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.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church and an art gallery. Begin your adventure at Basilica Of Santa Croce In Florence. This is a captivating church you should not miss. Another must-see is Galleria Dell'accademia, a popular art gallery in Florence.

When you’re ready for the next sight, head to Cathedral Of Santa Maria Del Fiore. From there, take a leisurely stroll to Basilica Di Santa Maria Novella, Firenze (fi), another of the city’s well-known attractions.

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.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Lucca. At the end of the day, you will enjoy the comforts of a top-rated hotel in Lucca, which will be your home away from home for 1 night.

Today, you'll explore some of the most beautiful places in Florence, including a church, a public square, and a monument. Start your day with a visit to Pisa Cathedral. This curiosity-inducing church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Duomo, Pisa, which may be one of the most historic places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Leaning Tower Of Pisa, a globally renowned monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Guinigi Tower and Piazza Dell'anfiteatro.

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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Lucca. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

After enjoying a fulfilling meal, continue your evening at Lebowski - Cocktail Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Blend offers a welcoming atmosphere for easing into the nightlife. Similarly, Franklin'33 provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Corniglia and Monterosso al Mare. When you’re not sightseeing, take time to relax at your selected hotel in Monterosso al Mare, where you’ll be staying 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 well-known national park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking 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 locally appreciated church offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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.

Extend your evening after a delightful meal by visiting Enoteca Da Eliseo, which offers the perfect atmosphere for a night out.

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

On day 5 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 Siena. In the evening, you’ll end up in Siena, where you will stay for 1 night.

A blend of family-friendly attractions, breathtaking views, and picturesque spots await you in Monterosso al Mare on today’s itinerary. First up is the increasingly popular monument, Fortezza Medicea (siena). Afterward, continue to Siena Cathedral, a church every traveler should visit.

As you explore Monterosso al Mare’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Facciatone. This curiosity-inducing observation deck is an essential stop. Following that, head to Piazza Del Campo, another must-visit site that will enhance your experience. Don’t forget to stop by Tower Of Mangia, a beloved monument in the city.

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.

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.

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

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip 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.

Get ready to discover some of the most iconic wonders in Siena, including a monument, a public square, a museum, a park, an archeological site and much more! Start your day at Porta San Giovanni. This breathtaking monument is an intriguing place to see in Siena. Then, wander over to Piazza Del Duomo. If enchanting sites excite you, this public square will be right up your alley. Nearby, you’ll also find Palazzo Comunale, Pinacoteca, Torre Grossa. This breathtaking museum is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Parco Della Rocca is a locally appreciated spot in the village that will captivate you with its unique charm. When you’re done at the park, don’t forget to check out the instagrammable Parco Archeologico "enrico Fiumi". Take a moment to appreciate the fascinating details of this worthwhile archeological site.

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.

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

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

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Montepulciano and Pienza. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pienza, which will be your home away from home for 1 night.

Brace yourself for today’s incredible lineup of attractions in Cortona, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Az. Agr. Crociani Susanna Crociani, an underrated winery in the town. Then, head to Fortezza Medicea and soak in the ambiance of this visually striking castle.

There are many interesting places to see in Cortona, and when you are ready for more, go to Palazzo Piccolomini, Pienza. This is one of the town’s most locally appreciated romantic spots of interest.

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

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