14-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Perugia, Rome, and Naples

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Pisa. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 5 nights here for some well-deserved relaxation.

Continue your journey to Pisa Cathedral, one of the city’s most frequently visited spots that you shouldn’t miss. Another great site to visit is the timeless Piazza Del Duomo, Pisa. Last up on today’s itinerary is a cemetery. Make your way to Campo Santo for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Pisa.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence's best restaurants.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

On day 3 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 4 nights and discover all the best things to see and do in the area.

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a historical landmark, an art gallery, an observation deck and much more! Start your adventure at Cathedral Of Santa Maria Del Fiore. This top-rated church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Piazza Della Signoria, a must-see public square in the city.

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 Ponte Vecchio. This timeless historical landmark offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo and Piazzale Michelangelo. These sights offer a fulfilling end to a perfect day.

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.

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

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. 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 Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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

On day 4 of your road trip, you’ll start and end your day in Florence, where you'll stay for 3 nights more.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea (siena). This increasingly popular monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Palazzo Salimbeni, one of the city’s best highlights.

Next, check out Piazza Del Campo, one of the most top-rated 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, Pubblico Palace. Wander around and soak in the respected atmosphere this palace offers. Then, head to Siena Cathedral, a top-rated church that adds another dimension to your day.

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

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

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

Following your dinner, dive into the local bar culture at Gosh*. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Antico Caffè Del Moro - Art Bar Firenze, the perfect place for those looking to experience the best of the nightlife. Similarly, Quelo Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Greet day 5 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 2 nights 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 San Gimignano.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Parco Della Rocca, an underrated park in the village. Then, head to Rocca Di Montestaffoli and soak in the ambiance of this history-steeped castle.

There are many interesting places to see in Florence and when you are ready for more, go to Piazza Del Duomo. This is one of the village’s most up-and-coming spots. After exploring the public square, visit the underrated Sangimignano1300. Before wrapping up your self-guided sightseeing tour, head to the increasingly popular Porta San Giovanni, an increasingly popular monument in the village.

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.

Enjoy a delicious meal 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.

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

On day 6 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 Greve in Chianti, Greti, and Montefioralle. You still have 1 night left in Florence.

Today’s itinerary in Florence covers several incredible sights, including a castle and a winery. Start your adventure at Castle Of Verrazzano. This locally appreciated castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Villa Calcinaia - Conti Capponi, a must-see winery 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 Fattoria Viticcio. This locally appreciated winery offers an enriching experience.

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

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.

Enjoy a delicious meal at Ristorante Buca Niccolini, a highly-rated dining destination in Florence. If you're eager to try something different, consider Essenziale, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante La Grotta Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Raise your glass to another unforgettable day 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. In the evening, you’ll end up in Perugia, where you will stay for 2 nights.

Set out on a day brimming with fun adventures, scenic views, and picturesque spots. Start at the increasingly popular San Damiano, a stunning church in Florence. Next, go to Basilica Di Santa Chiara.

After visiting San Damiano and Basilica Di Santa Chiara, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Piazza Del Comune. This romantic public square offers a unique experience. Basilica Of San Francesco D'assisi is another noteworthy stop.

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

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

Following your dinner, dive into the local bar culture at Tommi Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Valentina, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffe Dal Perugino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 8 of your road trip across Italy promises a magnificent time exploring Perugia. You have 1 night left in Perugia. Take the opportunity to experience more of the best attractions and activities in the city.

Set out on a day brimming with fun adventures, picturesque spots, and history-rich sites. Start at the locally appreciated Chiesa Di San Michele Arcangelo, a photogenic church in Perugia. Next, go to Perugia Sotterranea Accesso.

After visiting Chiesa Di San Michele Arcangelo and Perugia Sotterranea Accesso, take time to explore Perugia's streets and absorb its charm. Continue your sightseeing by heading to Perugia Cathedral. This culturally significant church offers a unique experience. Piazza Iv Novembre is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Rocca Paolina, one of the most heritage-rich places to visit in Perugia.

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 Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Don’t miss out on dining at La Taverna, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Ristorante del Sole, another top spot with a mouthwatering menu. You might also want to secure a reservation at Al Mangiar Bene. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

Round off your dining experience by visiting Caffè Fortebraccio, a prime location for a drink. Alternatively, explore the distinctive characteristics of Caffe Del Banco, a bar catering to every mood and preference. Dempsey's Perugia likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Rome, 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 Rome. You’ll stay here for 2 nights.

Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming city of Perugia. Your adventure starts at Colosseum, an iconic local hot spot. Another notable attraction to explore is Roman Forum. This iconic archeological site is known for its UNESCO world heritage-designated appeal.

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

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 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.

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

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.

Wake up to day 10 of your extraordinary road trip in Italy. With 1 night left in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Trastevere is a fantastic place you can explore today in Vatican City. 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 Vatican City-way-of-life and visit all the nearby sights. You should also check out Monti, a neighborhood offering more opportunities to enjoy the city’s vibrant atmosphere and landmarks.

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

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.

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

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino 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.

On day 11 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Naples. When you’re not sightseeing, take time to relax at your selected hotel in Naples, where you’ll be staying for 2 nights.

A blend of family-friendly attractions, photo-friendly spots, and history-rich sites await you in Rome on today’s itinerary. First up is the locally renowned museum, Naples National Archaeological Museum. Afterward, continue to Ovo Castle, a castle every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Castel Nuovo. This popular castle is an essential stop. Following that, head to Piazza Del Plebiscito, another must-visit site that will enhance your experience.

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.

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

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

Keep the evening going at Happening Cocktail Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Shanti Art Musik Bar, which offers a similarly pleasant setting and great drinks. Another option is Gran Caffè Gambrinus, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and celebrate another amazing 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 Amalfi and Ravello to the fullest today with this curated day itinerary!

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

After visiting Amalfi Coast and Saint Andrew's Fountain Amalfi, take time to explore Naples's streets and absorb its charm. Continue your sightseeing by heading to Villa Rufolo. This enchanting historical landmark offers a unique experience.

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

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.

Savor the flavors at Antica Pizzeria Di Matteo, a top pick for dinner tonight. Alternatively, Mercure Napoli Centro Angioino beckons with its unique menu offerings. Also, consider La Lazzara Trattoria e Pizzeria. With its consistent customer satisfaction, it’s an excellent option for dining in Naples tonight.

Extend your evening after a delightful meal by visiting Archivio Storico - Cocktail Bar & Wonderfood, which offers the perfect atmosphere for a night out. Moreover, Archeobar is another popular option for a drink or two. Likewise, Babette Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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

Discover a day packed with fun adventures, breathtaking views, and photo-friendly spots in Naples. Begin your sightseeing with Archaeological Park Of Pompeii. This notable archeological site is one of the top attractions in the town. Proceed to Teatro Grande, another must-visit attraction that enhances the town’s allure.

As you wander through the inviting streets of Naples, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Amphitheatre Of Pompeii. This well-known archeological site is a traveler-favorite.

At the end of the day, you will drive to Pisa, 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 Pisa. 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 Capodimonte Pisa, a highly-rated dining destination in Pisa. If you're eager to try something different, consider La Locanda Dei Pisani Doc Pisa, another top spot with a tantalizing menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Pisa this evening.

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

Raise your glass to another unforgettable day in Italy!