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 across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Start by visiting Basilica Of Santa Croce In Florence, a prime spot to begin your journey. This culturally significant church is sure to impress. Next on your list is Galleria Dell'accademia, another must-visit landmark and captivating art gallery renowned for its standout 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 UNESCO world heritage-designated 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 popular 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.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Savor another day of unforgettable experiences in Italy!

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Pisa and Lucca, 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 Lucca. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Pisa Cathedral is the perfect place to start. This church is one of the most worthwhile places to visit in Florence. Next, head to Piazza Del Duomo, Pisa, an iconic public square, known for its culturally significant 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 Leaning Tower Of Pisa. This culturally significant monument is a highly recommended experience. Nearby, you'll also find Guinigi Tower and Piazza Dell'anfiteatro. Visit these for an interesting touch to your journey.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Lucca. Lucca offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Lucca's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a delicious dinner at Gli Orti di Via Elisa, an excellent option for tonight's dining. Looking for something different? Bar Caffè Ristretto offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Schiaffino. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Lucca.

Continue the enjoyment post-dinner at Lebowski - Cocktail Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Blend offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Franklin'33. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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.

Today’s itinerary in Lucca covers several incredible sights, including a national park and a church. Start your adventure at Cinque Terre National Park. This notable national park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Convent Of The Capuchin Friars, a must-see church in the village.

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 Parrocchia Di S. Giovanni Battista. This up-and-coming church offers an enriching experience. These sights offer a fulfilling end to a perfect day.

At the end of the day, you will drive to Monterosso al Mare, 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 Monterosso al Mare. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Pizzeria La Smorfia, a highly-rated dining destination in Monterosso al Mare. If you're eager to try something different, consider La Taverna di Monterosso, another top spot with a tantalizing menu. You might also want to secure a reservation at Hotel Albergo Degli Amici. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Monterosso al Mare this evening.

Keep the evening going at Enoteca Da Eliseo, a great choice for enjoying the after-dinner hours with a drink.

Relax and recharge in preparation for another adventurous day 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Monterosso al Mare allows for both. Start by heading to Fortezza Medicea (siena). This locally appreciated monument provides an insightful glimpse into the city's identity. Next, discover Siena Cathedral, an inviting church, promising a delightful encounter.

Continue your sightseeing with a visit to Facciatone, an underrated observation deck. When you’re done, don’t forget to make a stop at the spectacular Piazza Del Campo. Round off your day at Tower Of Mangia, another gem in Monterosso al Mare with historic features to discover.

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

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 and reflect on the day's adventures.

Make sure to reserve a table at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists. Or, head to Maudit Pub. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Impero Siena, another top-rated place in the area.

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

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 San Gimignano and Volterra. In the evening, you’ll end up in Volterra, where you will stay for 1 night.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Porta San Giovanni. This underrated monument is a culturally significant place to see in Siena. Continue your discovery at Piazza Del Duomo, a visually striking public square with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Palazzo Comunale, Pinacoteca, Torre Grossa. This increasingly popular museum offers a culturally significant encounter with Siena. Next, make your way to Parco Della Rocca to add another highlight to your day. After that, visit Parco Archeologico "enrico Fiumi", an up-and-coming archeological site that’s sure to impress. 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.

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

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

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Montepulciano and Pienza, 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 Pienza. You’ll stay here for 1 night.

Get ready for an exciting day in Cortona. Today’s sightseeing agenda includes a winery, a castle, and a palace. Begin your adventure at Az. Agr. Crociani Susanna Crociani. This is a frequently visited winery you should not miss. Another must-see is Fortezza Medicea, a locally appreciated castle in Cortona.

When you’re ready for the next sight, head to Palazzo Piccolomini, Pienza.

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

As you explore more of Pienza, 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.

Savor another day of unforgettable experiences in Italy!