9-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, San Gimignano, and Rome

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

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

Next, check out Pisa Cathedral, one of the most frequently visited places to see in Pisa. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Galleria Dell'accademia. Wander around and soak in the photogenic atmosphere this art gallery offers. Then, head to David, a top-rated statue that adds another dimension to your day. Finally, visit the widely recognized Cathedral Of Santa Maria Del Fiore, the last of our attraction recommendations for today.

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.

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 Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Don’t miss Oltrarno in Florence today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Today’s itinerary in Florence covers several incredible sights, including a historical landmark, an art gallery, a public square, a church, an observation deck and much more! Start your adventure at Ponte Vecchio. This world-famous historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Uffizi Gallery, a must-see art gallery 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 Piazza Della Signoria. This famous public square offers an enriching experience. For a change of pace, head to Basilica Of Santa Croce In Florence, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to 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.

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.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the 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 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 2 nights.

Start by visiting Siena Cathedral, a prime spot to begin your journey. This history-steeped church is sure to impress. Next on your list is Facciatone, another must-visit landmark and intriguing observation deck renowned for its romantic 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 Del Campo. This enchanting public square is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Parco Della Rocca, a worthwhile park. Nearby, you'll also find Palazzo Comunale, Pinacoteca, Torre Grossa, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazza Del Duomo and wrap up your day with its enchanting appeal.

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.

As you explore more of San Gimignano, 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.

As the sun sets on another day of adventure, rest up and recharge for the next leg 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 San Gimignano for your remaining 1 night in the village 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 Greve in Chianti, Montefioralle, and Greti.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in San Gimignano allows for both. Start by heading to Castle Of Verrazzano. This curiosity-inducing castle provides an insightful glimpse into the town's identity. Next, discover Fattoria Viticcio, a mesmerizing winery, promising a delightful encounter.

Continue your sightseeing with a visit to Villa Calcinaia - Conti Capponi, a locally appreciated winery.

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

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

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

Dive into day 6 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 an exciting day in San Gimignano. Today’s sightseeing agenda includes a castle, a public square, a monument, an archeological site and much more! Begin your adventure at Castel Sant'angelo. This is a widely recognized castle you should not miss. Another must-see is Piazza Navona, an iconic public square in San Gimignano.

When you’re ready for the next sight, head to Pantheon. From there, take a leisurely stroll to Trevi Fountain, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Piazza Del Popolo, a history-steeped place of interest in the city. If time allows, add Circus Maximus to your itinerary. This interesting archeological site offers the perfect finishing touch to your day in San Gimignano.

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.

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

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.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

On day 7 of your road trip, you’ll start and end your day in Rome, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Vatican City and Rome. You still have 1 night left in Rome.

Don’t miss Via dei Condotti in Vatican City today, a must-see street that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Start your adventure at Vatican Museums. This globally renowned art museum is a place that is appreciated by travelers and locals alike.

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 Sistine Chapel. This extraordinary chapel offers an enriching experience. For a change of pace, head to Piazza Di Spagna, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to Spanish Steps. These sights offer a fulfilling end to a perfect day.

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

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

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

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

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

Today’s itinerary in Rome covers several incredible sights, including a monument, a church, a museum, a cave system, a cave and much more! Start your adventure at Well Of St. Patrick. This interesting monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the majestic wonders of Orvieto Cathedral, a must-see church in the village.

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 Museo Dell'opera Del Duomo. This locally appreciated museum offers an enriching experience. For a change of pace, head to Orvieto Underground, where you can take in respected features. Conclude your self-guided sightseeing tour with a visit to Torre Del Moro Orvieto and Pozzo Della Cava. These sights offer a fulfilling end to a perfect day.

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

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Let the evening flow smoothly from dinner to drinks at Bar Mocambo, a top-rated bar in the area. For other recommendations, Tree provides a perfect setting for rounding out your night with style and great drinks. Likewise, Chupiteria offers a memorable night with diverse drink options and excellent service.

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