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

On day 2 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Pisa and Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Leaning Tower Of Pisa is must-visit monument and a great option for a daytime tour of the area. Continue your journey to Piazza Del Duomo, Pisa, a globally renowned public square, located just a leisurely stroll away.

Florence’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 1 hour 23 min. Florence welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Basilica Of Santa Croce In Florence, a locally renowned church in Florence. Explore its culturally significant features at your own pace before you continue your journey to your next attraction, Uffizi Gallery. This spectacular art gallery is a top recommendation in the area.

When you’re ready to explore more, Ponte Vecchio is an excellent choice. Spend some time discovering what some claim to be the most enchanting historical landmark in the region. Next, continue your sightseeing at the famous Piazza Della Signoria and discover what makes this public square unique.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax 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.

Enjoy a delicious meal 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.

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

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Florence and Siena. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 1 night.

Whatever your travel style is, Cathedral Of Santa Maria Del Fiore is an essential stop in Florence. This famous church provides an insightful glimpse into the city's identity.

Continue your sightseeing with a visit to Piazzale Michelangelo, a famous observation deck.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 4 min. When you arrive in Siena, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Siena Cathedral and explore the visually striking features. Next, make your way to Piazza Del Campo, another highlight in Siena.

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.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

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.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

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

Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of San Gimignano and Lucca. At the end of the day, enjoy the comforts of a top-rated hotel in Pisa, where you'll spend 1 night.

San Gimignano’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 50 min. San Gimignano welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Chiesa Di Sant'agostino and explore the photogenic features.

Embrace the thrill of the open road as you wave goodbye to San Gimignano and set your GPS to Lucca. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 34 min. Upon reaching Lucca, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

One of our top recommendations for your sightseeing is Piazza Dell'anfiteatro. Spend some time admiring the visually striking features of the public square before you continue to your next stop. Then, head to Guinigi Tower. This underrated monument is a traveler-favorite in the village.

If you're keen to see more, continue to St Martin Cathedral. Feed your curiosity by learning something new about the church. Next, take your journey to Piazza Napoleone, a captivating public square. Conclude your sightseeing at Mura Di Lucca, known for its romantic features.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Pisa. Pisa 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 Pisa's most popular restaurants, and connect with friendly locals for a true cultural experience.

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Unwind after your meal by stepping into Bar Mocambo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Tree offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Chupiteria, another top-rated bar in the area.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.