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

Day 2 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Catch Galleria Dell'accademia before the crowds roll in. This history-steeped art gallery is sure to ignite your curiosity. Next, dive into the history-steeped features of Piazza Della Signoria, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Ponte Vecchio, a globally renowned historical landmark. For a change of scene, check out Uffizi Gallery, known for its eye-catching features. We also recommend visiting Basilica Of Santa Croce In Florence. This church is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazzale Michelangelo, yet another top-rated attraction in Florence.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

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.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 3 of your road trip, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa and Lucca.

Start your day at Piazza Del Duomo, Pisa. This picture-perfect public square is a globally renowned place to see in Florence. Then, wander over to Leaning Tower Of Pisa. If UNESCO world heritage-designated sites excite you, this monument will be right up your alley. Nearby, you’ll also find Guinigi Tower. This enchanting monument is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, San Michele In Foro is an underrated spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the visually striking Mura Di Lucca. Take a moment to appreciate the fascinating details of this up-and-coming historical landmark.

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

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

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Gosh*, known for its inviting atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another great option if you’re looking for a place to get the night started. Similarly, Quelo Bar provides a great setting to enjoy the night away.

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

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

To truly experience Florence, make sure to drop by Siena Cathedral. This interesting church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Campo, one of the city’s best highlights.

Next, check out Pubblico Palace, one of the most often recommended places to see in Florence. This palace is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Parco Della Rocca. Wander around and soak in the stunning atmosphere this park offers. Then, head to Sangimignano1300, a top-rated museum that adds another dimension to your day. Finally, visit the often recommended Piazza Del Duomo, the last of our attraction recommendations for today.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. Known for great service, it’s a fantastic choice for tonight in Siena.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 5 of your road trip, you'll get the chance to experience San Regolo and Castellina in Chianti. At the end of the day, you'll drive back to Siena, where you still have 1 night left to stay.

San Regolo is brimming with adventures.

Check out the frequently visited castle, Castello Di Brolio. Afterward, continue to Tumulo Di Montecalvario, an archeological site every traveler should visit. As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the hamlet.

Next, make your way to Rocca Di Castellina In Chianti. This worthwhile castle is an essential stop.

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

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.

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to another unforgettable day in Italy!

Dive into day 6 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Santa Maria degli Angeli and Perugia. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Basilica Of San Francesco D'assisi is perfect for a self-paced visit during the day. This historic church is sure to impress. Next on your list is Rocca Maggiore, another must-visit landmark and curiosity-inducing castle renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to The Fontana Maggiore. This breathtaking monument is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Piazza Iv Novembre, a worthwhile public square. Nearby, you'll also find Perugia Cathedral, ready to add charm to your journey.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at Tijuana, 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 Djària - American Bar, 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 The Florence Irish Pub. It’s yet another ideal choice to enhance your time in Florence tonight.

Head back to your accommodation in Florence and get some rest to prepare for another magical day of your road trip in Italy.