One-Week Italy Self-Drive Road Trip With Itinerary from Florence traveling south to Siena and Pienza

Day 2 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Piazzale Michelangelo leaves a lasting impression. This observation deck is one of the most spectacular places to visit in Florence. Next, head to Basilica Of Santa Croce In Florence, a notable church, known for its culturally significant 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 Uffizi Gallery. This picture-perfect art gallery is a highly recommended experience. Nearby, you'll also find Ponte Vecchio and Piazza Della Signoria Visit these for an interesting touch to your journey. Finish the day with a visit to Galleria Dell'accademia, a detailed art gallery 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 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.

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.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Celebrate another amazing day of your road trip adventure in Italy!

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of San Gimignano. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 2 nights.

Set your GPS to San Gimignano and hit the road. Expect a journey of approximately 1 hour without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Our first attraction recommendation in San Gimignano is Porta San Giovanni, a curiosity-inducing monument that draws attention for its culturally significant features. Spend some time soaking in the atmosphere before continuing to Piazza Del Duomo, an UNESCO world heritage-designated public square that stands out in the village.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Palazzo Comunale, Pinacoteca, Torre Grossa, a curiosity-inducing museum that offers a unique experience. Be sure to also explore Rocca Di Montestaffoli, a nearby castle, highly recommended by other travelers. End your self-guided tour at Parco Della Rocca, a romantic park and the perfect final attraction in San Gimignano.

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

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.

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.

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

Day 4 of your road trip will take you to the best attractions Siena has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Siena.

One of the most frequently visited attractions included on the itinerary is Pubblico Palace. This picture-perfect palace will help you start your sightseeing on top. Then, take a leisurely stroll to Tower Of Mangia and learn what makes this culturally significant monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the extraordinary Piazza Del Campo. After exploring the public square, head to Siena Cathedral. This locally renowned church is a highlight in Siena. As your day continues, stop by Basilica Of San Domenico, known for its breathtaking features. Lastly, don’t forget to check out the increasingly popular Fortezza Medicea (siena). Enjoy exploring this incredible monument at your own pace.

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.

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Make sure to reserve a table at Osteria Quattro Venti, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Fischi per Fiaschi, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pinacoteca, a bar catering to every mood and preference. San Paolo Pub likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Pienza and San Quirico d'Orcia. At the end of the day, you will retreat to the hotel of your choice in Pienza, where will spend 2 nights.

Continue your road trip and head to your next destination, Pienza. This car ride takes around 1 hour 5 min.

Spend your afternoon discovering Palazzo Piccolomini, Pienza, a locally appreciated palace known for its romantic features.

Continue your road trip and head to your next destination, San Quirico d'Orcia.

For a more meaningful self-guided tour of the village's best attractions, visit Cipressi Di San Quirico D'orcia, a beloved rock formation that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Chapel Vitaleta and admire its enchanting features.

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

Pienza is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Pienza.

Celebrate another amazing day of your road trip adventure in Italy!

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Montepulciano, Montalcino, and Castelnuovo dell'Abate. With 1 night to stay in Pienza, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!

After soaking in Pienza’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Montepulciano. Expect your car journey to take a minimum of 19 min. When you arrive in Montepulciano, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Porta Al Prato, an often recommended monument that everyone visiting Montepulciano should see. Next, head to Fortezza Medicea. This enchanting castle is one of the most beloved attractions in the region.

Set your GPS to Montalcino and hit the road. Expect a journey of approximately 42 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Montalcino beckons with new experiences!

When you're ready for some sights, head to Fortress Of Montalcino, an increasingly popular castle in Montalcino. Explore its history-steeped features at your own pace before you continue your journey.

When you’re ready to jump back into the car and say goodbye to Montalcino, you’ll hit the road in the direction of Castelnuovo dell'Abate. This drive usually takes around 13 min.

Our first attraction recommendation in Castelnuovo dell'Abate is Abbey Of Sant'antimo, a locally appreciated monastery that draws attention for its romantic features.

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

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 Pienza, it's often a good idea to reserve a table in advance.

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

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Arezzo. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Pienza and set your GPS to Arezzo. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 8 min. Upon reaching Arezzo, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

For a more meaningful self-guided tour of the city's best attractions, visit San Francesco, Arezzo, a curiosity-inducing church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi and admire its standout features.

When you’re ready, continue to Piazza Grande, a locally renowned public square beloved by locals and tourists alike. Don't miss out on Arezzo Cathedral, another highlight of the area that promises a memorable visit.

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.

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.

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!