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.

Oltrarno is a neighborhood that stands out as one of the must-see places in Florence. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Florence. Your adventure starts at Ponte Vecchio, a globally renowned local hot spot. Another notable attraction to explore is Uffizi Gallery. This famous art gallery is known for its awe-inspiring appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Of Santa Croce In Florence. This respected church offers a fascinating experience that many visitors find memorable. Piazza Della Signoria is also worth visiting, along with Central Market. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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 San Lorenzo Market 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 San Lorenzo Market has to offer, including attractions, essential services, and vibrant community activities.

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

Don’t miss out on dining 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.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!

On day 3 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 Pisa, Lucca, and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.

Get ready for a day filled with fun adventures, breathtaking views, and photo-friendly spots in the charming city of Florence. Your adventure starts at Pisa Cathedral, a locally appreciated local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This world-famous public square is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This picture-perfect monument offers a fascinating experience that many visitors find memorable. Mura Di Lucca is also worth visiting, along with Piazza Del Duomo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

Celebrate another amazing day of your road trip adventure 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.

Set out on a day brimming with fun adventures, breathtaking views, and picturesque spots. Start at the often recommended Fortezza Medicea (siena), a historic monument in San Gimignano. Next, go to Palazzo Salimbeni.

After visiting Fortezza Medicea (siena) and Palazzo Salimbeni, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Siena Cathedral. This enchanting church offers a unique experience. Piazza Del Campo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Porta Pispini, one of the most culturally significant places to visit in San Gimignano. If you still have some time left for sightseeing, we also recommend stopping by Castello Di Brolio.

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.

As you explore more of Greve in Chianti, 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.

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

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.

Immerse yourself in Greve in Chianti’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Of San Francesco D'assisi. This culturally significant church is sure to ignite your curiosity. Next, dive into the picturesque features of Eremo Delle Carceri, a must-visit monastery in the town.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Rocca Maggiore, an increasingly popular castle. For a change of scene, check out Melone Secondo Del Sodo, known for its culturally significant features.

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.

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

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.

Extend your evening after a delightful meal by visiting Gosh*, which offers the perfect atmosphere for a night out. Moreover, Antico Caffè Del Moro - Art Bar Firenze is another popular option for a drink or two. Likewise, Quelo Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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