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, scenic views, and photo-friendly spots in the charming city of Pisa. Your adventure starts at Leaning Tower Of Pisa, a world-famous local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This globally renowned public square is known for its breathtaking 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 stunning 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 top-rated 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.

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 Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice 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.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Day 3 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Florence is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Ponte Vecchio, a timeless historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its romantic appeal. Continue your exploration at Piazza Della Signoria. This public square is one of the city’s most impressive 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 Basilica Of Santa Croce In Florence. After exploring the church, head to the famous 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.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and recharge in preparation for another adventurous 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.

Get ready to discover some of the most iconic wonders in Florence, including a church, an observation deck, a public square, a park, a museum and much more! Start your day at Siena Cathedral. This symbolic church is an interesting place to see in Florence. Then, wander over to Facciatone. If history-steeped sites excite you, this observation deck will be right up your alley. Nearby, you’ll also find Piazza Del Campo. This romantic public square is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Parco Della Rocca is a frequently visited spot in the city that will captivate you with its unique charm. When you’re done at the park, don’t forget to check out the historic Palazzo Comunale, Pinacoteca, Torre Grossa. Take a moment to appreciate the fascinating details of this curiosity-inducing museum. Wrap up your self-guided tour of Florence's top attractions with a visit to Piazza Del Duomo.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in San Gimignano. San Gimignano 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 San Gimignano's best restaurants.

With its reputation for pleasing customers, it’s a fantastic choice for tonight in San Gimignano.

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

Wake up to day 5 of your extraordinary road trip in Italy. With 1 night left in San Gimignano, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!

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

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the increasingly popular 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 reminisce about your day in Italy and look forward to more memorable moments to come!

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 Rome. In the evening, you’ll end up in Rome, where you will stay for 2 nights.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Castel Sant'angelo. This top-rated castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Navona, one of the city’s best highlights.

Next, check out Pantheon, one of the most world-famous places to see in San Gimignano. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Trevi Fountain. Wander around and soak in the enchanting atmosphere this monument offers. Then, head to Piazza Del Popolo, a top-rated public square that adds another dimension to your day. Finally, visit the popular Circus Maximus, the last of our attraction recommendations for today.

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.

Enjoy a delicious meal at La Bottega Roma, a highly-rated dining destination in Rome. If you're eager to try something different, consider Pasta In Corso, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s an excellent 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.

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

On day 7 of your road trip, you’ll start and end your day in Rome, where you'll stay for 1 night more.

One of the most iconic places you can visit today in Vatican City is Via dei Condotti. Allow yourself some time to explore this street and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Start your adventure 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 Di Spagna. Visitors usually appreciate the enchanting features of this public square. Next up is Spanish Steps, a highly recommended public square.

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

As you explore more of Rome, 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.

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.

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.

Raise your glass to another unforgettable day in Italy!

On day 8 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.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly spots. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Well Of St. Patrick is the first of them. Spend some time admiring this culturally significant monument before continuing your journey. Orvieto Cathedral is your next stop. This notable church is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Museo Dell'opera Del Duomo. This noteworthy museum is a sight to behold. To round off your sightseeing experience, visit Orvieto Underground and Torre Del Moro Orvieto. If time allows, end your day with Pozzo Della Cava, a photogenic cave that offers a memorable conclusion to your exploration.

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 in Pisa. 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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Mocambo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Tree offers an ideal atmosphere to enjoy the pleasures of the night. Chupiteria is also a great option that provides a perfect setting for a relaxing evening.

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