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

Day 2 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, photo-friendly spots, and historic treasures. Start at Galleria Dell'accademia, a locally renowned art gallery in the city. Then, head to Piazza Della Signoria and soak in the ambiance of this masterful public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Ponte Vecchio. This is one of the city’s most wondrous respected spots of interest. After exploring the historical landmark, visit the spectacular Uffizi Gallery. Not far away, you'll also find Basilica Of Santa Croce In Florence. This church is a culturally significant highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazzale Michelangelo, a spectacular observation deck in the city.

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.

Don’t miss out on dining 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.

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.

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, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Discover a day packed with family-friendly attractions, scenic views, and photo-friendly spots in Florence. Begin your sightseeing with Piazza Del Duomo, Pisa. This globally renowned public square is one of the top attractions in the city. Proceed to Leaning Tower Of Pisa, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Guinigi Tower. This increasingly popular monument is a traveler-favorite. Not far away, you’ll find San Michele In Foro, another key site on your sightseeing itinerary. Mura Di Lucca is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

As you explore more of Florence, 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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences 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 - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Today, you'll explore some of the most beautiful places in Florence, including a church, a public square, a palace, a park, a museum and much more! Start your day with a visit to Siena Cathedral. This notable church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Campo, which may be one of the most history-steeped places you will experience today.

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 Pubblico Palace, an intriguing palace in the city. If you’re up for more discoveries, don’t forget to reserve some time for Parco Della Rocca and Sangimignano1300. End your day with a visit to Piazza Del Duomo, a locally appreciated public square that’s sure to leave a lasting impression.

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.

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

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Relax and recharge in preparation for another adventurous day in Italy!

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in San Regolo and Castellina in Chianti.

Today’s agenda in Siena includes a castle and an archeological site. Castello Di Brolio is must-visit castle and a great starting point for the day. Next, continue your journey to Tumulo Di Montecalvario, an intriguing archeological site, located just a leisurely stroll away. Next, head to Rocca Di Castellina In Chianti, a visually striking castle, also available for your discovery today.

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

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

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Charlie Mixology Bar Di Aldinucci Riccardo, a well-loved spot among locals and tourists. Or, head to Bar Pinacoteca. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at San Paolo Pub, another top-rated place in the area.

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

On day 6 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 Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Get ready for a day filled with family-friendly attractions, breathtaking views, and picturesque spots in the charming town of Siena. Your adventure starts at Basilica Of San Francesco D'assisi, a popular local hot spot. Another notable attraction to explore is Rocca Maggiore. This beloved castle is known for its picture-perfect appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to The Fontana Maggiore. This masterful monument offers a fascinating experience that many visitors find memorable. Piazza Iv Novembre is also worth visiting, along with Perugia Cathedral. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

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

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Savor another day of unforgettable experiences in Italy!