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

Your itinerary for day 2 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

Make time for Leaning Tower Of Pisa, an iconic monument that is worthwhile a visit in the city. Nearby, you’ll find Piazza Del Duomo, Pisa, enchanting visitors with its stunning appeal. Continue your exploration at Ponte Vecchio. This historical landmark is one of the city’s most iconic spots.

Enjoy the freedom of exploring Pisa at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Uffizi Gallery. After exploring the art gallery, head to the widely recognized Piazza Della Signoria.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight 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.

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

Day 3 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Florence is brimming with adventures.

Look forward to a unique sightseeing adventure at the captivating David and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Dell'accademia, a photogenic art gallery that draws visitors from far and near.

Continue your journey to Central Market, one of the city’s most popular spots that you shouldn’t miss. Another great site to visit is the famous Cathedral Of Santa Maria Del Fiore. When you're finished at the church, Basilica Of Santa Croce In Florence awaits your visit. This church is a photogenic highlight on today's itinerary. Last up is an observation deck - the spectacular Piazzale Michelangelo.

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.

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 Florence, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

Relax and look forward to more memorable moments to come!

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

Palazzo Salimbeni is must-visit palace and a great option for a daytime tour of the area. Continue your journey to Piazza Del Campo, a top-rated public square, located just a leisurely stroll away. Next, head to Siena Cathedral, a culturally significant church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the intriguing Porta San Giovanni. If you’re looking for more, Parco Della Rocca is also an intriguing attraction that is worthwhile a visit. Lastly, don’t miss Piazza Del Duomo, a place of symbolic interest in the city.

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.

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 San Gimignano, it's often a good idea to reserve a table in advance.

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

Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Greve in Chianti, Montefioralle, and Greti. With 1 night to stay in San Gimignano, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!

Castle Of Verrazzano makes a great addition to your morning plans. This curiosity-inducing castle is an enchanting place to see in San Gimignano. Continue your discovery at Fattoria Viticcio, a serene winery with stories to tell.

As you stroll around San Gimignano, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Villa Calcinaia - Conti Capponi. This often recommended winery offers a visually striking encounter with San Gimignano. 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.

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

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.

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

Dive into day 6 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Santa Maria degli Angeli. At the end of the day, you’ll unwind at one of the finest accommodations in Santa Maria degli Angeli, where you'll spend 1 night.

No visit to San Gimignano is complete without Basilica Of San Francesco D'assisi. This popular church is one of the top attractions in the town. Proceed to Porta San Giacomo, 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 Portico Of Monte Frumentario. This worthwhile historical landmark is a traveler-favorite. Not far away, you’ll find Rocca Maggiore, another key site on your sightseeing itinerary. Basilica Di Santa Chiara is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Comune and uncover why it's recognized as one of the town's most increasingly popular attractions.

When you’re done exploring for the day, you’ll drive to your hotel in Santa Maria degli Angeli. Check in and relax before you head out to tour the town.

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

Continue your evening by exploring the vibrant nightlife scene at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a prime destination for a thrilling night out.

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

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Rome, where you will stay for 2 nights.

Colosseum brings Santa Maria degli Angeli's character to life. This picture-perfect archeological site is a highlight of any visit in the city. Then, enjoy Roman Forum, another breathtaking attraction that never fails to captivate visitors. Next, head over to Pantheon, one of the city’s most wondrous attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Trevi Fountain. This noteworthy monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Spanish Steps, an extraordinary 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.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Don’t miss out on dining 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 enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

On day 8 of your road trip, you’ll start and end your day in Rome, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Vatican City and Rome.

Whether you decide to explore Vatican City on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Make sure to visit Via del Corso, 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.

Make a stop at Vatican Museums. This globally renowned art museum is a must-visit for travelers looking for a unique holiday experience. Make your way to St. Peter's Basilica located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Sistine Chapel. After the chapel, continue your tour of the city with a visit to Piazza Del Popolo. Visitors usually appreciate the culturally significant features of this public square. Next up is Piazza Navona, a highly recommended public square.

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

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.

Treat yourself to a delightful dinner at RomAntica, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Coso Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at DEROMA - Farine Romane as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Sant' Eustachio Caffè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yellowsquare Rome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino 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 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Orvieto. When you’re not sightseeing, take time to relax at your chosen hotel in Pisa, where you’ll be staying for 1 night.

Well Of St. Patrick makes a great addition to your morning plans. This notable monument is a culturally significant place to see in Rome. Continue your discovery at Orvieto Cathedral, a history-steeped church with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Museo Dell'opera Del Duomo. This increasingly popular museum offers a noteworthy encounter with Rome. Next, make your way to Orvieto Underground to add another highlight to your day. After that, visit Torre Del Moro Orvieto, a worthwhile monument that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Pozzo Della Cava, a curiosity-inducing cave in the village. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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 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.

Treat yourself to a delightful dinner at Ristorante Capodimonte Pisa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Locanda Dei Pisani Doc Pisa? It's another excellent option with a diverse menu. Consider reserving a table at Baribaldi Pisa as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

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.

Raise your glass to another unforgettable day in Italy!