6-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling west to Siena

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Don’t miss Oltrarno in Florence today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Piazzale Michelangelo, a famous observation deck in the city. Then, head to Basilica Of Santa Croce In Florence and soak in the ambiance of this photogenic church.

There are many interesting places to see in Florence, and when you are ready for more, go to Piazza Della Signoria. This is one of the city’s most impressive remarkable spots of interest. After exploring the public square, visit the spectacular Uffizi Gallery. Not far away, you'll also find Ponte Vecchio. This historical landmark is a romantic highlight in Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 delicious meal 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.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Get a good night's sleep and look forward to another great day on the road 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 Siena. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Prepare for a day full of family-friendly attractions, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea (siena). This intriguing monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of San Domenico, one of the city’s best highlights.

Next, check out Siena Cathedral, one of the most interesting places to see in Florence. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pubblico Palace. Wander around and soak in the culturally significant atmosphere this palace offers. Then, head to Piazza Del Campo, a top-rated public square that adds another dimension to your day. Finally, visit the worthwhile Tower Of Mangia, the last of our attraction recommendations for today.

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

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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.

On day 4 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in San Gimignano, Greve in Chianti, and Greti. You still have 1 night left in Siena.

Discover a day packed with fun adventures, breathtaking views, and picturesque spots in Siena. Begin your sightseeing with Porta San Giovanni. This up-and-coming monument is one of the top attractions in the village. Proceed to Piazza Del Duomo, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Palazzo Comunale, Pinacoteca, Torre Grossa. This worthwhile museum is a traveler-favorite. Not far away, you’ll find Chiesa Di Sant'agostino, another key site on your sightseeing itinerary. Castle Of Verrazzano is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Villa Calcinaia - Conti Capponi and uncover why it's recognized as one of the village's most frequently visited attractions.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Siena.

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 delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Charlie Mixology Bar Di Aldinucci Riccardo, known for its inviting atmosphere. Bar Pinacoteca is another great option if you’re looking for a place to get the night started. Similarly, San Paolo Pub provides a great setting to enjoy the night away.

Say good night to Siena and look forward to another great day of your road trip in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Lucca. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

A blend of fun adventures, breathtaking views, and picturesque spots await you in Siena on today’s itinerary. First up is the timeless public square, Piazza Del Duomo, Pisa. Afterward, continue to Leaning Tower Of Pisa, a monument every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Mura Di Lucca. This up-and-coming historical landmark is an essential stop. Following that, head to Porta San Pietro, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Dell'anfiteatro, an interesting public square in the city.

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

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

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!