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.

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Ponte Vecchio is the first of them. Spend some time admiring this enchanting historical landmark before continuing your journey. Uffizi Gallery is your next stop. This astonishing art gallery is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Basilica Of Santa Croce In Florence. This photogenic church is a sight to behold. To round off your sightseeing experience, visit Piazza Della Signoria and Central 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.

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

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

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, a public square, a monument, a historical landmark and much more! Begin your adventure at Pisa Cathedral. This is an intriguing church you should not miss. Another must-see is Piazza Del Duomo, Pisa, a globally renowned public square in Florence.

When you’re ready for the next sight, head to Leaning Tower Of Pisa. From there, take a leisurely stroll to Mura Di Lucca, another of the city’s locally appreciated attractions. We recommend continuing your self-guided tour at Piazza Del Duomo, an inviting place of interest in the city.

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

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

Raise your glass to another unforgettable day in Italy!

On day 4 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 Siena and San Regolo. In the evening, you’ll end up in Greve in Chianti, where you will stay for 1 night.

A blend of family-friendly attractions, breathtaking views, and picturesque spots await you in San Gimignano on today’s itinerary. First up is the beloved monument, Fortezza Medicea (siena). Afterward, continue to Palazzo Salimbeni, a palace every traveler should visit.

As you explore San Gimignano’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Siena Cathedral. This captivating church is an essential stop. Following that, head to Piazza Del Campo, another must-visit site that will enhance your experience. Don’t forget to stop by Porta Pispini, an often recommended historical landmark in the city. Finally, end your day with a visit to Castello Di Brolio, a respected castle that offers the perfect conclusion to your sightseeing of the day.

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.

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

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

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Il Mulino, 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 Florence. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Greve in Chianti. Some of the town’s most loved attractions await! Basilica Of San Francesco D'assisi is the perfect place to start. This church is one of the most well-known places to visit in Greve in Chianti. Next, head to Eremo Delle Carceri, a worthwhile monastery, known for its inviting features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Rocca Maggiore. This respected castle is a highly recommended experience. Nearby, you'll also find Melone Secondo Del Sodo. Visit these for an interesting touch to your journey.

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 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.

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.

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.