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 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Basilica Of Santa Croce In Florence. This inviting church is a highlight of any visit in the city. Then, enjoy Galleria Dell'accademia, another photogenic attraction that never fails to captivate visitors. Next, head over to Cathedral Of Santa Maria Del Fiore, one of the city’s most famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Di Santa Maria Novella, Firenze (fi). This history-steeped church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

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

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

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass and celebrate another amazing day of your road trip 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.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 15 min. When you arrive, enjoy some sightseeing.

Your self-guided tour starts at Pisa Cathedral, an often recommended church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey. Next, head to Piazza Del Duomo, Pisa and admire its UNESCO world heritage-designated features. When you’re ready, continue to Leaning Tower Of Pisa, a world-famous monument beloved by locals and tourists alike.

As you’ve unraveled the marvels of Pisa, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Lucca may take around 32 min. Upon your arrival in Lucca, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Take your self-guided tour to Guinigi Tower, an underrated monument that everyone visiting Lucca should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Next, head to Piazza Dell'anfiteatro. This enchanting public square is one of the most popular attractions in the region.

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.

Savor the flavors at Gli Orti di Via Elisa, a top pick for dinner tonight. Alternatively, Bar Caffè Ristretto beckons with its unique menu offerings. Also, consider Ristorante Schiaffino. With its consistent customer satisfaction, it’s an excellent option for dining in Lucca tonight.

After your meal, keep the night alive at a bar like Lebowski - Cocktail Bar, known for its lively atmosphere. Blend is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Franklin'33 offers an excellent atmosphere for those looking to amp up the evening.

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

On day 4 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 Corniglia and Monterosso al Mare. In the evening, you’ll end up in Monterosso al Mare, where you will stay for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Corniglia allows for both.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Corniglia. This drive usually takes around 1 hour 31 min, without any stops or traffic disruptions.

Savor the rest of your day by heading to Cinque Terre National Park, a locally renowned national park that draws visitors from near and far.

When you’re ready to jump back into the car and say goodbye to Corniglia, you’ll hit the road in the direction of Monterosso al Mare. This drive usually takes around 28 min. When you arrive, enjoy some sightseeing.

Head to Convent Of The Capuchin Friars, a frequently visited church in Monterosso al Mare. Explore its enchanting features at your own pace before you continue your journey to your next sight, Parrocchia Di S. Giovanni Battista. This often recommended church is a top recommendation in the area.

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 explore more of Monterosso al Mare, 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.

Make sure to reserve a table at Pizzeria La Smorfia, an iconic dining spot in Monterosso al Mare. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Taverna di Monterosso, a popular restaurant in Monterosso al Mare. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Hotel Albergo Degli Amici, a hidden gem nestled in Monterosso al Mare. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Unwind after your meal by stepping into Enoteca Da Eliseo. This venue is celebrated for its extensive drink selections and cozy vibes.

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

After soaking in Monterosso al Mare’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 3 hours 2 min. When you arrive in Siena, it's time to take a break from the road.

Spend your afternoon discovering Fortezza Medicea (siena), an increasingly popular monument known for its culturally significant features. After taking in the atmosphere, continue to Siena Cathedral, a well-known church that is a must-see for anyone visiting the region. Next, stop by Facciatone and uncover the details of this visually striking observation deck. Make sure to also explore Piazza Del Campo, a top-rated public square that offers a unique experience. For your last stop, consider Tower Of Mangia, an awe-inspiring monument that many travelers find worth the detour.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Siena. Siena offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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.

Don’t miss out on dining 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.

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.

Relax and recharge in preparation for another adventurous day 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.

As you’ve unraveled the marvels of Siena, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Gimignano may take around 43 min. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Take your self-guided tour to Porta San Giovanni, a frequently visited monument that everyone visiting San Gimignano should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Next, head to Piazza Del Duomo. This history-steeped public square is one of the most intriguing attractions in the region. Don’t miss out on Palazzo Comunale, Pinacoteca, Torre Grossa, a historic museum, popular among locals as well as travelers. Parco Della Rocca is an excellent attraction to visit next. Spend some time learning more about this locally appreciated park before you continue your journey.

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

Parco Archeologico "enrico Fiumi" is an up-and-coming archeological site we recommend making time to visit today. Discover its gorgeous features before continuing your self-guided tour.

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

Get a good night's sleep and look forward to another great day on the road 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 Montepulciano promises more breathtaking discoveries and enriching experiences!

Set your GPS to Montepulciano and hit the road. Expect a journey of approximately 50 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Montepulciano beckons with new experiences!

Head to Az. Agr. Crociani Susanna Crociani, a curiosity-inducing winery in Montepulciano. Explore its visually striking features at your own pace before you continue your journey to your next sight, Fortezza Medicea. This underrated castle is a top recommendation in the area.

When you’ve had your share of Montepulciano, 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 20 min.

Your self-guided tour starts at Palazzo Piccolomini, Pienza, a locally appreciated palace that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Pienza. Pienza offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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.

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

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