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

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

A visit to Oltrarno in Florence 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.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, a public square, an art gallery, a historical landmark, a botanical garden and much more! Begin your adventure at Basilica Of Santa Croce In Florence. This is a well-known church you should not miss. Another must-see is Piazza Della Signoria, a top-rated public square in Florence.

When you’re ready for the next sight, head to Uffizi Gallery. From there, take a leisurely stroll to Ponte Vecchio, another of the city’s timeless attractions. We recommend continuing your self-guided tour at The Boboli Gardens, a masterful 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 Florence's best restaurants.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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

On day 3 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pisa and Lucca. You still have 1 night left in Florence.

Florence is brimming with adventures. Today’s wonderful stops include a public square, a monument, and a historical landmark. Begin your sightseeing adventure at the iconic Piazza Del Duomo, Pisa and allow yourself time to explore. Just a short distance away you'll find your next stop, Leaning Tower Of Pisa, a historic monument that draws visitors from far and near.

Continue your journey to Piazza Dell'anfiteatro, one of the city’s most well-known spots that you shouldn’t miss. Another great site to visit is the frequently visited Guinigi Tower. When you're finished at the monument, Mura Di Lucca awaits your visit. This historical landmark is a history-steeped highlight on today's itinerary.

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

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Continue your lively evening at Gosh*, a perfect place for winding down or revving up the night, depending on which mood you’re in. Antico Caffè Del Moro - Art Bar Firenze is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Quelo Bar ensures a night out tailored to your taste.

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.

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 breathtaking views. Start at the popular Siena Cathedral, an enchanting church in Florence. Next, go to Facciatone.

After visiting Siena Cathedral and Facciatone, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Campo. This visually striking public square offers a unique experience. Tower Of Mangia is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Porta San Giovanni, one of the most picture-perfect places to visit in Florence.

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

With its reputation for pleasing customers, it’s a fantastic choice for tonight in San Gimignano.

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

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

Immerse yourself in San Gimignano’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Del Duomo. This enchanting public square is sure to ignite your curiosity. Next, dive into the visually striking features of Parco Della Rocca, a must-visit park in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Etruscan Museum "mario Guarnacci", a worthwhile museum. For a change of scene, check out Porta A Selci, known for its historic features. We also recommend visiting Poggio Amorelli. This winery is a must for anyone looking to experience the village to the fullest.

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

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

Wake up to day 6 of your extraordinary road trip in Italy. With 1 night left in Panzano in Chianti, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Castello Di Brolio. This locally appreciated castle is a romantic place to see in Panzano in Chianti. Continue your discovery at Tumulo Di Montecalvario, a symbolic archeological site with stories to tell.

As you stroll around Panzano in Chianti, take in the distinct atmosphere and learn what makes this hamlet so unique. Maximize your sightseeing with a visit to Rocca Di Castellina In Chianti. This up-and-coming castle offers a grand encounter with Panzano in Chianti. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Panzano in Chianti.

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.

Relax and recharge in preparation for another adventurous day 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 itinerary in Panzano in Chianti covers several incredible sights, 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 place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Rocca Maggiore, a must-see castle 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 Perugia Sotterranea Accesso. This underrated cave system offers an enriching experience. For a change of pace, head to Perugia Cathedral, where you can take in culturally significant 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.

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 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.

Make sure to reserve a table at Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. 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 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.

Savor another day of unforgettable experiences in Italy!

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Perugia and Orvieto. When you’re not sightseeing, take time to relax at your selected hotel in Orvieto, where you’ll be staying for 1 night.

Enjoy the perfect balance of relaxation and exploration in Perugia today. One of the most underrated attractions included on the itinerary is Carducci Gardens. This visually striking park will help you start your sightseeing on top. Then, take a leisurely stroll to Orvieto Cathedral and learn what makes this inviting church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Orvieto Underground. After exploring the cave system, head to Pozzo Della Cava. This locally appreciated cave is a highlight in Perugia.

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.

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.

Following your dinner, dive into the local bar culture at Bar Duomo. Enjoy this evening's relaxed ambiance with delightful drinks.

Raise your glass to another unforgettable day in Italy!

On day 9 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 Rome. In the evening, you’ll end up in Rome, where you will stay for 2 nights.

Prepare for a day full of family-friendly attractions, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Colosseum. This wondrous archeological site is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Roman Forum, one of the city’s best highlights.

Next, check out Trevi Fountain, one of the most timeless places to see in Orvieto. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pantheon. Wander around and soak in the culturally significant atmosphere this monument offers. Then, head to Piazza Navona, a top-rated public square that adds another dimension to your day.

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.

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

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.

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

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

A top thing to do today is to explore Trastevere, a must-see neighborhood in Vatican City. It's the perfect starting point for touring the top attractions in the area. You can also visit Via del Corso, an ideal street for continued sightseeing.

Start your day at Vatican Museums. Then, wander over to Sistine Chapel. Nearby, you’ll also find St. Peter's Basilica.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Di Spagna is a globally renowned spot in the city that will captivate you with its unique charm.

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

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

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Sant' Eustachio Caffè, known for its inviting atmosphere. Yellowsquare Rome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

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 1 vibrant destinations - 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.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a street, a cave system, a museum, a public square and much more! Begin your adventure at Spaccanapoli. This is an up-and-coming street you should not miss. Another must-see is Napoli Sotterranea Percorso Ufficiale, an interesting cave system in Rome.

When you’re ready for the next sight, head to Cappella Sansevero. From there, take a leisurely stroll to Naples National Archaeological Museum, another of the city’s captivating attractions. We recommend continuing your self-guided tour at Piazza Del Plebiscito, a majestic place of interest in the city.

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.

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

Enjoy a delicious meal at L'Oca Nera Irish Pub, a highly-rated dining destination in Naples. If you're eager to try something different, consider Mimì alla Ferrovia, another top spot with a tantalizing menu. You might also want to secure a reservation at Spuzzulè Winebar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Naples this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Happening Cocktail Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Shanti Art Musik Bar offers an ideal atmosphere to enjoy the pleasures of the night. Gran Caffè Gambrinus is also a great option that provides a perfect setting for a relaxing evening.

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

Day 12 offers a multitude of experiences. You will stay in Naples for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s route brings fun adventures, scenic views, and photo-friendly spots. The first attraction of today is Archaeological Park Of Pompeii. This notable archeological site is an UNESCO world heritage-listed 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 Castel Sant'elmo. This notable castle offers a culturally significant encounter with Naples. Next, make your way to Mount Vesuvius to add another highlight to your day. 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.

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 dinnertime approaches, it's time to head out for a bite to eat in Naples. 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 lovely meal at Antica Pizzeria Di Matteo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Mercure Napoli Centro Angioino is another top choice with a popular menu. You could also check for a table at La Lazzara Trattoria e Pizzeria. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Naples tonight.

Following your dinner, dive into the local bar culture at Archivio Storico - Cocktail Bar & Wonderfood. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Archeobar, the perfect place for those looking to experience the best of the nightlife. Similarly, Babette Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 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.

Start your day at Amalfi Coast. Then, wander over to Saint Andrew's Fountain Amalfi. If picture-perfect sites excite you, this monument will be right up your alley. Nearby, you’ll also find Belvedere Sorrento. This romantic observation deck is a favorite among visitors.

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 dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

Treat yourself to a delightful dinner at Tijuana, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Djària - American Bar? It's another excellent option with a diverse menu. Consider reserving a table at The Florence Irish Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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