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

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

Oltrarno is a neighborhood that stands out as one of the must-see places in Florence. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Ponte Vecchio. This visually striking historical landmark is a highlight of any visit in the city. Then, enjoy Uffizi Gallery, another romantic attraction that never fails to captivate visitors. Next, head over to Piazza Della Signoria, one of the city’s most famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Of Santa Croce In Florence. This heritage-rich church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazzale Michelangelo, a widely recognized observation deck, and take a stroll around the area.

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 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.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

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.

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.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo, Pisa. This world-famous public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Leaning Tower Of Pisa, one of the city’s best highlights.

Next, check out Piazza Dell'anfiteatro, one of the most locally renowned places to see in Florence. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Guinigi Tower. Wander around and soak in the symbolic atmosphere this monument offers. Then, head to Mura Di Lucca, a top-rated historical landmark that adds another dimension to your day.

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

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.

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

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.

Savor another day of unforgettable experiences in Italy!

On day 4 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 Siena and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Florence on today’s itinerary. First up is the locally renowned church, Siena Cathedral. Afterward, continue to Piazza Del Campo, a public square every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Tower Of Mangia. This up-and-coming monument is an essential stop. Following that, head to Parco Della Rocca, another must-visit site that will enhance your experience. Don’t forget to stop by Palazzo Comunale, Pinacoteca, Torre Grossa, a beloved museum in the city. Finally, end your day with a visit to Piazza Del Duomo, an UNESCO world heritage-listed public square that offers the perfect conclusion to your sightseeing of the day.

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.

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

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

San Gimignano is brimming with adventures. Today’s wonderful stops include a church, a museum, a monument, a castle and much more! Begin your sightseeing adventure at the beloved Chiesa Di Sant'agostino and allow yourself time to explore. Just a short distance away you'll find your next stop, Etruscan Museum "mario Guarnacci", an instagrammable museum that draws visitors from far and near.

Continue your journey to Porta A Selci, one of the village’s most intriguing spots that you shouldn’t miss. Another great site to visit is the up-and-coming Castello Di Tignano.

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.

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.

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

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

Enjoy the perfect balance of relaxation and exploration in Greve in Chianti today. One of the most worthwhile attractions included on the itinerary is Castello Di Brolio. This romantic castle will help you start your sightseeing on top. Then, take a leisurely stroll to Tumulo Di Montecalvario and learn what makes this symbolic archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the intriguing Rocca Di Castellina In Chianti.

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

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

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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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 Perugia. You’ll stay here for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, breathtaking views, and photo-friendly spots. Whether you decide to explore Greve in Chianti on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Basilica Of San Francesco D'assisi is the first of them. Spend some time admiring this picture-perfect church before continuing your journey. Piazza Del Comune is your next stop. This frequently visited public square is one of the best-rated sights in Greve in Chianti.

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 Rocca Maggiore. This visually striking castle is a sight to behold. To round off your sightseeing experience, visit Perugia Cathedral and Piazza Iv Novembre. If time allows, end your day with The Fontana Maggiore, a noteworthy monument that offers a memorable conclusion to your exploration.

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

As you explore more of Perugia, 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 Ristorante Settimo Sigillo, a top-rated dining spot in Perugia. If you're in the mood for something new, try Caffè Baglioni, another premier location with a delectable menu. You might also want to book a table at Bar Pellas. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Perugia.

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.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Perugia and Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Orvieto. You will spend 1 night here for some well-deserved relaxation.

Today’s agenda in Perugia includes a park, a monument, a church, a cave system, a cave and much more! Carducci Gardens is must-visit park and a great starting point for the day. Next, continue your journey to Well Of St. Patrick, a captivating monument, located just a leisurely stroll away. Next, head to Orvieto Cathedral, a history-steeped church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Perugia. When you're ready, let your sightseeing route take you to the frequently visited Orvieto Underground. If you’re looking for more, Pozzo Della Cava is also a frequently visited attraction that is worthwhile a visit.

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.

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

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

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

On day 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.

Start your day with a visit to Piazza Di Spagna. This iconic public square is a must-visit in the city.

One of the best things about exploring Orvieto on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Sistine Chapel, a widely recognized chapel in the city. If you’re up for more discoveries, don’t forget to reserve some time for St. Peter's Basilica.

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

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

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.

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

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do 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.

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Rome. Your adventure starts at Piazza Navona, an iconic local hot spot. Another notable attraction to explore is Pantheon. This wondrous monument is known for its majestic appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Trevi Fountain. This visually striking monument offers a fascinating experience that many visitors find memorable. Roman Forum is also worth visiting, along with Colosseum. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 11 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 Ottaviano and Naples. In the evening, you’ll end up in Naples, where you will stay for 2 nights.

Today’s route brings fun adventures, natural wonders, and breathtaking views. The first attraction of today is Mount Vesuvius. This worthwhile volcano is a stunning place to see in Rome. Continue your discovery at Castel Sant'elmo, a historic castle with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Plebiscito. This top-rated public square offers a romantic encounter with Rome. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Naples. Naples 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 Naples's best restaurants.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Happening Cocktail Bar, known for its inviting atmosphere. Shanti Art Musik Bar is another great option if you’re looking for a place to get the night started. Similarly, Gran Caffè Gambrinus provides a great setting to enjoy the night away.

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

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!

Set out on a day brimming with fun adventures, scenic views, and picturesque spots. Start at the well-known Archaeological Park Of Pompeii, a breathtaking archeological site in Naples. Next, go to Basilica.

After visiting Archaeological Park Of Pompeii and Basilica, have a stroll along Naples's streets and take in the local charm. Continue your sightseeing by heading to Spaccanapoli. This visually striking street offers a unique experience. Napoli Sotterranea Percorso Ufficiale is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Naples National Archaeological Museum, one of the most instagrammable places to visit in Naples.

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

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.

Make sure to reserve a table at Antica Pizzeria Di Matteo, 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 Mercure Napoli Centro Angioino, 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 La Lazzara Trattoria e Pizzeria, a hidden gem nestled in Naples. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

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

Set out on a day brimming with fun adventures, scenic views, and picturesque spots. Next, go to Saint Andrew's Fountain Amalfi.

After visiting Amalfi Coast and Saint Andrew's Fountain Amalfi, have a stroll along Naples's streets and take in the local charm. Continue your sightseeing by heading to Belvedere Sorrento. This romantic observation deck offers a unique experience.

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.

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