your exploration.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Vatican Museums.

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

When you’re done exploring for the day, you’ll return to Rome and your accommodation.

Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

After savoring a delicious meal, step into the vibrant nightlife at Sant' Eustachio Caffè, where the evening is just getting started. In the same way, Yellowsquare Rome offers a unique charm perfect for experiencing the local bar scene in Rome. Caffè Portofino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

On day 11 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Naples. When you’re not sightseeing, take time to relax at your selected hotel in Naples, where you’ll be staying for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Spaccanapoli, a worthwhile street in the city. Then, head to Napoli Sotterranea Percorso Ufficiale and soak in the ambiance of this photogenic cave system.

There are many interesting places to see in Rome, and when you are ready for more, go to Cappella Sansevero. This is one of the city’s most locally renowned detailed spots of interest. After exploring the museum, visit the well-known Naples National Archaeological Museum. Not far away, you'll also find Piazza Del Plebiscito. This public square is an enchanting highlight in Rome.

At the end of the day, you will drive to Naples, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Naples's best restaurants.

Savor the flavors at L'Oca Nera Irish Pub, a top pick for dinner tonight. Alternatively, Mimì alla Ferrovia beckons with its unique menu offerings. Also, consider Spuzzulè Winebar. With its consistent customer satisfaction, it’s an excellent option for dining in Naples tonight.

Round off your dining experience by visiting Happening Cocktail Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Shanti Art Musik Bar, a bar catering to every mood and preference. Gran Caffè Gambrinus likewise offers a unique atmosphere, perfect for a memorable night out.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 12 of your road trip, you will have an entire day to explore Pompei. You’ll stay in Naples for 1 night and discover all the best things to see and do in the area.

Today’s agenda in Naples includes an archeological site, a castle, and a volcano. Archaeological Park Of Pompeii is must-visit archeological site and a great starting point for the day. Next, continue your journey to Basilica, an increasingly popular archeological site, located just a leisurely stroll away. Next, head to Castel Sant'elmo, a picture-perfect castle, also available for your discovery today.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Naples's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining at Antica Pizzeria Di Matteo, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Mercure Napoli Centro Angioino, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Lazzara Trattoria e Pizzeria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.

If you’re not ready to end the night just yet, Archivio Storico - Cocktail Bar & Wonderfood offers a perfect venue to relax and savor a drink. Similarly, Archeobar is well-suited for those looking to unwind in a social setting. Babette Pub is another excellent spot to enjoy a nightcap after a delightful meal.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Embark on another extraordinary experience on day 13 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Amalfi and Alberi. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Bring your curiosity for today’s adventure around Naples. Some of the village’s most loved attractions await! Amalfi Coast is the perfect place to start. This coast is one of the most impressive places to visit in Naples. Next, head to Saint Andrew's Fountain Amalfi, a beloved monument, known for its picture-perfect 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 Belvedere Sorrento. This romantic observation deck is a highly recommended experience. Visit these for an interesting touch to your journey.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a delicious dinner at Tijuana, an excellent option for tonight's dining. Looking for something different? Djària - American Bar offers a tantalizing alternative with its diverse menu. And don’t miss The Florence Irish Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Take some time to reflect on your day and savor another beautiful night in Italy.