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

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.

One of the most iconic places you can visit today in Florence is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Savor the day by visiting some of the best places to see in Florence, including a historical landmark, an art gallery, a church, a public square, a food market and much more! Start your adventure at Ponte Vecchio. This iconic historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Uffizi Gallery located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Basilica Of Santa Croce In Florence. Its inviting features will captivate you. After the church, continue your tour of the city with a visit to Piazza Della Signoria. Visitors usually appreciate the symbolic features of this public square. Next up is Central Market, a highly recommended food market.

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.

Visit Mercato Centrale in Florence for an unforgettable shopping experience. Browse unique and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Mercato Centrale has to offer, including attractions, essential services, and vibrant community activities.

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

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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

Today’s agenda in Florence includes a church, a public square, a monument, a historical landmark and much more! Pisa Cathedral is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Del Duomo, Pisa, a wondrous public square, located just a leisurely stroll away. Next, head to Leaning Tower Of Pisa, a noteworthy monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the locally appreciated Mura Di Lucca. If you’re looking for more, Piazza Del Duomo is also a worthwhile attraction that is worthwhile a visit.

At the end of the day, you will drive to San Gimignano, 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 San Gimignano's most popular restaurants, and connect with friendly locals for an authentic adventure.

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, Siena and San Regolo. When you’re not sightseeing, take time to relax at your selected hotel in Greve in Chianti, where you’ll be staying for 1 night.

Today’s itinerary in San Gimignano covers several incredible sights, including a monument, a palace, a church, a public square, a historical landmark, a castle and much more! Start your adventure at Fortezza Medicea (siena). This frequently visited monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the photogenic wonders of Palazzo Salimbeni, a must-see palace in the city.

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 Siena Cathedral. This interesting church offers an enriching experience. For a change of pace, head to Piazza Del Campo, where you can take in history-steeped features. Conclude your self-guided sightseeing tour with a visit to Porta Pispini and Castello Di Brolio. 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 Greve in Chianti. Check in and spend some time relaxing before you head out to tour the town.

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

Savor another day of unforgettable experiences in Italy!

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 Santa Maria degli Angeli and Il Mulino. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Today's adventure in Greve in Chianti promises more breathtaking discoveries and enriching experiences! Begin at Basilica Of San Francesco D'assisi. This picture-perfect church is a highlight of any visit in the town. Then, enjoy Eremo Delle Carceri, another history-steeped attraction that never fails to captivate visitors. Next, head over to Rocca Maggiore, one of the town’s most worthwhile attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Melone Secondo Del Sodo. This picture-perfect archeological site is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

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

Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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.