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.

Today’s route brings fun adventures, picturesque spots, and history-rich sites. The first attraction of today is Galleria Dell'accademia. This locally renowned art gallery is a detailed place to see in Florence. Continue your discovery at Piazza Della Signoria, a romantic public square with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Ponte Vecchio. This wondrous historical landmark offers a history-steeped encounter with Florence. Next, make your way to Uffizi Gallery to add another highlight to your day. After that, visit Basilica Of Santa Croce In Florence, a popular church that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazzale Michelangelo, a famous observation deck in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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 you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip 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!

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Piazza Del Duomo, Pisa, a timeless public square in the city. Then, head to Leaning Tower Of Pisa and soak in the ambiance of this breathtaking monument.

There are many interesting places to see in Florence, and when you are ready for more, go to Guinigi Tower. This is one of the city’s most worthwhile culturally significant spots of interest. After exploring the monument, visit the worthwhile San Michele In Foro. Not far away, you'll also find Mura Di Lucca. This historical landmark is an enchanting highlight in Florence.

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.

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

After your meal, keep the night alive at a bar like Gosh*, known for its lively atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Quelo Bar offers an excellent atmosphere for those looking to amp up the evening.

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, 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 Siena. You’ll stay here for 2 nights.

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a palace, a park, a museum and much more! Start your adventure at Siena Cathedral. This popular church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Piazza Del Campo, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Pubblico Palace. This underrated palace offers an enriching experience. For a change of pace, head to Parco Della Rocca, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Sangimignano1300 and Piazza Del Duomo. These sights offer a fulfilling end to a perfect day.

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

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

If you’re not ready to end the night just yet, Meet Life Cafè offers a perfect venue to relax and savor a drink. Similarly, Maudit Pub is well-suited for those looking to unwind in a social setting. Bar Impero Siena is another excellent spot to enjoy a nightcap after a delightful meal.

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 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Castello Di Brolio. This underrated castle provides an insightful glimpse into the hamlet's identity. Next, discover Tumulo Di Montecalvario, a photogenic archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Rocca Di Castellina In Chianti, an up-and-coming castle.

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

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.

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.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly spots. 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. Basilica Of San Francesco D'assisi is the first of them. Spend some time admiring this historic church before continuing your journey. Rocca Maggiore is your next stop. This frequently visited castle 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 The Fontana Maggiore. This culturally significant monument is a sight to behold. To round off your sightseeing experience, visit Piazza Iv Novembre and Perugia Cathedral.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

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

Treat yourself to a wonderful meal at Tijuana, a top-rated dining spot in Florence. If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu. You might also want to book a table at The Florence Irish Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.