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

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Florence and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Ponte Vecchio. This history-steeped historical landmark is sure to ignite your curiosity. Next, dive into the instagrammable features of Uffizi Gallery, a must-visit art gallery in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Basilica Of Santa Croce In Florence, a well-known church. For a change of scene, check out Siena Cathedral, known for its majestic features.

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

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Greve in Chianti 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’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, an up-and-coming monument, located just a leisurely stroll away. Next, head to Sangimignano1300, an UNESCO world heritage-listed 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. If you’re looking for more, Palazzo Comunale, Pinacoteca, Torre Grossa is also a beloved attraction that is worthwhile a visit. Lastly, don’t miss Piazza Del Duomo, an intriguing gem to see in the town.

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.

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

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

On day 4 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 and Vernazza. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the world-famous Leaning Tower Of Pisa, a breathtaking monument in San Gimignano. Next, go to Piazza Del Duomo, Pisa.

After visiting Leaning Tower Of Pisa and Piazza Del Duomo, Pisa, take time to explore San Gimignano's streets and absorb its charm. Continue your sightseeing by heading to Pisa Cathedral. This symbolic church offers a unique experience. Ruins Of Doria Tower is another noteworthy stop.

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.

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.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!