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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Florence and Siena, 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 Siena. You’ll stay here for 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a historical landmark, an art gallery, a church, a palace, a public square and much more! Begin your adventure at Ponte Vecchio. This is a timeless historical landmark you should not miss. Another must-see is Uffizi Gallery, a famous art gallery in Florence.

When you’re ready for the next sight, head to Basilica Of Santa Croce In Florence. From there, take a leisurely stroll to Siena Cathedral, another of the city’s interesting attractions. We recommend continuing your self-guided tour at Pubblico Palace, a historic place of interest in the city. If time allows, add Piazza Del Campo to your itinerary. This widely recognized public square offers the perfect finishing touch to your day in Florence.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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

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.

Today’s agenda in Siena includes a castle, a monument, a museum, a public square, a church and much more! Castle Of Verrazzano is must-visit castle and a great starting point for the day. Next, continue your journey to Porta San Giovanni, a curiosity-inducing monument, located just a leisurely stroll away. Next, head to Sangimignano1300, a visually striking museum, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the curiosity-inducing Palazzo Comunale, Pinacoteca, Torre Grossa. If you’re looking for more, Piazza Del Duomo is also a worthwhile attraction that is worthwhile a visit. Lastly, don’t miss Chiesa Di Sant'agostino, a place of inviting interest in the town.

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.

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

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 - 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.

Get ready to discover some of the most iconic wonders in San Gimignano, including a monument, a public square, and a church. Start your day at Leaning Tower Of Pisa. This culturally significant monument is a wondrous place to see in San Gimignano. Then, wander over to Piazza Del Duomo, Pisa. If UNESCO world heritage-listed sites excite you, this public square will be right up your alley. Nearby, you’ll also find Pisa Cathedral. This UNESCO world heritage-listed church is a favorite among visitors.

San Gimignano offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Ruins Of Doria Tower is a frequently visited spot in the city that will captivate you with its unique charm.

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.

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.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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