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 Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Florence on today’s itinerary. First up is the world-famous historical landmark, Ponte Vecchio. Afterward, continue to Uffizi Gallery, an art gallery every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Basilica Of Santa Croce In Florence. This well-known church is an essential stop. Following that, head to Piazza Della Signoria, another must-visit site that will enhance your experience. Don’t forget to stop by Central Market, a popular food market in the city.

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.

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 and reflect on the day'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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences in Italy!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Pisa, Lucca, and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in San Gimignano, where you’ll be staying for 1 night.

Get ready to discover some of the most iconic wonders in Florence, including a church, a public square, a monument, a historical landmark and much more! Start your day at Pisa Cathedral. This UNESCO world heritage-designated church is an underrated place to see in Florence. Then, wander over to Piazza Del Duomo, Pisa. If culturally significant sites excite you, this public square will be right up your alley. Nearby, you’ll also find Leaning Tower Of Pisa. This culturally significant monument is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Mura Di Lucca is a worthwhile spot in the city that will captivate you with its unique charm. When you’re done at the historical landmark, don’t forget to check out the romantic Piazza Del Duomo. Take a moment to appreciate the fascinating details of this locally appreciated public square.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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 explore more of San Gimignano, 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.

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and San Regolo, 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 Greve in Chianti. You’ll stay here for 1 night.

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This breathtaking monument is sure to impress. Next on your list is Palazzo Salimbeni, another must-visit landmark and often recommended palace renowned for its symbolic features.

While exploring and sightseeing, take time to savor the culture of San Gimignano by sampling some local delicacies. When you’re ready for more sightseeing, head to Siena Cathedral. This history-steeped church is an essential place to visit for anyone looking for the full San Gimignano experience. We also recommend visiting Piazza Del Campo, an extraordinary public square. Nearby, you'll also find Porta Pispini, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Castello Di Brolio and wrap up your day with its enchanting appeal.

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

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

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

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Il Mulino. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

A blend of family-friendly attractions, breathtaking views, and photo-friendly spots await you in Greve in Chianti on today’s itinerary. First up is the locally renowned church, Basilica Of San Francesco D'assisi. Afterward, continue to Eremo Delle Carceri, a monastery every traveler should visit.

As you explore Greve in Chianti’s charming streets, take in the lively atmosphere and get to know the character of the town. Next, make your way to Rocca Maggiore. This often recommended castle is an essential stop. Following that, head to Melone Secondo Del Sodo, another must-visit site that will enhance your experience.

At the end of the day, you will drive to Florence, 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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