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.

Get ready for a day filled with fun adventures, breathtaking views, and photo-friendly spots in the charming city of Pisa. Your adventure starts at Leaning Tower Of Pisa, a timeless local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This globally renowned public square is known for its historic appeal.

After soaking in the highlights of these sights, take some time to wander Pisa's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Pisa Cathedral. This picture-perfect church offers a fascinating experience that many visitors find memorable. Galleria Dell'accademia is also worth visiting, along with David. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Cathedral Of Santa Maria Del Fiore. This spectacular church provides a fitting finale to your sightseeing.

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.

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.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

Celebrate another amazing day of your road trip adventure 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.

Oltrarno is a fantastic place you can explore today in Florence. 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 Florence-way-of-life and visit all the nearby sights.

Today, you'll explore some of the most beautiful places in Florence, including a historical landmark, an art gallery, a public square, a church, an observation deck and much more! Start your day with a visit to Ponte Vecchio. This iconic historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Uffizi Gallery, which may be one of the most standout places you will experience today.

One of the best things about exploring Florence 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 Piazza Della Signoria, an extraordinary public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of Santa Croce In Florence and Piazzale Michelangelo.

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 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.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery 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!

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.

Today, you'll explore some of the most beautiful places in Florence, including a church, an observation deck, a public square, a park, a museum and much more! Start your day with a visit to Siena Cathedral. This well-known church is a must-visit in the city. When you’re ready for your next discovery, continue to Facciatone, which may be one of the most symbolic places you will experience today.

One of the best things about exploring Florence 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 Piazza Del Campo, a widely recognized public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Parco Della Rocca and Palazzo Comunale, Pinacoteca, Torre Grossa. End your day with a visit to Piazza Del Duomo, a beloved public square that’s sure to leave a lasting impression.

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

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

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

Enjoy the perfect balance of relaxation and exploration in San Gimignano today. One of the most underrated attractions included on the itinerary is Castle Of Verrazzano. This instagrammable castle will help you start your sightseeing on top. Then, take a leisurely stroll to Fattoria Viticcio and learn what makes this mesmerizing winery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Villa Calcinaia - Conti Capponi.

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

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.

Relax and recharge in preparation for another adventurous day 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.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Castel Sant'angelo. This spectacular castle is a majestic place to see in San Gimignano. Continue your discovery at Piazza Navona, a remarkable public square with stories to tell.

As you stroll around San Gimignano, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pantheon. This world-famous monument offers a photogenic encounter with San Gimignano. Next, make your way to Trevi Fountain to add another highlight to your day. After that, visit Piazza Del Popolo, an extraordinary public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Circus Maximus, a locally renowned archeological site in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in San Gimignano.

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.

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

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.

Raise your glass to another unforgettable day in Italy!

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

Via dei Condotti is a fantastic place you can explore today in Vatican City. This street 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.

Begin your adventure at Vatican Museums. This is a globally renowned art museum you should not miss. Another must-see is St. Peter's Basilica, a globally renowned major basilica in Rome.

When you’re ready for the next sight, head to Sistine Chapel. From there, take a leisurely stroll to Piazza Di Spagna, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Spanish Steps, an enchanting place of interest in the city.

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

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

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.

Round off your dining experience by visiting Sant' Eustachio Caffè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yellowsquare Rome, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

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

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.

Start by visiting Well Of St. Patrick, a prime spot to begin your journey. This historic monument is sure to impress. Next on your list is Orvieto Cathedral, another must-visit landmark and well-known church renowned for its romantic features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Museo Dell'opera Del Duomo. This heritage-rich museum is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Orvieto Underground, an underrated cave system. Nearby, you'll also find Torre Del Moro Orvieto, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Pozzo Della Cava and wrap up your day with its historic appeal.

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 explore more of Pisa, 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 Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider La Locanda Dei Pisani Doc Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

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