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 a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Savor the day by visiting some of the best places to see in Florence, including a historical landmark, an art gallery, a public square, a church, an observation deck and much more! Start your adventure at Ponte Vecchio. This wondrous historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Uffizi Gallery located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Della Signoria. Its enchanting features will captivate you. After the public square, continue your tour of the city with a visit to Basilica Of Santa Croce In Florence. Visitors usually appreciate the heritage-rich features of this church. Next up is Piazzale Michelangelo, a highly recommended observation deck.

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

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city 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 Pisa and Lucca.

Start by visiting Piazza Del Duomo, Pisa, a prime spot to begin your journey. This stunning public square is sure to impress. Next on your list is Leaning Tower Of Pisa, another must-visit landmark and world-famous monument renowned for its UNESCO world heritage-listed features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Dell'anfiteatro. This romantic public square is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Guinigi Tower, an up-and-coming monument. Nearby, you'll also find Mura Di Lucca, ready to add charm to your journey.

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

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

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.

Unwind after your meal by stepping into Gosh*. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Quelo Bar, another top-rated bar in the area.

Celebrate another amazing day of your road trip adventure 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 family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Florence. Your adventure starts at Siena Cathedral, a captivating local hot spot. Another notable attraction to explore is Piazza Del Campo. This spectacular public square is known for its inviting 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 Tower Of Mangia. This historic monument offers a fascinating experience that many visitors find memorable. Parco Della Rocca is also worth visiting, along with Palazzo Comunale, Pinacoteca, Torre Grossa. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Del Duomo. This curiosity-inducing public square provides a fitting finale to your sightseeing.

At the end of the day, you will drive to San Gimignano, 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 San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Raise your glass to another unforgettable day in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you will explore San Gimignano, Volterra, and Tignano, 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 Greve in Chianti. You’ll stay here for 2 nights.

A blend of family-friendly attractions, picturesque spots, and historic treasures await you in San Gimignano on today’s itinerary. First up is the worthwhile church, Chiesa Di Sant'agostino. Afterward, continue to Etruscan Museum "mario Guarnacci", a museum every traveler should visit.

As you explore San Gimignano’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Porta A Selci. This locally appreciated monument is an essential stop. Following that, head to Castello Di Tignano, another must-visit site that will enhance your experience.

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

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

Savor another day of unforgettable experiences in Italy!

On day 6 of your road trip in Italy, you’ll start and end your day in Greve in Chianti, but spend the day exploring what’s beyond the town. Since you will return to Greve in Chianti for 1 night more, there’s no need to rush. Experience San Regolo and Castellina in Chianti to the fullest today with this curated day itinerary!

Get ready to discover some of the most iconic wonders in Greve in Chianti, including a castle and an archeological site. Start your day at Castello Di Brolio. This visually striking castle is an intriguing place to see in Greve in Chianti. Then, wander over to Tumulo Di Montecalvario. If symbolic sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Rocca Di Castellina In Chianti. This visually striking castle is a favorite among visitors.

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 an authentic adventure.

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 1 night.

Today’s route brings family-friendly attractions, breathtaking views, and photo-friendly spots. The first attraction of today is Basilica Of San Francesco D'assisi. This popular church is a picture-perfect place to see in Greve in Chianti. Continue your discovery at Piazza Del Comune, a symbolic public square with stories to tell.

As you stroll around Greve in Chianti, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Rocca Maggiore. This underrated castle offers a visually striking encounter with Greve in Chianti. Next, make your way to Perugia Cathedral to add another highlight to your day. After that, visit Piazza Iv Novembre, a beloved public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at The Fontana Maggiore, an intriguing monument in the town. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Greve in Chianti.

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

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

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

Continue your lively evening at Tommi Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Valentina is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffe Dal Perugino ensures a night out tailored to your taste.

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

On day 8 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 Perugia and Orvieto. In the evening, you’ll end up in Orvieto, where you will stay for 1 night.

Get ready for an exciting day in Perugia. Today’s sightseeing agenda includes a park, a monument, a church, a cave system, a cave and much more! Begin your adventure at Carducci Gardens. This is an intriguing park you should not miss. Another must-see is Well Of St. Patrick, a captivating monument in Perugia.

When you’re ready for the next sight, head to Orvieto Cathedral. From there, take a leisurely stroll to Orvieto Underground, another of the city’s locally appreciated attractions. We recommend continuing your self-guided tour at Pozzo Della Cava, a photogenic place of interest in the city.

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

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

Extend your evening after a delightful meal by visiting Bar Duomo, which offers the perfect atmosphere for a night out.

Get a good night's sleep and look forward to another great day on the road 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 2 vibrant destinations - Rome and Vatican City. 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.

Start your adventure at Piazza Di Spagna. This iconic public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Vatican Museums located in Orvieto for another exciting encounter.

Next, immerse yourself in the setting of Sistine Chapel. After the chapel, continue your tour of the city with a visit to St. Peter's Basilica.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome 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 Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

Day 10 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

A top thing to do today is to explore Monti, a must-see neighborhood in Rome. It's the perfect starting point for touring the top attractions in the area.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a public square, a monument, and an archeological site. Begin your adventure at Piazza Navona. This is a timeless public square you should not miss. Another must-see is Pantheon, a wondrous monument in Rome.

When you’re ready for the next sight, head to Trevi Fountain. From there, take a leisurely stroll to Roman Forum, another of the city’s world-famous attractions. We recommend continuing your self-guided tour at Colosseum, an awe-inspiring place of interest in the city.

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.

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

Make sure to reserve a table at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Mount Vesuvius. This instagrammable volcano is a highlight of any visit in the city. Then, enjoy Castel Sant'elmo, another historic attraction that never fails to captivate visitors. Next, head over to Piazza Del Plebiscito, one of the city’s most widely recognized attractions, known for its enchanting features.

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

As you explore more of Naples, 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 L'Oca Nera Irish Pub, a popular restaurant in Naples. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Naples at Mimì alla Ferrovia, 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 Spuzzulè Winebar. It’s yet another ideal choice to enhance your time in Naples tonight.

Unwind after your meal by stepping into Happening Cocktail Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Shanti Art Musik Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Gran Caffè Gambrinus, another top-rated bar in the area.

Celebrate another amazing day of your road trip adventure in Italy!

On day 12 of your road trip, you’ll start and end your day in Naples, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pompei and Naples. You still have 1 night left in Naples.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Archaeological Park Of Pompeii. This well-known archeological site is a breathtaking place to see in Naples. Continue your discovery at Basilica, an UNESCO world heritage-listed archeological site with stories to tell.

As you stroll around Naples, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Spaccanapoli. This beloved street offers a visually striking encounter with Naples. Next, make your way to Napoli Sotterranea Percorso Ufficiale to add another highlight to your day. After that, visit Naples National Archaeological Museum, a captivating museum 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 Naples.

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 and reflect on the day's adventures.

Dine in style at Antica Pizzeria Di Matteo, a top recommendation for dinner tonight. Or, for a change of pace, Mercure Napoli Centro Angioino boasts a menu that's sure to impress. Also, be sure to check out La Lazzara Trattoria e Pizzeria. Known as a local hotspot, it’s a great choice for tonight in Naples.

Continue your lively evening at Archivio Storico - Cocktail Bar & Wonderfood, a perfect place for winding down or revving up the night, depending on which mood you’re in. Archeobar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Babette Pub ensures a night out tailored to your taste.

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

Dive into day 13 of your remarkable road trip in Italy. Today you will explore Amalfi and Alberi, 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 Florence. You’ll stay here for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly spots. Whether you decide to explore Naples on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Amalfi Coast is the first of them. Saint Andrew's Fountain Amalfi is your next stop. This beloved monument is one of the best-rated sights in Naples.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Belvedere Sorrento. This romantic observation deck is a sight to behold.

At the end of the day, you will drive to Florence, 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at Tijuana, a top recommendation for dinner tonight. Or, for a change of pace, Djària - American Bar boasts a menu that's sure to impress. Also, be sure to check out The Florence Irish Pub. Known as a local hotspot, it’s a great choice for tonight in Florence.

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