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

Get ready for an exciting day in Pisa. Today’s sightseeing agenda includes a monument, a public square, a historical landmark, an art gallery and much more! Begin your adventure at Leaning Tower Of Pisa. This is a wondrous monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a world-famous public square in Pisa.

When you’re ready for the next sight, head to Ponte Vecchio. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s astonishing attractions. We recommend continuing your self-guided tour at Piazza Della Signoria, a visually striking place of interest in the city.

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

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.

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.

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.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to David. This locally renowned statue provides an insightful glimpse into the city's identity. Next, discover Galleria Dell'accademia, a standout art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Central Market, a notable food market. When you’re done, don’t forget to make a stop at the famous Cathedral Of Santa Maria Del Fiore. Not far away from the church, you will find the visually striking Piazzale Michelangelo, perfect for a quick visit. Round off your day at Basilica Of Santa Croce In Florence, another gem in Florence with culturally significant features to discover.

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.

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

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in San Gimignano. You will spend 2 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Palazzo Salimbeni is the perfect place to start. This palace is one of the most beloved places to visit in Florence. Next, head to Piazza Del Campo, a spectacular public square, known for its UNESCO world heritage-designated 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 Siena Cathedral. This romantic church is a highly recommended experience. Nearby, you'll also find Porta San Giovanni and Parco Della Rocca. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Duomo, a romantic public square in Florence.

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.

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.

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

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Castle Of Verrazzano. This often recommended castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Fattoria Viticcio, one of the town’s best highlights.

Next, check out Villa Calcinaia - Conti Capponi, one of the most worthwhile places to see in San Gimignano. This winery is a favorite among locals and travelers alike.

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

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

Savor another day of unforgettable experiences 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 adventure at Basilica Of San Francesco D'assisi. This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta San Giacomo located in San Gimignano for another exciting encounter.

Next, immerse yourself in the setting of Portico Of Monte Frumentario. Its picture-perfect features will captivate you. After the historical landmark, continue your tour of the town with a visit to Rocca Maggiore. Visitors usually appreciate the romantic features of this castle. Next up is Basilica Di Santa Chiara, a highly recommended church. For a change of pace, head to Piazza Del Comune. As one of the most often recommended attractions in San Gimignano, this public square is the perfect place to end your self-guided sightseeing tour.

At the end of the day, you will drive to Santa Maria degli Angeli, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a well-loved spot among locals and tourists.

Raise your glass to another unforgettable day in Italy!

Dive into day 7 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 fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Colosseum. This globally renowned archeological site is a picture-perfect place to see in Santa Maria degli Angeli. Continue your discovery at Roman Forum, an UNESCO world heritage-listed archeological site with stories to tell.

As you stroll around Santa Maria degli Angeli, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pantheon. This globally renowned monument offers a heritage-rich encounter with Santa Maria degli Angeli. Next, make your way to Trevi Fountain to add another highlight to your day. After that, visit Spanish Steps, an astonishing public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Di Spagna, a timeless public square 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 Santa Maria degli Angeli.

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.

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

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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.

Celebrate another amazing day of your road trip adventure 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!

Don’t miss Via del Corso 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 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 Del Popolo is an impressive 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 Piazza Navona. Take a moment to appreciate the fascinating details of this timeless public square.

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.

Enjoy a delicious meal 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.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

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

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Today’s agenda in Rome includes a monument, a church, a museum, a cave system, a cave and much more! Well Of St. Patrick is must-visit monument and a great starting point for the day. Next, continue your journey to Orvieto Cathedral, an interesting church, located just a leisurely stroll away. Next, head to Museo Dell'opera Del Duomo, a photogenic museum, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the increasingly popular Orvieto Underground. If you’re looking for more, Torre Del Moro Orvieto is also an often recommended attraction that is worthwhile a visit. Lastly, don’t miss Pozzo Della Cava, a place of photogenic interest in the village.

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.

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.

If you’re not ready to end the night just yet, Bar Mocambo offers a perfect venue to relax and savor a drink. Similarly, Tree is well-suited for those looking to unwind in a social setting. Chupiteria is another excellent spot to enjoy a nightcap after a delightful meal.

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