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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Ponte Vecchio. This romantic historical landmark is a highlight of any visit in the city. Then, enjoy Uffizi Gallery, another romantic attraction that never fails to captivate visitors. Next, head over to Basilica Of Santa Croce In Florence, one of the city’s most well-known attractions, known for its photogenic features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Della Signoria. This detailed public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Central Market, a notable food market, and take a stroll around the area.

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.

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 lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

Savor another day of unforgettable experiences 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.

Today, you'll explore some of the most beautiful places in Florence, including a church, a public square, a monument, a historical landmark and much more! Start your day with a visit to Pisa Cathedral. This locally appreciated church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Duomo, Pisa, which may be one of the most picture-perfect places you will experience today.

One of the best things about exploring Florence 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 Leaning Tower Of Pisa, a timeless monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Mura Di Lucca and Piazza Del Duomo.

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.

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.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and San Regolo. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Greve in Chianti. You will spend 1 night here for some well-deserved relaxation.

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This instagrammable monument is sure to impress. Next on your list is Palazzo Salimbeni, another must-visit landmark and intriguing palace renowned for its eye-catching 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 romantic 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 romantic 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.

Celebrate another amazing day of your road trip adventure in Italy!

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.

Set out on a day brimming with fun adventures, scenic views, and picturesque spots. Start at the popular Basilica Of San Francesco D'assisi, a picture-perfect church in Greve in Chianti. Next, go to Eremo Delle Carceri.

After visiting Basilica Of San Francesco D'assisi and Eremo Delle Carceri, have a stroll along Greve in Chianti's streets and take in the local charm. Continue your sightseeing by heading to Rocca Maggiore. This history-steeped castle offers a unique experience. Melone Secondo Del Sodo is another noteworthy attraction worthwhile a visit.

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.

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.

Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!