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 one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Today, you'll explore some of the most beautiful places in Florence, including a historical landmark, an art gallery, a church, a public square, a food market and much more! Start your day with a visit to Ponte Vecchio. This wondrous historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Uffizi Gallery, 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 Basilica Of Santa Croce In Florence, a locally renowned church in the city. If you’re up for more discoveries, don’t forget to reserve some time for 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.

Bring home unique finds from Florence's bustling shopping hub, Via de' Tornabuoni. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via de' Tornabuoni offers plenty of options, including primary services, unique landmarks, and community events.

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.

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.

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.

Raise your glass to another unforgettable day in Italy!

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

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most curiosity-inducing attractions included on the itinerary is Pisa Cathedral. This stunning church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo, Pisa and learn what makes this stunning public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Leaning Tower Of Pisa. After exploring the monument, head to Mura Di Lucca. This often recommended historical landmark is a highlight in Florence. As your day continues, stop by Piazza Del Duomo, known for its visually striking features.

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

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

Raise your glass to another unforgettable 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.

Get ready for an exciting day in San Gimignano. Today’s sightseeing agenda includes a monument, a palace, a church, a public square, a historical landmark, a castle and much more! Begin your adventure at Fortezza Medicea (siena). This is a curiosity-inducing monument you should not miss. Another must-see is Palazzo Salimbeni, an often recommended palace in San Gimignano.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Piazza Del Campo, another of the city’s extraordinary attractions. We recommend continuing your self-guided tour at Porta Pispini, a historic place of interest in the city. If time allows, add Castello Di Brolio to your itinerary. This increasingly popular castle offers the perfect finishing touch to your day in San Gimignano.

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.

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

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.

Today’s itinerary in Greve in Chianti covers several incredible sights, including a church, a monastery, a castle, an archeological site and much more! Start your adventure at Basilica Of San Francesco D'assisi. This locally renowned church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Eremo Delle Carceri, a must-see monastery in the town.

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 Rocca Maggiore. This locally appreciated castle offers an enriching experience. For a change of pace, head to Melone Secondo Del Sodo, where you can take in breathtaking features. 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 Florence. Check in and spend some time relaxing before you head out to tour the city.

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.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.

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