10-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, San Gimignano, Santa Maria degli Angeli, and Rome

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 2 places, which are Pisa and Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

Experience Leaning Tower Of Pisa, an iconic monument in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this breathtaking public square.

There are many interesting places to see in Pisa, and when you are ready for more, go to Ponte Vecchio. This is one of the city’s most globally renowned enchanting spots of interest. After exploring the historical landmark, visit the extraordinary Uffizi Gallery. Not far away, you'll also find Piazza Della Signoria. This public square is a history-steeped highlight in Pisa.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Savor another day of unforgettable experiences in Italy!

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Florence.

Florence is brimming with adventures.

David leaves a lasting impression. This statue is one of the most captivating places to visit in Florence. Next, head to Galleria Dell'accademia, a popular art gallery, known for its heritage-rich features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Central Market. This photogenic food market is a highly recommended experience. Nearby, you'll also find Cathedral Of Santa Maria Del Fiore and Basilica Of Santa Croce In Florence. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazzale Michelangelo, a romantic observation deck in Florence.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Enjoy a lovely dining experience at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Siena and San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in San Gimignano, where you'll spend 2 nights.

Your adventure in Florence is only getting started when you visit Palazzo Salimbeni, a curiosity-inducing local hot spot. Another notable attraction to explore is Piazza Del Campo. This top-rated public square is known for its instagrammable appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Siena Cathedral. This culturally significant church offers a fascinating experience that many visitors find memorable. Porta San Giovanni is also worth visiting, along with Parco Della Rocca. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Del Duomo. This locally appreciated public square provides a fitting finale to your sightseeing.

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.

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.

Known for great service, it’s a fantastic choice for tonight in San Gimignano.

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

On day 5 of your road trip, you’ll start and end your day in San Gimignano, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate village, including Greve in Chianti, Montefioralle, and Greti.

One of the most locally appreciated attractions included on the itinerary is Castle Of Verrazzano. This romantic castle will help you start your sightseeing on top. Then, take a leisurely stroll to Fattoria Viticcio and learn what makes this stunning winery unique.

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

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

San Gimignano is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in San Gimignano.

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

On day 6 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Santa Maria degli Angeli are on today's agenda. In the evening, you’ll end up in Santa Maria degli Angeli, where you will stay for 1 night.

Basilica Of San Francesco D'assisi brings San Gimignano's character to life. This historic church is a highlight of any visit in the town. Next, head over to Portico Of Monte Frumentario, one of the town’s most up-and-coming attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Rocca Maggiore. This visually striking castle is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Basilica Di Santa Chiara, a frequently visited church, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Comune before you head back to your hotel.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Santa Maria degli Angeli. Enjoy a relaxing evening as you savor delicious local cuisine.

Keep the excitement of the evening going by visiting a bar or two. Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings is an excellent place to start.

Say good night to Santa Maria degli Angeli and look forward to another great day of your road trip in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Rome, where you’ll be staying for 2 nights.

Look forward to a unique sightseeing adventure at the wondrous Colosseum and allow yourself time to explore. Just a short distance away you'll find your next stop, Roman Forum, a culturally significant archeological site that draws visitors from far and near.

Continue your journey to Pantheon, one of the city’s most wondrous spots that you shouldn’t miss. Another great site to visit is the iconic Trevi Fountain. When you're finished at the monument, Spanish Steps awaits your visit. This public square is a visually striking highlight on today's itinerary. Last up is a public square - the globally renowned Piazza Di Spagna.

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

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

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.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Relax and look forward to more memorable moments to come!

On day 8 of your road trip, you'll get the chance to experience Vatican City and Rome. At the end of the day, you'll drive back to Rome, where you still have 1 night left to stay.

Set aside time today to explore Via del Corso, a standout street that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Look forward to a unique sightseeing adventure at the world-famous Vatican Museums and allow yourself time to explore.

Continue your journey to Sistine Chapel, one of the city’s most impressive spots that you shouldn’t miss. Another great site to visit is the extraordinary Piazza Del Popolo. When you're finished at the public square, Piazza Navona awaits your visit. This public square is a remarkable highlight on today's itinerary.

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

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

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.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, 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!

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Pisa, where you'll spend 1 night.

To truly experience Rome, make sure to drop by Well Of St. Patrick. This captivating monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Orvieto Cathedral, one of the village’s best highlights.

Next, check out Museo Dell'opera Del Duomo, one of the most up-and-coming places to see in Rome. This museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Orvieto Underground. Wander around and soak in the eye-catching atmosphere this cave system offers. Then, head to Torre Del Moro Orvieto, a top-rated monument that adds another dimension to your day. Finally, visit the frequently visited Pozzo Della Cava, the last of our attraction recommendations for today.

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. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Mocambo, a well-loved spot among locals and tourists. Or, head to Tree. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Chupiteria, another top-rated place in the area.

Head back to your accommodation in Pisa and get some rest to prepare for another magical day of your road trip in Italy.