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

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the top-rated Piazzale Michelangelo, an enchanting observation deck in Florence. Next, go to Basilica Of Santa Croce In Florence.

After visiting Piazzale Michelangelo and Basilica Of Santa Croce In Florence, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Uffizi Gallery. This romantic art gallery offers a unique experience. Ponte Vecchio is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Della Signoria, one of the most grand places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Galleria Dell'accademia.

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.

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 delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

Dive into day 3 of your remarkable road trip in Italy. Today you will explore 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.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most often recommended attractions included on the itinerary is Porta San Giovanni. This historic monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo and learn what makes this history-steeped public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the increasingly popular Palazzo Comunale, Pinacoteca, Torre Grossa. After exploring the museum, head to Rocca Di Montestaffoli. This intriguing castle is a highlight in Florence. As your day continues, stop by Parco Della Rocca, known for its romantic features.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and celebrate another amazing day of your road trip 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 Siena by discovering the best things there are to see and do in the city.

Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming city of Siena. Your adventure starts at Pubblico Palace, a locally appreciated local hot spot. Another notable attraction to explore is Tower Of Mangia. This up-and-coming monument is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Del Campo. This romantic public square offers a fascinating experience that many visitors find memorable. Siena Cathedral is also worth visiting, along with Basilica Of San Domenico. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Fortezza Medicea (siena). This increasingly popular monument provides a fitting finale to your sightseeing.

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.

Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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.

Take some time to reflect on your day and savor another beautiful night 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 vibrant destinations - Pienza and San Quirico d'Orcia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pienza. You will spend 2 nights here for some well-deserved relaxation.

Today’s itinerary in Siena covers several incredible sights, including a palace, a rock formation, and a church. Start your adventure at Palazzo Piccolomini, Pienza. This frequently visited palace is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the stunning wonders of Cipressi Di San Quirico D'orcia, a must-see rock formation in the village.

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 Chapel Vitaleta. This underrated church offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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

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

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

At the end of the day, you'll drive back to Pienza, where you'll stay for 1 night more.

Prepare for a day full of fun adventures, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Porta Al Prato. This beloved monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Fortezza Medicea, one of the town’s best highlights.

Next, check out Fortress Of Montalcino, one of the most locally appreciated places to see in Pienza. This castle is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Abbey Of Sant'antimo. Wander around and soak in the inviting atmosphere this monastery offers.

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

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 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.

Brace yourself for today’s incredible lineup of attractions in Pienza, featuring fun adventures, photo-friendly spots, and historic treasures. Start at San Francesco, Arezzo, a beloved church in the city. Then, head to Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi and soak in the ambiance of this visually striking museum.

There are many interesting places to see in Pienza, and when you are ready for more, go to Piazza Grande. This is one of the city’s most well-known romantic spots of interest. After exploring the public square, visit the frequently visited Arezzo Cathedral.

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 and reflect on the day's adventures.

Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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.

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.