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

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 1 night.

Oltrarno is a fantastic place you can explore today in Florence. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Florence-way-of-life and visit all the nearby sights.

Ponte Vecchio is perfect for a self-paced visit during the day. This history-steeped historical landmark is sure to impress. Next on your list is Uffizi Gallery, another must-visit landmark and impressive art gallery renowned for its picture-perfect features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Basilica Of Santa Croce In Florence. This culturally significant church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Piazza Della Signoria, a spectacular public square. Nearby, you'll also find Central Market, ready to add charm to your journey.

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.

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

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

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

Check out the often recommended church, Pisa Cathedral. Afterward, continue to Piazza Del Duomo, Pisa, a public square 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 Leaning Tower Of Pisa. This world-famous monument is an essential stop. Following that, head to Mura Di Lucca, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Duomo, an increasingly popular public square in the city.

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.

San Gimignano 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 San Gimignano.

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

Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of Siena and San Regolo. At the end of the day, enjoy the comforts of a top-rated hotel in Greve in Chianti, where you'll spend 1 night.

Fortezza Medicea (siena) is an ideal stop early in the day. This locally appreciated monument is a must-visit in the city. When you’re ready for your next discovery, continue to Palazzo Salimbeni, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring San Gimignano on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Siena Cathedral, a notable church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Del Campo and Porta Pispini. End your day with a visit to Castello Di Brolio, an increasingly popular castle that’s sure to leave a lasting impression.

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

Raise your glass to another unforgettable day in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Santa Maria degli Angeli and Il Mulino. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Enjoy all that Basilica Of San Francesco D'assisi has to offer. This is a captivating church you should not miss. Another must-see is Eremo Delle Carceri, an often recommended monastery in Greve in Chianti.

When you’re ready for the next sight, head to Rocca Maggiore. From there, take a leisurely stroll to Melone Secondo Del Sodo, another of the town’s locally appreciated attractions.

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 dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Ristorante Buca Mario, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Agricola Toscana, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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