6-Day Italy Self-Drive Road Trip With Itinerary from Florence to San Gimignano and Greve in Chianti

Day 2 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

A top thing to do today is to explore Oltrarno, a must-see neighborhood in Florence. It's the perfect starting point for touring the top attractions in the area.

No visit to Florence is complete without Ponte Vecchio. This globally renowned historical landmark is one of the top attractions in the city. Proceed to Uffizi Gallery, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Basilica Of Santa Croce In Florence. This notable church is a traveler-favorite. Not far away, you’ll find Piazza Della Signoria, another key site on your sightseeing itinerary. Central Market is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences in Italy!

Your itinerary for day 3 of your road trip in Italy includes 3 stops and features some of the highlights of Pisa, Lucca, and San Gimignano. At the end of the day, enjoy the comforts of a top-rated hotel in San Gimignano, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Pisa. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 15 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

For a more meaningful self-guided tour of the city's best attractions, visit Pisa Cathedral, an increasingly popular church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Piazza Del Duomo, Pisa and admire its UNESCO world heritage-listed features.

When you’re ready, continue to Leaning Tower Of Pisa, a world-famous monument beloved by locals and tourists alike.

When you’re ready to jump back into the car and say goodbye to Pisa, you’ll hit the road in the direction of Lucca. This drive usually takes around 31 min.

One of our top recommendations for your sightseeing is Mura Di Lucca. Spend some time admiring the majestic features of the historical landmark before you continue to your next stop.

Set your GPS to San Gimignano and hit the road. Expect a journey of approximately 1 hour 34 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Piazza Del Duomo is an up-and-coming public square we recommend visiting today. Discover its UNESCO world heritage-designated features before continuing your self-guided tour.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in San Gimignano. San Gimignano 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 San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine.

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

On day 4 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Regolo are on today's agenda. In the evening, you’ll end up in Greve in Chianti, where you will stay for 1 night.

After soaking in San Gimignano’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 46 min. When you arrive in Siena, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Fortezza Medicea (siena). Spend some time admiring the picture-perfect features of the monument before you continue to your next stop. Then, head to Palazzo Salimbeni. This worthwhile palace is a traveler-favorite in the city.

If you're keen to see more, continue to Siena Cathedral. Feed your curiosity by learning something new about the church. Next, take your journey to Piazza Del Campo, a famous public square. Conclude your sightseeing at Porta Pispini, known for its breathtaking features.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Regolo. This drive usually takes around 32 min, without any stops or traffic disruptions.

Set out on a self-guided sightseeing tour at Castello Di Brolio and explore the visually striking features.

At the end of the day, you will drive to Greve in Chianti, 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 Greve in Chianti's most popular restaurants, and connect with friendly locals for a true cultural experience.

Raise your glass to another unforgettable day in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Santa Maria degli Angeli and Il Mulino. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

When you’re ready to jump back into the car and say goodbye to Greve in Chianti, you’ll hit the road in the direction of Santa Maria degli Angeli. This drive usually takes around 2 hours 10 min.

Savor the day by heading to Basilica Of San Francesco D'assisi, a popular church that draws visitors from near and far. When you're done, continue to Eremo Delle Carceri, where you can soak in the inviting surroundings.

Next, explore Rocca Maggiore, yet another frequently visited place to see in the area.

Continue your road trip and head to your next destination, Il Mulino. This car ride takes around 1 hour 3 min.

Savor the day by heading to Melone Secondo Del Sodo, an underrated archeological site that draws visitors from near and far.

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

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

Explore the vibrant nightlife at Gosh* after your meal, a hub for lively evenings and memorable moments. Or, head to Antico Caffè Del Moro - Art Bar Firenze for a great selection of flavorful drinks and a charming setting. Furthermore, Quelo Bar is perfect for those looking to extend their night with a touch of local flavor.

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