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 vibrant destinations - Pisa and Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Pisa. Some of the city’s most loved attractions await! Leaning Tower Of Pisa is the perfect place to start. This monument is one of the most iconic places to visit in Pisa. Next, head to Piazza Del Duomo, Pisa, a timeless public square, known for its historic 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 Ponte Vecchio. This visually striking historical landmark is a highly recommended experience. Nearby, you'll also find Uffizi Gallery and Piazza Della Signoria. Visit these for an interesting touch to your journey.

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.

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 Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

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

On day 3 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Florence is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and historic treasures! Start at David, a locally renowned statue that is worthwhile a visit in the city. Nearby, you’ll find Galleria Dell'accademia, enchanting visitors with its detailed appeal. Continue your exploration at Central Market. This food market is one of the city’s most notable spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Cathedral Of Santa Maria Del Fiore. After exploring the church, head to the well-known Basilica Of Santa Croce In Florence. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazzale Michelangelo, a place of enchanting interest 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.

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 meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 will explore Siena and San Gimignano, 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 San Gimignano. You’ll stay here for 2 nights.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a palace, a public square, a church, a monument, a park and much more! Begin your adventure at Palazzo Salimbeni. This is an often recommended palace you should not miss. Another must-see is Piazza Del Campo, a spectacular public square in Florence.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Porta San Giovanni, another of the city’s up-and-coming attractions. We recommend continuing your self-guided tour at Parco Della Rocca, a romantic place of interest in the city. If time allows, add Piazza Del Duomo to your itinerary. This frequently visited public square offers the perfect finishing touch to your day in Florence.

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

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

On day 5 of your road trip, you’ll start and end your day in San Gimignano, where you'll stay for 1 night more.

Start by visiting Castle Of Verrazzano, a prime spot to begin your journey. This romantic castle is sure to impress. Next on your list is Fattoria Viticcio, another must-visit landmark and increasingly popular winery renowned for its eye-catching 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 Villa Calcinaia - Conti Capponi. This history-steeped winery is an essential place to visit for anyone looking for the full San Gimignano experience.

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

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.

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

On day 6 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 Santa Maria degli Angeli, where you will stay for 1 night.

Start your day with a visit to Basilica Of San Francesco D'assisi. This notable church is a must-visit in the town.

One of the best things about exploring San Gimignano 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 Portico Of Monte Frumentario, a curiosity-inducing historical landmark in the town. If you’re up for more discoveries, don’t forget to reserve some time for Rocca Maggiore and Basilica Di Santa Chiara. End your day with a visit to Piazza Del Comune, an underrated public square that’s sure to leave a lasting impression.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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 dinnertime approaches, it's time to head out for a bite to eat in Santa Maria degli Angeli. If you are looking to dine at a popular restaurant in the town, it's often a good idea to reserve a table in advance.

Following your dinner, dive into the local bar culture at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings. Enjoy this evening's relaxed ambiance with delightful drinks.

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 2 nights.

Today's adventure in Santa Maria degli Angeli promises more breathtaking discoveries and enriching experiences! Begin at Colosseum. This culturally significant archeological site is a highlight of any visit in the city. Then, enjoy Roman Forum, another historic attraction that never fails to captivate visitors. Next, head over to Pantheon, one of the city’s most timeless attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Trevi Fountain. This visually striking monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Spanish Steps, a widely recognized public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Di Spagna before you head back to your hotel.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences in Italy!

On day 8 of your road trip in Italy, you’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 1 night more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

A top thing to do today is to explore Via del Corso, a must-see street in Vatican City. It's the perfect starting point for touring the top attractions in the area.

Start your day with a visit to Vatican Museums. This wondrous art museum is a must-visit in the city.

One of the best things about exploring Rome 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 Sistine Chapel, a spectacular chapel in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Del Popolo and Piazza Navona.

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

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

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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.

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Orvieto. When you’re not sightseeing, take time to relax at your selected hotel in Pisa, where you’ll be staying for 1 night.

Savor the day by visiting some of the best places to see in Rome, including a monument, a church, a museum, a cave system, a cave and much more! Start your adventure at Well Of St. Patrick. This popular monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Orvieto Cathedral located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Museo Dell'opera Del Duomo. Its noteworthy features will captivate you. After the museum, continue your tour of the village with a visit to Orvieto Underground. Visitors usually appreciate the heritage-rich features of this cave system. Next up is Torre Del Moro Orvieto, a highly recommended monument. For a change of pace, head to Pozzo Della Cava. As one of the most locally appreciated attractions in Rome, this cave is the perfect place to end your self-guided sightseeing tour.

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.

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

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.

To truly maximize your evening out, consider visiting Bar Mocambo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Tree, another bar with an inviting ambiance. Similarly, Chupiteria also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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