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

Day 2 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Florence covers several incredible sights, including an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Start your adventure at Piazzale Michelangelo. This top-rated observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Basilica Of Santa Croce In Florence, a must-see church 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 Uffizi Gallery. This widely recognized art gallery offers an enriching experience. For a change of pace, head to Ponte Vecchio, where you can take in respected features. Conclude your self-guided sightseeing tour with a visit to Piazza Della Signoria and Galleria Dell'accademia. These sights offer a fulfilling end to a perfect day.

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.

Experience shopping bliss at Florence as you explore Via de' Tornabuoni. Take a leisurely stroll through unique boutiques and high-end shops, where local treasures are waiting to be found. Beyond shopping, Via de' Tornabuoni offers more options, including unique attractions, key services, and vibrant events.

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.

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 your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass and celebrate another amazing 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.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a public square, a museum, a castle, a park and much more! Begin your adventure at Porta San Giovanni. This is a frequently visited monument you should not miss. Another must-see is Piazza Del Duomo, a curiosity-inducing public square in Florence.

When you’re ready for the next sight, head to Palazzo Comunale, Pinacoteca, Torre Grossa. From there, take a leisurely stroll to Rocca Di Montestaffoli, another of the village’s locally appreciated attractions. We recommend continuing your self-guided tour at Parco Della Rocca, a romantic place of interest in the village.

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 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 dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 4 of your road trip across Italy promises a magnificent time exploring Siena. You have 1 night left in Siena. Take the opportunity to experience more of the best attractions and activities in the city.

Set out on a day brimming with family-friendly attractions, scenic views, and photo-friendly spots. Start at the curiosity-inducing Pubblico Palace, a historic palace in Siena. Next, go to Tower Of Mangia.

After visiting Pubblico Palace and Tower Of Mangia, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Campo. This romantic public square offers a unique experience. Siena Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Basilica Of San Domenico, one of the most stunning places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by Fortezza Medicea (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.

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 Osteria Quattro Venti, a top-rated dining spot in Siena. If you're in the mood for something new, try Fischi per Fiaschi, another premier location with a delectable menu. You might also want to book a table at Osteria da Divo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Explore the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Pinacoteca for a great selection of flavorful drinks and a charming setting. Furthermore, San Paolo Pub is perfect for those looking to extend their night with a touch of local flavor.

Savor another day of unforgettable experiences 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.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most locally appreciated attractions included on the itinerary is Palazzo Piccolomini, Pienza. This romantic palace will help you start your sightseeing on top. Then, take a leisurely stroll to Cipressi Di San Quirico D'orcia and learn what makes this peaceful rock formation unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile Chapel Vitaleta.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Pienza. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

On day 6 of your road trip, you’ll start and end your day in Pienza, but spend part of the day exploring places of interest outside the immediate village. On today's itinerary, you'll find attractions in Montepulciano, Montalcino, and Castelnuovo dell'Abate. You still have 1 night left in Pienza.

Brace yourself for today’s incredible lineup of attractions in Pienza, featuring fun adventures, photo-friendly spots, and history-rich sites. Start at Porta Al Prato, an increasingly popular monument in the town. Then, head to Fortezza Medicea and soak in the ambiance of this enchanting castle.

There are many interesting places to see in Pienza, and when you are ready for more, go to Fortress Of Montalcino. This is one of the town’s most beloved enchanting spots of interest. After exploring the castle, visit the underrated Abbey Of Sant'antimo.

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

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.

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

On day 7 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Arezzo. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Set out on a day brimming with fun adventures, photo-friendly spots, and history-rich sites. Start at the locally appreciated San Francesco, Arezzo, a photogenic church in Pienza. Next, go to Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi.

After visiting San Francesco, Arezzo and Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi, have a stroll along Pienza's streets and take in the local charm. Continue your sightseeing by heading to Piazza Grande. This history-steeped public square offers a unique experience. Arezzo Cathedral is another noteworthy attraction worthwhile a 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 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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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.

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