12-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Siena, and Rome

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Pisa and Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 3 nights.

Your adventure in Pisa is only getting started when you visit Knights' Square, an often recommended local hot spot. Another notable attraction to explore is Leaning Tower Of Pisa. This timeless monument is known for its historic 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 Piazza Del Duomo, Pisa. This symbolic public square offers a fascinating experience that many visitors find memorable. Campo Santo is also worth visiting.

Fasten your seatbelt and make your way to your next stop — Florence, home to many well-known sights in the region. Keep in mind that your travel time from Pisa to Florence may take around 1 hour 16 min without traffic disruptions. Upon arrival in Florence, we highly recommend checking out some of the top attractions.

For a more meaningful self-guided tour of the city's best attractions, visit Galleria Dell'accademia, a popular art gallery that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Cathedral Of Santa Maria Del Fiore and admire its UNESCO world heritage-designated features.

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.

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.

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.

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 to prepare for another magical day of your road trip in Italy.

On day 3 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 2 nights.

Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Visiting Piazzale Michelangelo is always a good idea. This impressive observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the heritage-rich wonders of Basilica Of Santa Croce In Florence, a must-see church in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Piazza Della Signoria. This top-rated public square offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in historic features. Conclude your self-guided sightseeing tour with a visit to Ponte Vecchio These sights offer a fulfilling end to a perfect day.

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 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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day in Italy!

On day 4 of your road trip, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Greve in Chianti and Castellina in Chianti.

Whether you decide to explore Greve in Chianti on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Greve in Chianti may take around 46 min. Upon your arrival in Greve in Chianti, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castle Of Verrazzano, an often recommended castle that everyone visiting Greve in Chianti should see.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Castellina in Chianti may take around 37 min. Upon your arrival in Castellina in Chianti, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Savor the day by heading to Tumulo Di Montecalvario, a beloved archeological site that draws visitors from near and far. When you're done, continue to Rocca Di Castellina In Chianti, where you can soak in the romantic surroundings.

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

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. Known for great service, it’s a fantastic choice for tonight in Florence.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar 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!

Dive into day 5 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Siena. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 3 nights.

Fasten your seatbelt and make your way to your next stop — Siena, home to many well-known sights in the region. Keep in mind that your travel time from Florence to Siena may take around 1 hour 12 min without traffic disruptions. Upon arrival in Siena, we highly recommend checking out some of the top attractions.

Savor the day by heading to Siena Cathedral, an interesting church that draws visitors from near and far. When you're done, continue to Pubblico Palace, where you can soak in the picture-perfect surroundings.

Next, explore Piazza Del Campo, yet another widely recognized place to see in the area. After the public square, make time to go to Tower Of Mangia. This picture-perfect monument is well worth the visit.

At the end of the day, you will drive to Siena, 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 Siena's best restaurants.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. Known for great service, it’s a fantastic choice for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of San Gimignano. With 2 nights to stay in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Set your GPS to San Gimignano and hit the road. Expect a journey of approximately 45 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Our first attraction recommendation in San Gimignano is Rocca Di Montestaffoli, an up-and-coming castle that draws attention for its visually striking features. Spend some time soaking in the atmosphere before continuing to Palazzo Comunale, Pinacoteca, Torre Grossa, an UNESCO world heritage-designated museum that stands out in the village.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Piazza Del Duomo, a beloved public square that offers a unique experience.

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

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

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

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

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

On day 7 of your road trip, you’ll start and end your day in Siena, where you have 1 night left to stay.

Castelnuovo dell'Abate is brimming with adventures.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Castelnuovo dell'Abate. Your travel time is around 1 hour 4 min.

For a more meaningful self-guided tour of the village's best attractions, visit Abbey Of Sant'antimo, an often recommended monastery that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’ve had your share of Castelnuovo dell'Abate, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Montalcino. Your travel time is around 12 min.

One of our top recommendations for your sightseeing is Fortress Of Montalcino. Spend some time admiring the culturally significant features of the castle before you continue to your next stop.

When you’ve had your share of Montalcino, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pienza. Your travel time is around 29 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Palazzo Piccolomini, Pienza, an increasingly popular palace that everyone visiting Pienza should see.

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

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

Enjoy a lovely meal at Ristorante San Desiderio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Le Logge is another top choice with a popular menu. You could also check for a table at Ristorante Taverna Di Cecco. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 3 nights.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Rome. Your travel time is around 2 hours 38 min.

Spend your afternoon discovering Villa Borghese, a widely recognized park known for its serene features. Next, continue your sightseeing at Spanish Steps, an impressive public square.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Di Spagna and uncover the details of this enchanting public square. Make sure to also explore Trevi Fountain, a globally renowned monument. For your last stop, consider Pantheon, a photogenic monument that many travelers find worth the detour.

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.

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

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.

Round off your dining experience by visiting La Botticella Of Poggi Giovanni, a prime location for a drink. Alternatively, explore the distinctive characteristics of Almalu Trastevere, a bar catering to every mood and preference. Bar Viminale Di Pepi Maurilio likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Rome.

Colosseum leaves a lasting impression. This archeological site is one of the most iconic places to visit in Rome. Next, head to Arch Of Constantine, an intriguing monument, 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 Roman Forum. This picture-perfect archeological site is a highly recommended experience. Nearby, you'll also find Campo De' Fiori and Piazza Navona Visit these for an interesting touch to your journey. Finish the day with a visit to Castel Sant'angelo, a culturally significant castle in Rome.

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

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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

On day 11 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Orvieto are on today's agenda. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Set your GPS to Orvieto and hit the road. Expect a journey of approximately 1 hour 38 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Orvieto beckons with new experiences!

Set out on a self-guided sightseeing tour at Orvieto Cathedral and explore the symbolic features. Next, make your way to Orvieto Underground, another highlight in Orvieto. When you’re done exploring the cave system, continue to Torre Del Moro Orvieto, a breathtaking monument.

Nearby, you will also find Pozzo Della Cava. This worthwhile cave is a top place to see in the area.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Pisa. Pisa 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. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Ristorante Capodimonte Pisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Locanda Dei Pisani Doc Pisa offers an enticing alternative with its varied menu. Additionally, Baribaldi Pisa is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

After your meal, keep the night alive at a bar like Bar Mocambo, known for its lively atmosphere. Tree is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Chupiteria offers an excellent atmosphere for those looking to amp up the evening.

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