5-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling west to Siena and San Gimignano

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Florence and Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the iconic Ponte Vecchio, a grand historical landmark in Florence. Next, go to Uffizi Gallery.

After visiting Ponte Vecchio and Uffizi Gallery, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of Santa Croce In Florence. This culturally significant church offers a unique experience. Siena Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Pubblico Palace, one of the most culturally significant places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Piazza Del Campo.

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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 Greve in Chianti and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.

Savor the day by visiting some of the best places to see in Siena, including a castle, a monument, a museum, a public square, a church and much more! Start your adventure at Castle Of Verrazzano. This increasingly popular castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta San Giovanni located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Sangimignano1300. Its respected features will captivate you. After the museum, continue your tour of the town with a visit to Palazzo Comunale, Pinacoteca, Torre Grossa. Visitors usually appreciate the picture-perfect features of this museum. Next up is Piazza Del Duomo, a highly recommended public square. For a change of pace, head to Chiesa Di Sant'agostino. As one of the most frequently visited attractions in Siena, this church is the perfect place to end your self-guided sightseeing tour.

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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Say good night to San Gimignano and look forward to another great day of your road trip 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 - Pisa and Vernazza. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Enjoy the perfect balance of relaxation and exploration in San Gimignano today. One of the most iconic attractions included on the itinerary is Leaning Tower Of Pisa. This UNESCO world heritage-designated monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo, Pisa and learn what makes this breathtaking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the frequently visited Pisa Cathedral. After exploring the church, head to Ruins Of Doria Tower. This up-and-coming monument is a highlight in San Gimignano.

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.

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.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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