5-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence and Siena

On day 2 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly spots. Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Leaning Tower Of Pisa is the first of them. Spend some time admiring this picture-perfect monument before continuing your journey. Piazza Del Duomo, Pisa is your next stop. This world-famous public square is one of the best-rated sights in Pisa.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Basilica Of Santa Croce In Florence. This heritage-rich church is a sight to behold. To round off your sightseeing experience, visit Uffizi Gallery and Ponte Vecchio. If time allows, end your day with Piazza Della Signoria, a romantic public square that offers a memorable conclusion to your exploration.

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 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.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

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 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.

Start your day with a visit to Cathedral Of Santa Maria Del Fiore. This astonishing church is a must-visit in the city.

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 Piazzale Michelangelo, a top-rated observation deck in the city. If you’re up for more discoveries, don’t forget to reserve some time for Siena Cathedral and Piazza Del Campo.

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.

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.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

As the sun sets on another day of adventure, rest up and recharge for the next leg 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 - San Gimignano and Lucca. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Savor the day by visiting some of the best places to see in Siena, including a church, a public square, a monument, a historical landmark and much more! Start your adventure at Chiesa Di Sant'agostino. This up-and-coming church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Dell'anfiteatro located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Guinigi Tower. Its enchanting features will captivate you. After the monument, continue your tour of the village with a visit to St Martin Cathedral. Visitors usually appreciate the breathtaking features of this church. Next up is Piazza Napoleone, a highly recommended public square. For a change of pace, head to Mura Di Lucca. As one of the most intriguing attractions in Siena, this historical landmark is the perfect place to end your self-guided sightseeing tour.

At the end of the day, you will drive to Pisa, 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 Pisa's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Following your dinner, dive into the local bar culture at Bar Mocambo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Tree, the perfect place for those looking to experience the best of the nightlife. Similarly, Chupiteria provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Take some time to reflect on your day and savor another beautiful night in Italy.