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

Day 2 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Start by visiting Galleria Dell'accademia, a prime spot to begin your journey. This photogenic art gallery is sure to impress. Next on your list is Piazza Della Signoria, another must-visit landmark and top-rated public square renowned for its romantic features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Ponte Vecchio. This history-steeped historical landmark is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Uffizi Gallery, a widely recognized art gallery. Nearby, you'll also find Basilica Of Santa Croce In Florence, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazzale Michelangelo and wrap up your day with its romantic appeal.

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.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

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 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 Pisa and Lucca. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Prepare for a day full of family-friendly attractions, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo, Pisa. This timeless public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Leaning Tower Of Pisa, one of the city’s best highlights.

Next, check out Mura Di Lucca, one of the most up-and-coming places to see in Florence. This historical landmark is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Napoleone. Wander around and soak in the awe-inspiring atmosphere this public square offers. Then, head to Porta San Pietro, a top-rated monument that adds another dimension to your day.

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.

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

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Tower Of Mangia is the perfect place to start. This monument is one of the most frequently visited places to visit in Siena. Next, head to Piazza Del Campo, a top-rated public square, known for its visually striking features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Siena Cathedral. This inviting church is a highly recommended experience. Nearby, you'll also find Basilica Of San Domenico and Fortezza Medicea (siena). Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Duomo, a visually striking public square in Siena.

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.

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.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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!