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

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Florence. 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 2 nights.

Today’s well-planned self-sightseeing route offers several fun adventures, breathtaking views, and picturesque spots. Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Leaning Tower Of Pisa is the first of them. Spend some time admiring this historic monument before continuing your journey. Piazza Del Duomo, Pisa is your next stop. This world-famous public square is one of the best-rated sights in Pisa.

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 Pisa Cathedral. This breathtaking church is a sight to behold. To round off your sightseeing experience, visit Galleria Dell'accademia and David. If time allows, end your day with Cathedral Of Santa Maria Del Fiore, a visually striking church that offers a memorable conclusion to your exploration.

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 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 lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 3 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Ponte Vecchio. This timeless historical landmark is a visually striking place to see in Florence. Continue your discovery at Uffizi Gallery, a picture-perfect art gallery with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Della Signoria. This impressive public square offers a detailed encounter with Florence. Next, make your way to Basilica Of Santa Croce In Florence to add another highlight to your day. After that, visit Piazzale Michelangelo, a widely recognized observation deck that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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.

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.

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.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in San Gimignano, where you’ll be staying for 2 nights.

Florence is brimming with adventures. Today’s wonderful stops include a church, an observation deck, a public square, a park, a museum and much more! Begin your sightseeing adventure at the captivating Siena Cathedral and allow yourself time to explore. Just a short distance away you'll find your next stop, Facciatone, a romantic observation deck that draws visitors from far and near.

Continue your journey to Piazza Del Campo, one of the city’s most top-rated spots that you shouldn’t miss. Another great site to visit is the increasingly popular Parco Della Rocca. When you're finished at the park, Palazzo Comunale, Pinacoteca, Torre Grossa awaits your visit. This museum is an UNESCO world heritage-designated highlight on today's itinerary. Last up is a public square - the increasingly popular 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.

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.

Head back to your accommodation in San Gimignano 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 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.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in San Gimignano. Begin your sightseeing with Castle Of Verrazzano. This increasingly popular castle is one of the top attractions in the town. Proceed to Fattoria Viticcio, another must-visit attraction.

As you wander through the inviting streets of San Gimignano, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Villa Calcinaia - Conti Capponi. This often recommended winery is a traveler-favorite.

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

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.

Say good night to San Gimignano and look forward to another great 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.

Start by visiting Castel Sant'angelo, a prime spot to begin your journey. This visually striking castle is sure to impress. Next on your list is Piazza Navona, another must-visit landmark and wondrous public square renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of San Gimignano by sampling some local delicacies. When you’re ready for more sightseeing, head to Pantheon. This instagrammable monument is an essential place to visit for anyone looking for the full San Gimignano experience. We also recommend visiting Trevi Fountain, a wondrous monument. Nearby, you'll also find Piazza Del Popolo, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Circus Maximus and wrap up your day with its standout appeal.

At the end of the day, you will drive to Rome, 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 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.

Enjoy a delicious meal at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to La Botticella Of Poggi Giovanni, known for its inviting atmosphere. Almalu Trastevere is another great option if you’re looking for a place to get the night started. Similarly, Bar Viminale Di Pepi Maurilio provides a great setting to enjoy the night away.

Savor another day of unforgettable experiences in Italy!

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

Make sure to visit Via dei Condotti, a popular street in Vatican City. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

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

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 world-famous spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the visually striking Spanish Steps. Take a moment to appreciate the fascinating details of this top-rated public square.

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.

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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.

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

On day 8 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 Orvieto. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

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 notable monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped 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 underrated museum offers an enriching experience. For a change of pace, head to Orvieto Underground, where you can take in instagrammable 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.

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

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.

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.

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.