12-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Siena, 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 3 nights.

No visit to Pisa is complete without Knights' Square. This up-and-coming public square is one of the top attractions in the city. Proceed to Leaning Tower Of Pisa, another must-visit attraction.

As you wander through the inviting streets of Pisa, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Del Duomo, Pisa. This iconic public square is a traveler-favorite. Not far away, you’ll find Campo Santo, another key site on your sightseeing itinerary.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Florence may take around 1 hour 16 min. Upon your arrival in Florence, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Savor the day by heading to Galleria Dell'accademia, a popular art gallery that draws visitors from near and far. When you're done, continue to Cathedral Of Santa Maria Del Fiore, where you can soak in the inviting surroundings.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

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.

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

Day 3 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

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.

No visit to Florence is complete without Piazzale Michelangelo. This extraordinary observation deck is one of the top attractions in the city. Proceed to Basilica Of Santa Croce In Florence, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Della Signoria. This astonishing public square is a traveler-favorite. Not far away, you’ll find Uffizi Gallery, another key site on your sightseeing itinerary. Ponte Vecchio is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

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

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.

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

On day 4 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Set your GPS to Greve in Chianti and hit the road. Expect a journey of approximately 46 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greve in Chianti beckons with new experiences!

Our first attraction recommendation in Greve in Chianti is Castle Of Verrazzano, a worthwhile castle that draws attention for its romantic features.

Fasten your seatbelt and make your way to your next stop — Castellina in Chianti, home to many well-known sights in the region. Keep in mind that your travel time from Greve in Chianti to Castellina in Chianti may take around 37 min without traffic disruptions. Upon arrival in Castellina in Chianti, we highly recommend checking out some of the top attractions.

For a more meaningful self-guided tour of the town's best attractions, visit Tumulo Di Montecalvario, a locally appreciated archeological site 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 Rocca Di Castellina In Chianti and admire its history-steeped features.

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

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

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Gosh*, a well-loved spot among locals and tourists. Or, head to Antico Caffè Del Moro - Art Bar Firenze. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Quelo Bar, another top-rated place in the area.

Raise your glass to another unforgettable day in Italy!

On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 3 nights.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 12 min.

Set out on a self-guided sightseeing tour at Siena Cathedral and explore the culturally significant features. Next, make your way to Pubblico Palace, another highlight in Siena. When you’re done exploring the palace, continue to Piazza Del Campo, an enchanting public square.

Nearby, you will also find Tower Of Mangia. This frequently visited monument is a top place to see in the area.

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 wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

On day 6 of your road trip, you’ll start and end your day in Siena, where you still have 2 nights left. You'll spend part of the day exploring places of interest outside the immediate city, including San Gimignano.

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

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to San Gimignano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 45 min. Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Rocca Di Montestaffoli is a beloved castle we recommend visiting today. Discover its history-steeped features before continuing your self-guided tour to Palazzo Comunale, Pinacoteca, Torre Grossa, an UNESCO world heritage-designated museum that’s well-regarded in the area.

Next, stop by Piazza Del Duomo, a visually striking public square.

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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pinacoteca, a bar catering to every mood and preference. San Paolo Pub likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Greet day 7 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Siena, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Castelnuovo dell'Abate, Montalcino, Pienza, and Castiglione d'Orcia.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Castelnuovo dell'Abate. This drive usually takes around 1 hour 4 min.

Savor the day by heading to Abbey Of Sant'antimo, an increasingly popular monastery that draws visitors from near and far.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Montalcino. This drive usually takes around 12 min, without any stops or traffic disruptions.

Our first attraction recommendation in Montalcino is Fortress Of Montalcino, an intriguing castle that draws attention for its romantic features.

Set your GPS to Pienza and hit the road. Expect a journey of approximately 29 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pienza beckons with new experiences!

Palazzo Piccolomini, Pienza is a locally appreciated palace we recommend visiting today. Discover its romantic features before continuing your self-guided tour.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

Make sure to reserve a table at Ristorante San Desiderio, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Le Logge, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Taverna Di Cecco, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 2 hours 38 min, without any stops or traffic disruptions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Villa Borghese, a top-rated park that everyone visiting Rome should see. Next, head to Spanish Steps. This majestic public square is one of the most spectacular attractions in the region.

If you're keen to see more, don’t miss out on Piazza Di Spagna, a romantic public square popular among locals as well as travelers. Trevi Fountain is an excellent attraction to visit next. Spend some time learning more about this timeless monument before you continue your journey. Lastly, visit Pantheon, a monumental monument and a top attraction in the city.

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.

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 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. Known for great service, it’s a fantastic choice for tonight in Rome.

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.

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

Day 10 offers an itinerary packed with the best things to see in Pisa. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Whatever your travel style is, Colosseum is an essential stop in Rome. This globally renowned archeological site provides an insightful glimpse into the city's identity. Next, discover Arch Of Constantine, a culturally significant monument, promising a delightful encounter.

Continue your sightseeing with a visit to Roman Forum, an iconic archeological site. When you’re done, don’t forget to make a stop at the spectacular Campo De' Fiori. Not far away from the public square, you will find the majestic Castel Sant'angelo, perfect for a quick visit. Round off your day at Piazza Navona, another gem in Rome with romantic features to discover.

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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

After savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

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

On day 11 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.

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!

Savor the day by heading to Orvieto Cathedral, an interesting church that draws visitors from near and far. When you're done, continue to Orvieto Underground, where you can soak in the heritage-rich surroundings.

Next, explore Torre Del Moro Orvieto, yet another up-and-coming place to see in the area. After the monument, make time to go to Pozzo Della Cava. This heritage-rich cave is well worth the visit.

When you’re done exploring for the day, you’ll drive to your hotel in Pisa. Check in and relax before you head out to tour the city.

Pisa 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 Pisa.

Don’t miss out on dining at Ristorante Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider La Locanda Dei Pisani Doc Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Cap off your dinner by heading to Bar Mocambo, ideal for a leisurely evening with a drink in hand. Tree is another bar that offers an enjoyable setting. Similarly, Chupiteria is also a popular place to go on a night out, perfect for relaxing and socializing.

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