10-Day Italy Self-Drive Road Trip With Itinerary from Florence to Lucca, Monterosso al Mare, Siena, Volterra, Cortona, and Pienza and surrounding area

Day 2 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Start by visiting Basilica Of Santa Croce In Florence, a prime spot to begin your journey. This heritage-rich church is sure to impress. Next on your list is Galleria Dell'accademia, another must-visit landmark and interesting art gallery renowned for its respected features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Cathedral Of Santa Maria Del Fiore. This visually striking church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Basilica Di Santa Maria Novella, Firenze (fi), a notable church.

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 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 and reflect on the day's adventures.

Don’t miss out on dining 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.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Lucca. When you’re not sightseeing, take time to relax at your selected hotel in Lucca, where you’ll be staying for 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, a public square, and a monument. Begin your adventure at Pisa Cathedral. This is an up-and-coming church you should not miss. Another must-see is Piazza Del Duomo, Pisa, a wondrous public square in Florence.

When you’re ready for the next sight, head to Leaning Tower Of Pisa. From there, take a leisurely stroll to Guinigi Tower, another of the city’s up-and-coming attractions. We recommend continuing your self-guided tour at Piazza Dell'anfiteatro, a stunning place of interest in the city.

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

Enjoy a delicious meal at Gli Orti di Via Elisa, a highly-rated dining destination in Lucca. If you're eager to try something different, consider Bar Caffè Ristretto, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Schiaffino. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Lucca this evening.

After savoring a delicious meal, step into the vibrant nightlife at Lebowski - Cocktail Bar, where the evening is just getting started. In the same way, Blend offers a unique charm perfect for experiencing the local bar scene in Lucca. Franklin'33 is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Corniglia and Monterosso al Mare. At the end of the day, you will enjoy the comforts of a top-rated hotel in Monterosso al Mare, which will be your home away from home for 1 night.

Bring your curiosity for today’s adventure around Lucca. Some of the village’s most loved attractions await! Cinque Terre National Park is the perfect place to start. This national park is one of the most interesting places to visit in Lucca. Next, head to Convent Of The Capuchin Friars, a curiosity-inducing church, known for its enchanting 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 Parrocchia Di S. Giovanni Battista. This culturally significant church is a highly recommended experience. Visit these for an interesting touch to your journey.

When you’re done exploring for the day, you’ll drive to your hotel in Monterosso al Mare. Check in and spend some time relaxing before you head out to tour the village.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Monterosso al Mare. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Pizzeria La Smorfia, a popular restaurant in Monterosso al Mare. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Monterosso al Mare at La Taverna di Monterosso, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Hotel Albergo Degli Amici. It’s yet another ideal choice to enhance your time in Monterosso al Mare tonight.

Keep the excitement of the evening going by visiting a bar or two. Enoteca Da Eliseo is an excellent place to start.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Set out on a day brimming with family-friendly attractions, scenic views, and photo-friendly spots. Start at the often recommended Fortezza Medicea (siena), a historic monument in Monterosso al Mare. Next, go to Siena Cathedral.

After visiting Fortezza Medicea (siena) and Siena Cathedral, have a stroll along Monterosso al Mare's streets and take in the local charm. Continue your sightseeing by heading to Facciatone. This history-steeped observation deck offers a unique experience. Piazza Del Campo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Tower Of Mangia, one of the most historic places to visit in Monterosso al Mare.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore San Gimignano and Volterra, 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 Volterra. You’ll stay here for 1 night.

Savor the day by visiting some of the best places to see in Siena, including a monument, a public square, a museum, a park, an archeological site and much more! Start your adventure at Porta San Giovanni. This frequently visited monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Duomo located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Palazzo Comunale, Pinacoteca, Torre Grossa. Its historic features will captivate you. After the museum, continue your tour of the village with a visit to Parco Della Rocca. Visitors usually appreciate the awe-inspiring features of this park. Next up is Parco Archeologico "enrico Fiumi", a highly recommended archeological site.

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

As you explore more of Volterra, 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.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Montepulciano and Pienza. When you’re not sightseeing, take time to relax at your selected hotel in Pienza, where you’ll be staying for 1 night.

Today's adventure in Cortona promises more breathtaking discoveries and enriching experiences! Begin at Az. Agr. Crociani Susanna Crociani. This eye-catching winery is a highlight of any visit in the town. Then, enjoy Fortezza Medicea, another history-steeped attraction that never fails to captivate visitors. Next, head over to Palazzo Piccolomini, Pienza, one of the town’s most often recommended attractions, known for its visually striking features.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Pienza. Pienza 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 in Pienza. 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!