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

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

Florence is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and historic treasures! Start at Galleria Dell'accademia, a locally renowned art gallery that is worthwhile a visit in the city. Nearby, you’ll find Piazza Della Signoria, enchanting visitors with its culturally significant appeal. Continue your exploration at Ponte Vecchio. This historical landmark is one of the city’s most wondrous spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Uffizi Gallery. After exploring the art gallery, head to the well-known Basilica Of Santa Croce In Florence. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazzale Michelangelo, a place of symbolic interest 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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Celebrate another amazing day of your road trip adventure 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Piazza Del Duomo, Pisa. This world-famous public square provides an insightful glimpse into the city's identity. Next, discover Leaning Tower Of Pisa, a historic monument, promising a delightful encounter.

Continue your sightseeing with a visit to Guinigi Tower, a beloved monument. When you’re done, don’t forget to make a stop at the underrated San Michele In Foro. Round off your day at Mura Di Lucca, another gem in Florence with majestic features to discover.

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

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

Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Extend your evening after a delightful meal by visiting Gosh*, which offers the perfect atmosphere for a night out. Moreover, Antico Caffè Del Moro - Art Bar Firenze is another popular option for a drink or two. Likewise, Quelo Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Siena Cathedral, a notable church in the city. Then, head to Piazza Del Campo and soak in the ambiance of this enchanting public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Pubblico Palace. This is one of the city’s most intriguing UNESCO world heritage-listed spots of interest. After exploring the palace, visit the beloved Parco Della Rocca. Not far away, you'll also find Sangimignano1300. This museum is an instagrammable highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazza Del Duomo, an up-and-coming public square in the city.

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.

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.

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.

Savor another day of unforgettable experiences in Italy!

On day 5 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience San Regolo and Castellina in Chianti to the fullest today with this curated day itinerary!

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Castello Di Brolio is the first of them. Spend some time admiring this respected castle before continuing your journey. Tumulo Di Montecalvario is your next stop. This increasingly popular archeological site is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Rocca Di Castellina In Chianti. This culturally significant castle is a sight to behold.

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.

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Charlie Mixology Bar Di Aldinucci Riccardo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Pinacoteca offers an ideal atmosphere to enjoy the pleasures of the night. San Paolo Pub is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 1 night.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a church, a castle, a monument, a public square and much more! Begin your adventure at Basilica Of San Francesco D'assisi. This is a popular church you should not miss. Another must-see is Rocca Maggiore, an underrated castle in Siena.

When you’re ready for the next sight, head to The Fontana Maggiore. From there, take a leisurely stroll to Piazza Iv Novembre, another of the town’s often recommended attractions. We recommend continuing your self-guided tour at Perugia Cathedral, a heritage-rich place of interest in the town.

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.

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 delicious dinner at Tijuana, an excellent option for tonight's dining. Looking for something different? Djària - American Bar offers a tantalizing alternative with its diverse menu. And don’t miss The Florence Irish Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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