7-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena

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

Start by visiting Galleria Dell'accademia, a prime spot to begin your journey. This heritage-rich art gallery is sure to impress. Next on your list is Piazza Della Signoria, another must-visit landmark and spectacular public square renowned for its culturally significant 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 visually striking 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.

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

A blend of family-friendly attractions, breathtaking views, and photo-friendly spots await you in Florence 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 Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Guinigi Tower. This often recommended monument is an essential stop. Following that, head to San Michele In Foro, another must-visit site that will enhance your experience. Don’t forget to stop by Mura Di Lucca, an increasingly popular historical landmark in the city.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

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

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

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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 Siena and San Gimignano. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Siena Cathedral. This well-known church provides an insightful glimpse into the city's identity. Next, discover Piazza Del Campo, a history-steeped public square, promising a delightful encounter.

Continue your sightseeing with a visit to Pubblico Palace, an up-and-coming palace. When you’re done, don’t forget to make a stop at the increasingly popular Parco Della Rocca. Not far away from the park, you will find the inviting Piazza Del Duomo, perfect for a quick visit. Round off your day at Sangimignano1300, another gem in Florence with photogenic features to discover.

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.

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

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena 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!

On day 5 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 Regolo and Castellina in Chianti. You still have 1 night left in Siena.

Bring your curiosity for today’s adventure around Siena. Some of the hamlet’s most loved attractions await! Castello Di Brolio is the perfect place to start. This castle is one of the most beloved places to visit in Siena. Next, head to Tumulo Di Montecalvario, a beloved archeological site, known for its history-steeped 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 Rocca Di Castellina In Chianti. This visually striking castle is a highly recommended experience. Visit these for an interesting touch to your journey.

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

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

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.

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 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Santa Maria degli Angeli and Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Basilica Of San Francesco D'assisi. This breathtaking church is a highlight of any visit in the town. Then, enjoy Rocca Maggiore, another visually striking attraction that never fails to captivate visitors. Next, head over to The Fontana Maggiore, one of the town’s most frequently visited attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Iv Novembre. This enchanting public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Perugia Cathedral, a locally appreciated church, and take a stroll around the area.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence 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 Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Make sure to reserve a table at Tijuana, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Djària - American Bar, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of The Florence Irish Pub, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Get a good night's sleep and look forward to another great day on the road in Italy!