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

Day 2 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Piazzale Michelangelo. This spectacular observation deck is a symbolic place to see in Florence. Continue your discovery at Basilica Of Santa Croce In Florence, a heritage-rich church 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 Uffizi Gallery. This top-rated art gallery offers a historic encounter with Florence. Next, make your way to Ponte Vecchio to add another highlight to your day. After that, visit Piazza Della Signoria, a top-rated public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Galleria Dell'accademia, a locally renowned art gallery 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.

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.

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.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Florence is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and photo-friendly spots! Start at Porta San Giovanni, an underrated monument that is worthwhile a visit in the village. Nearby, you’ll find Piazza Del Duomo, enchanting visitors with its inviting appeal. Continue your exploration at Palazzo Comunale, Pinacoteca, Torre Grossa. This museum is one of the village’s most locally appreciated 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 Rocca Di Montestaffoli. After exploring the castle, head to the locally appreciated Parco Della Rocca.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

Make sure to reserve a table at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

On day 4 of your road trip, you will have an entire day to explore Siena. You’ll stay in Siena for 1 night and discover all the best things to see and do in the area.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a palace, a monument, a public square, a church and much more! Begin your adventure at Pubblico Palace. This is a locally appreciated palace you should not miss. Another must-see is Tower Of Mangia, a frequently visited monument in Siena.

When you’re ready for the next sight, head to Piazza Del Campo. From there, take a leisurely stroll to Siena Cathedral, another of the city’s well-known attractions. We recommend continuing your self-guided tour at Basilica Of San Domenico, a picture-perfect place of interest in the city. If time allows, add Fortezza Medicea (siena) to your itinerary. This increasingly popular monument offers the perfect finishing touch to your day in Siena.

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 explore more of Siena, 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.

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.

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.

Get a good night's sleep and look forward to another great day on the road in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pienza and San Quirico d'Orcia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pienza, which will be your home away from home for 2 nights.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Palazzo Piccolomini, Pienza. This visually striking palace is sure to ignite your curiosity. Next, dive into the romantic features of Cipressi Di San Quirico D'orcia, a must-visit rock formation in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Chapel Vitaleta, an up-and-coming church.

At the end of the day, you will drive to Pienza, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you explore more of Pienza, 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.

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

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Pienza for your remaining 1 night in the village 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 Montepulciano, Montalcino, and Castelnuovo dell'Abate.

Enjoy the perfect balance of relaxation and exploration in Pienza today. One of the most up-and-coming attractions included on the itinerary is Porta Al Prato. This heritage-rich monument will help you start your sightseeing on top. Then, take a leisurely stroll to Fortezza Medicea and learn what makes this history-steeped castle unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the curiosity-inducing Fortress Of Montalcino. After exploring the castle, head to Abbey Of Sant'antimo. This curiosity-inducing monastery is a highlight in Pienza.

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

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

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Arezzo. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Get ready to discover some of the most iconic wonders in Pienza, including a church, a museum, and a public square. Start your day at San Francesco, Arezzo. This culturally significant church is an increasingly popular place to see in Pienza. Then, wander over to Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi. If history-steeped sites excite you, this museum will be right up your alley. Nearby, you’ll also find Piazza Grande. This history-steeped public square is a favorite among visitors.

Pienza offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Arezzo Cathedral is an increasingly popular spot in the city that will captivate you with its unique charm.

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.

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 Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

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