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

Make a stop at Basilica Of Santa Croce In Florence. This popular church is a must-visit for travelers looking for a unique holiday experience. Make your way to Galleria Dell'accademia located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Cathedral Of Santa Maria Del Fiore. Its inviting features will captivate you. After the church, continue your tour of the city with a visit to Basilica Di Santa Maria Novella, Firenze (fi). Visitors usually appreciate the enchanting features of this church.

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.

Bring home unique finds from Florence's bustling shopping hub, Via de' Tornabuoni. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via de' Tornabuoni offers plenty of options, including primary services, unique landmarks, and community events.

Florence 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 Florence.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Pisa and Lucca. At the end of the day, you will retreat to the hotel of your choice in Lucca, where will spend 1 night.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 15 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Spend your afternoon discovering Pisa Cathedral, an often recommended church known for its historic features. Next, continue your sightseeing at Piazza Del Duomo, Pisa, an iconic public square.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Leaning Tower Of Pisa and uncover the details of this picture-perfect monument.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Lucca. Expect your car journey to take a minimum of 32 min. When you arrive in Lucca, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Guinigi Tower. Spend some time admiring the visually striking features of the monument before you continue to your next stop. Then, head to Piazza Dell'anfiteatro. This well-known public square is a traveler-favorite 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 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.

Make sure to reserve a table at Gli Orti di Via Elisa, an iconic dining spot in Lucca. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bar Caffè Ristretto, a popular restaurant in Lucca. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Schiaffino, a hidden gem nestled in Lucca. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Corniglia and Monterosso al Mare. When you’re not sightseeing, take time to relax at your chosen hotel in Monterosso al Mare, where you’ll be staying for 1 night.

Fasten your seatbelt and make your way to your next stop — Corniglia, home to many well-known sights in the region. Keep in mind that your travel time from Lucca to Corniglia may take around 1 hour 31 min without traffic disruptions. Upon arrival in Corniglia, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Cinque Terre National Park, a well-known national park in Corniglia. Explore its romantic features at your own pace before you continue your journey.

When you’ve had your share of Corniglia, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Monterosso al Mare. Your travel time is around 28 min.

Our first attraction recommendation in Monterosso al Mare is Convent Of The Capuchin Friars, a frequently visited church that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to Parrocchia Di S. Giovanni Battista, a heritage-rich church that stands out in the village.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Monterosso al Mare. Monterosso al Mare 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 Monterosso al Mare, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Pizzeria La Smorfia, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna di Monterosso? It's another excellent option with a diverse menu. Consider reserving a table at Hotel Albergo Degli Amici as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Monterosso al Mare.

Continue your evening by exploring the vibrant nightlife scene at Enoteca Da Eliseo, a prime destination for a thrilling night out.

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

Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 1 night.

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.

Our first attraction recommendation in Siena is Fortezza Medicea (siena), a worthwhile monument that draws attention for its culturally significant features. Spend some time soaking in the atmosphere before continuing to Siena Cathedral, a symbolic church that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Facciatone, a worthwhile observation deck that offers a unique experience. Be sure to also explore Piazza Del Campo, a nearby public square, highly recommended by other travelers. End your self-guided tour at Tower Of Mangia, a historic monument and the perfect final attraction in Siena.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax 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.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 6 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. San Gimignano and Volterra are on today's agenda. In the evening, you’ll end up in Volterra, where you will stay for 1 night.

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.

Savor the day by heading to Porta San Giovanni, an often recommended monument that draws visitors from near and far. When you're done, continue to Piazza Del Duomo, where you can soak in the romantic surroundings.

Next, explore Palazzo Comunale, Pinacoteca, Torre Grossa, yet another locally appreciated place to see in the area. After the museum, make time to go to Parco Della Rocca. This enchanting park is well worth the visit.

Volterra’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of San Gimignano behind. This drive usually takes around 38 min. Volterra welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Parco Archeologico "enrico Fiumi" and explore the awe-inspiring features.

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.

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

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Montepulciano and Pienza. At the end of the day, you will retreat to the hotel of your choice in Pienza, where will spend 1 night.

Continue your road trip and head to your next destination, Montepulciano. This car ride takes around 50 min.

One of our top recommendations for your sightseeing is Az. Agr. Crociani Susanna Crociani. Spend some time admiring the gorgeous features of the winery before you continue to your next stop. Then, head to Fortezza Medicea. This increasingly popular castle is a traveler-favorite in the town.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pienza may take around 20 min. Upon your arrival in Pienza, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Palazzo Piccolomini, Pienza, an increasingly popular palace known for its history-steeped features.

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

Pienza 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 Pienza.

Head back to your accommodation in Pienza and get some rest to prepare for another magical day of your road trip in Italy.