7-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena

On day 2 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 2 nights.

Catch Galleria Dell'accademia before the crowds roll in. This photogenic art gallery is sure to ignite your curiosity. Next, dive into the history-steeped features of Piazza Della Signoria, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Ponte Vecchio, a timeless historical landmark. For a change of scene, check out Uffizi Gallery, known for its eye-catching features. We also recommend visiting Basilica Of Santa Croce In Florence. This church is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazzale Michelangelo, yet another astonishing attraction in Florence.

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.

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.

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.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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 3 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 16 min. Pisa welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Piazza Del Duomo, Pisa. Spend some time admiring the historic features of the public square before you continue to your next stop. Then, head to Leaning Tower Of Pisa. This globally renowned monument is a traveler-favorite in the city.

Continue your road trip and head to your next destination, Lucca. This car ride takes around 32 min.

Savor the day by heading to Guinigi Tower, an intriguing monument that draws visitors from near and far. When you're done, continue to San Michele In Foro, where you can soak in the picture-perfect surroundings.

Next, explore Mura Di Lucca, yet another intriguing place to see in the area.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

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.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Siena and San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 2 nights.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 12 min.

Savor the day by heading to Siena Cathedral, a locally renowned church that draws visitors from near and far. When you're done, continue to Piazza Del Campo, where you can soak in the awe-inspiring surroundings.

Next, explore Pubblico Palace, yet another frequently visited place to see in the area.

Admire the views and listen to some good music as you drive in the direction of San Gimignano.

Our first attraction recommendation in San Gimignano is Parco Della Rocca, an up-and-coming park that draws attention for its history-steeped features. Spend some time soaking in the atmosphere before continuing to Sangimignano1300, a heritage-rich museum 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 Piazza Del Duomo, an increasingly popular public square that offers a unique experience.

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.

Siena 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 Siena.

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. Known for great service, it’s a fantastic choice for tonight in Siena.

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 look forward to more memorable moments to come!

On day 5 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Siena, there’s no need to rush. Experience San Regolo and Castellina in Chianti to the fullest today with this curated day itinerary.

San Regolo is brimming with adventures.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: San Regolo. Expect your car journey to take a minimum of 36 min. When you arrive in San Regolo, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castello Di Brolio, a curiosity-inducing castle that everyone visiting San Regolo should see.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Castellina in Chianti may take around 40 min. Upon your arrival in Castellina in Chianti, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready for some sights, head to Tumulo Di Montecalvario, a frequently visited archeological site in Castellina in Chianti. Explore its heritage-rich features at your own pace before you continue your journey to your next attraction, Rocca Di Castellina In Chianti. This underrated castle is a top recommendation in the area.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

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

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Unwind after your meal by stepping into Charlie Mixology Bar Di Aldinucci Riccardo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Pinacoteca offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook San Paolo Pub, another top-rated bar in the area.

Savor another day of unforgettable experiences 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. Santa Maria degli Angeli and Perugia are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Fasten your seatbelt and make your way to your next stop — Santa Maria degli Angeli, home to many well-known sights in the region. Keep in mind that your travel time from Siena to Santa Maria degli Angeli may take around 1 hour 36 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

Spend your afternoon discovering Basilica Of San Francesco D'assisi, a popular church known for its picture-perfect features. Next, continue your sightseeing at Rocca Maggiore, a beloved castle.

Fasten your seatbelt and make your way to your next stop — Perugia, home to many well-known sights in the region. Keep in mind that your travel time from Santa Maria degli Angeli to Perugia may take around 34 min without traffic disruptions. Upon arrival in Perugia, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is The Fontana Maggiore. Spend some time admiring the historic features of the monument before you continue to your next stop. Then, head to Piazza Iv Novembre. This curiosity-inducing public square is a traveler-favorite in the town.

If you're keen to see more, continue to Perugia Cathedral. Feed your curiosity by learning something new about the church.

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

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.

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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