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.

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.

Start by visiting Ponte Vecchio, a prime spot to begin your journey. This symbolic historical landmark is sure to impress. Next on your list is Uffizi Gallery, another must-visit landmark and astonishing art gallery renowned for its history-steeped 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 Della Signoria. This grand public square is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Basilica Of Santa Croce In Florence, a well-known church. Nearby, you'll also find Piazzale Michelangelo, ready to add charm to your journey.

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 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.

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.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s agenda in Florence includes a public square, a monument, and a historical landmark. Piazza Del Duomo, Pisa is must-visit public square and a great starting point for the day. Next, continue your journey to Leaning Tower Of Pisa, an iconic monument, located just a leisurely stroll away. Next, head to Piazza Dell'anfiteatro, an enchanting public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the curiosity-inducing Guinigi Tower. If you’re looking for more, Mura Di Lucca is also a locally appreciated attraction that is worthwhile a visit.

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.

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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

Get a good night's sleep and look forward to another great day on the road 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 vibrant destinations - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in San Gimignano. You will spend 1 night here for some well-deserved relaxation.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the popular Siena Cathedral, an enchanting church in Florence. Next, go to Piazza Del Campo.

After visiting Siena Cathedral and Piazza Del Campo, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Tower Of Mangia. This historic monument offers a unique experience. Parco Della Rocca is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Palazzo Comunale, Pinacoteca, Torre Grossa, one of the most awe-inspiring places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Piazza Del Duomo.

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.

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

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

Get ready for a day filled with fun adventures, photo-friendly spots, and history-rich sites in the charming village of San Gimignano. Your adventure starts at Chiesa Di Sant'agostino, an underrated local hot spot. Another notable attraction to explore is Etruscan Museum "mario Guarnacci". This up-and-coming museum is known for its photogenic appeal.

After soaking in the highlights of these sights, take some time to wander San Gimignano's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Porta A Selci. This culturally significant monument offers a fascinating experience that many visitors find memorable. Castello Di Tignano is also worth visiting.

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

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.

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

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

Greve in Chianti is brimming with adventures. Today’s wonderful stops include a castle and an archeological site. Begin your sightseeing adventure at the frequently visited Castello Di Brolio and allow yourself time to explore. Just a short distance away you'll find your next stop, Tumulo Di Montecalvario, an eye-catching archeological site that draws visitors from far and near.

Continue your journey to Rocca Di Castellina In Chianti, one of the hamlet’s most intriguing spots that you shouldn’t miss.

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

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

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

Today’s itinerary in Greve in Chianti covers several incredible sights, including a church, a public square, a castle, a monument and much more! Start your adventure at Basilica Of San Francesco D'assisi. This popular church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Piazza Del Comune, a must-see public square in the town.

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 Rocca Maggiore. This up-and-coming castle offers an enriching experience. For a change of pace, head to Perugia Cathedral, where you can take in instagrammable features. Conclude your self-guided sightseeing tour with a visit to Piazza Iv Novembre and The Fontana Maggiore. These sights offer a fulfilling end to a perfect day.

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.

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

Treat yourself to a delightful dinner at Ristorante Settimo Sigillo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Caffè Baglioni? It's another excellent option with a diverse menu. Consider reserving a table at Bar Pellas as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

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

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Perugia and Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Orvieto, which will be your home away from home for 1 night.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Perugia. Begin your sightseeing with Carducci Gardens. This underrated park is one of the top attractions in the city. Proceed to Well Of St. Patrick, another must-visit attraction.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Orvieto Cathedral. This notable church is a traveler-favorite. Not far away, you’ll find Orvieto Underground, another key site on your sightseeing itinerary. Pozzo Della Cava is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Rome and Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 2 nights.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Piazza Di Spagna. This globally renowned public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Vatican Museums, one of the city’s best highlights.

Next, check out Sistine Chapel, one of the most top-rated places to see in Orvieto. This chapel is a favorite among locals and travelers alike.

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 you explore more of Rome, 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.

Make sure to reserve a table at La Bottega Roma, 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 Pasta In Corso, 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 Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Celebrate another amazing day of your road trip adventure 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.

Monti is a fantastic place you can explore today in Rome. 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 Rome-way-of-life and visit all the nearby sights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Piazza Navona. This timeless public square provides an insightful glimpse into the city's identity. Next, discover Pantheon, a culturally significant monument, promising a delightful encounter.

Continue your sightseeing with a visit to Trevi Fountain, an iconic monument. When you’re done, don’t forget to make a stop at the world-famous Roman Forum. Round off your day at Colosseum, another gem in Rome with culturally significant features to discover.

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 Rome, 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.

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.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

Head back to your accommodation in Rome and get some rest in preparation for another magical day 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 vibrant destinations - Ottaviano and Naples. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Naples. You will spend 2 nights here for some well-deserved relaxation.

Today’s agenda in Rome includes a volcano, a castle, and a public square. Mount Vesuvius is must-visit volcano and a great starting point for the day. Next, continue your journey to Castel Sant'elmo, a popular castle, located just a leisurely stroll away. Next, head to Piazza Del Plebiscito, a respected public square, also available for your discovery today.

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.

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

Make sure to reserve a table at L'Oca Nera Irish Pub, an iconic dining spot in Naples. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Mimì alla Ferrovia, a popular restaurant in Naples. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Spuzzulè Winebar, a hidden gem nestled in Naples. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

On day 12 of your road trip in Italy, you’ll start and end your day in Naples, but spend the day exploring what’s beyond the city. Since you will return to Naples for 1 night more, there’s no need to rush. Experience Pompei and Naples to the fullest today with this curated day itinerary!

Bring your curiosity for today’s adventure around Naples. Some of the town’s most loved attractions await! Archaeological Park Of Pompeii is the perfect place to start. This archeological site is one of the most popular places to visit in Naples. Next, head to Basilica, a worthwhile archeological site, known for its instagrammable 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 Spaccanapoli. This standout street is a highly recommended experience. Nearby, you'll also find Napoli Sotterranea Percorso Ufficiale and Naples National Archaeological Museum. Visit these for an interesting touch to your journey.

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

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.

Treat yourself to a wonderful meal at Antica Pizzeria Di Matteo, a top-rated dining spot in Naples. If you're in the mood for something new, try Mercure Napoli Centro Angioino, another premier location with a delectable menu. You might also want to book a table at La Lazzara Trattoria e Pizzeria. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Naples.

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

As the sun sets on another day of adventure, rest up and recharge for the next leg 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 route brings fun adventures, scenic views, and picturesque spots. The first attraction of today is Amalfi Coast. Continue your discovery at Saint Andrew's Fountain Amalfi, a historic monument with stories to tell.

As you stroll around Naples, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Belvedere Sorrento. This increasingly popular observation deck offers a romantic encounter with Naples. 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.

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.

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

Don’t miss out on dining at Tijuana, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Djària - American Bar, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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