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

Day 2 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Oltrarno is a fantastic place you can explore today in Florence. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Florence-way-of-life and visit all the nearby sights.

Experience Ponte Vecchio, a globally renowned historical landmark in the city. Then, head to Uffizi Gallery and soak in the ambiance of this history-steeped 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 famous romantic spots of interest. After exploring the public square, visit the locally renowned Basilica Of Santa Croce In Florence. Not far away, you'll also find Piazzale Michelangelo. This observation deck is an enchanting highlight in Florence.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

On day 3 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary.

Continue your road trip and head to your next destination, Pisa. This car ride takes around 1 hour 16 min.

For a more meaningful self-guided tour of the city's best attractions, visit Piazza Del Duomo, Pisa, an iconic public square that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Leaning Tower Of Pisa and admire its historic features.

Fasten your seatbelt and make your way to your next stop — Lucca, home to many well-known sights in the region. Keep in mind that your travel time from Pisa to Lucca may take around 32 min without traffic disruptions. Upon arrival in Lucca, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Piazza Dell'anfiteatro. Spend some time admiring the romantic features of the public square before you continue to your next stop. Then, head to Guinigi Tower. This beloved monument is a traveler-favorite in the city.

If you're keen to see more, continue to Mura Di Lucca. Feed your curiosity by learning something new about the historical landmark.

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

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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

Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Siena and San Gimignano. At the end of the day, you will retreat to the hotel of your choice in San Gimignano, where will spend 1 night.

Fasten your seatbelt and make your way to your next stop — Siena, home to many well-known sights in the region. Keep in mind that your travel time from Florence to Siena may take around 1 hour 12 min without traffic disruptions. Upon arrival in Siena, we highly recommend checking out some of the top attractions.

Spend your afternoon discovering Siena Cathedral, a locally renowned church known for its visually striking features. Next, continue your sightseeing at Piazza Del Campo, an extraordinary public square.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Tower Of Mangia and uncover the details of this UNESCO world heritage-listed monument.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of San Gimignano. This drive usually takes around 47 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Parco Della Rocca, an increasingly popular park that everyone visiting San Gimignano should see. Next, head to Palazzo Comunale, Pinacoteca, Torre Grossa. This culturally significant museum is one of the most increasingly popular attractions in the region.

If you're keen to see more, don’t miss out on Piazza Del Duomo, a symbolic public square popular among locals as well as travelers.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine.

Relax and look forward to more memorable moments to come!

On day 5 of your road trip in Italy, your travel plans include 3 stops at the most scenic, wondrous, and interesting places in the region. San Gimignano, Volterra, and Tignano are on today's agenda. In the evening, you’ll end up in Greve in Chianti, where you will stay for 2 nights.

Chiesa Di Sant'agostino brings San Gimignano's character to life. This culturally significant church is a highlight of any visit in the village.

Set your GPS to Volterra and hit the road. Expect a journey of approximately 40 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Volterra beckons with new experiences!

Spend your afternoon discovering Etruscan Museum "mario Guarnacci", a frequently visited museum known for its heritage-rich features. Next, continue your sightseeing at Porta A Selci, a beloved monument.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Tignano. This drive usually takes around 1 hour 12 min, without any stops or traffic disruptions.

Savor the day by heading to Castello Di Tignano, a beloved castle that draws visitors from near and far.

When you’re done exploring for the day, you’ll drive to your hotel in Greve in Chianti. Check in and relax before you head out to tour the town.

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

As the sun sets, rest up and recharge for the next leg 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 have 1 night to stay in Greve in Chianti, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in San Regolo and Castellina in Chianti.

After soaking in Greve in Chianti’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: San Regolo. Expect your car journey to take a minimum of 48 min. When you arrive in San Regolo, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Castello Di Brolio. Spend some time admiring the visually striking features of the castle before you continue to your next stop.

After soaking in San Regolo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Castellina in Chianti. Expect your car journey to take a minimum of 40 min. When you arrive in Castellina in Chianti, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Tumulo Di Montecalvario and explore the symbolic features. Next, make your way to Rocca Di Castellina In Chianti, another highlight in Castellina in Chianti.

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

Indulge in a memorable dining experience at one of Greve in Chianti's most popular restaurants, and connect with friendly locals for a true cultural experience.

Relax and recharge in preparation for another adventurous day in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your chosen hotel in Perugia, where you’ll be staying for 1 night.

Set your GPS to Santa Maria degli Angeli and hit the road. Expect a journey of approximately 2 hours 10 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Santa Maria degli Angeli beckons with new experiences!

Basilica Of San Francesco D'assisi is a popular church we recommend visiting today. Discover its picture-perfect features before continuing your self-guided tour to Piazza Del Comune, an enchanting public square that’s well-regarded in the area.

Next, stop by Rocca Maggiore, a history-steeped castle.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Perugia. This drive usually takes around 34 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the town's best attractions, visit Perugia Cathedral, a beloved church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Piazza Iv Novembre and admire its romantic features.

When you’re ready, continue to The Fontana Maggiore, an up-and-coming monument beloved by locals and tourists alike.

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

Enjoy a delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

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

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Your itinerary for day 8 of your road trip in Italy includes 2 stops and features some of the highlights of Perugia and Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 1 night.

To truly experience Perugia, make sure to drop by Carducci Gardens. This frequently visited park is a must-visit for anyone seeking a unique vacation experience.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Perugia behind. This drive usually takes around 1 hour 12 min. Orvieto welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Well Of St. Patrick, an interesting monument in Orvieto. Explore its awe-inspiring features at your own pace before you continue your journey.

After soaking in Perugia’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 12 min. When you arrive in Orvieto, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Orvieto Cathedral, a popular church that everyone visiting Orvieto should see. Next, head to Orvieto Underground. This photogenic cave system is one of the most locally appreciated attractions in the region.

If you're keen to see more, don’t miss out on Pozzo Della Cava, an eye-catching cave popular among locals as well as travelers.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Duomo, a well-loved spot among locals and tourists.

Savor another day of unforgettable experiences in Italy!

Dive into day 9 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Rome and Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 2 nights.

When you’re ready to jump back into the car and say goodbye to Orvieto, you’ll hit the road in the direction of Rome. This drive usually takes around 1 hour 33 min.

Set out on a self-guided sightseeing tour at Piazza Di Spagna and explore the romantic features.

When you arrive in Vatican City, it's time to take a break from the road.

Next, make your way to Sistine Chapel, another highlight in Vatican City.

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

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

Treat yourself to a wonderful meal at La Bottega Roma, a top-rated dining spot in Rome. If you're in the mood for something new, try Pasta In Corso, another premier location with a delectable menu. You might also want to book a table at Trattoria Vecchia Roma. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

On day 10 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 1 night.

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

Make a stop at Piazza Navona. This world-famous public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Pantheon located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Trevi Fountain. Its romantic features will captivate you. After the monument, continue your tour of the city with a visit to Roman Forum. Visitors usually appreciate the picture-perfect features of this archeological site. Next up is Colosseum, a highly recommended archeological site.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Ottaviano and Naples. At the end of the day, you will retreat to the hotel of your choice in Naples, where will spend 2 nights.

Continue your road trip and head to your next destination, Ottaviano. This car ride takes around 2 hours 44 min.

Savor the day by heading to Mount Vesuvius, an underrated volcano that draws visitors from near and far.

When you’ve had your share of Ottaviano, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Naples. Your travel time is around 56 min.

Our first attraction recommendation in Naples is Castel Sant'elmo, a locally renowned castle that draws attention for its historic features. Spend some time soaking in the atmosphere before continuing to Piazza Del Plebiscito, a visually striking public square that stands out in the city.

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.

Naples is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Naples.

Treat yourself to a delightful dinner at L'Oca Nera Irish Pub, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mimì alla Ferrovia? It's another excellent option with a diverse menu. Consider reserving a table at Spuzzulè Winebar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Naples.

Continue your evening by exploring the vibrant nightlife scene at Happening Cocktail Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Shanti Art Musik Bar, a bar that offers unique local touches. Likewise, Gran Caffè Gambrinus provides an excellent alternative for a fun evening.

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

On day 12 of your road trip, you'll get the chance to experience Pompei and Naples. At the end of the day, you'll drive back to Naples, where you still have 1 night left to stay.

Check out the curiosity-inducing street, Spaccanapoli. Afterward, continue to Napoli Sotterranea Percorso Ufficiale, a cave system every traveler should visit. As you explore Naples’s charming streets, take in the lively atmosphere and get to know the character of the town.

Next, make your way to Naples National Archaeological Museum. This locally renowned museum is an essential stop.

Fasten your seatbelt and make your way to your next stop — Pompei, home to many well-known sights in the region. Keep in mind that your travel time from Naples to Pompei may take around 27 min without traffic disruptions. Upon arrival in Pompei, we highly recommend checking out some of the top attractions.

Archaeological Park Of Pompeii is a popular archeological site we recommend visiting today. Discover its picture-perfect features before continuing your self-guided tour to Basilica, an UNESCO world heritage-designated archeological site that’s well-regarded in the area.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Naples. Enjoy a relaxing evening as you savor delicious local cuisine.

Enjoy a delicious meal at Antica Pizzeria Di Matteo, a highly-rated dining destination in Naples. If you're eager to try something different, consider Mercure Napoli Centro Angioino, another top spot with a tantalizing menu. You might also want to secure a reservation at La Lazzara Trattoria e Pizzeria. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Naples this evening.

After enjoying a fulfilling meal, continue your evening at Archivio Storico - Cocktail Bar & Wonderfood, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Archeobar offers a welcoming atmosphere for easing into the nightlife. Similarly, Babette Pub provides an excellent environment for a relaxed and enjoyable evening.

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

On day 13 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Amalfi and Alberi are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Amalfi’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Naples behind. This drive usually takes around 1 hour 26 min. Amalfi welcomes you with a multitude of unique vacation experiences.

Spend some time soaking in the atmosphere before continuing to Saint Andrew's Fountain Amalfi, a picture-perfect monument that stands out in the village.

Fasten your seatbelt and make your way to your next stop — Alberi, home to many well-known sights in the region. Keep in mind that your travel time from Amalfi to Alberi may take around 1 hour 4 min without traffic disruptions. Upon arrival in Alberi, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Belvedere Sorrento. Spend some time admiring the visually striking features of the observation deck before you continue to your next stop.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Make sure to reserve a table at Tijuana, 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 Djària - American Bar, 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 The Florence Irish Pub, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Raise your glass to another unforgettable day in Italy!