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

Day 2 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

A blend of fun adventures, romantic experiences, and scenic views await you in Florence on today’s itinerary. First up is the spectacular observation deck, Piazzale Michelangelo. Afterward, continue to Basilica Of Santa Croce In Florence, a church every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Uffizi Gallery. This extraordinary art gallery is an essential stop. Following that, head to Ponte Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Della Signoria, a spectacular public square in the city. Finally, end your day with a visit to Galleria Dell'accademia, an eye-catching art gallery that offers the perfect conclusion to your sightseeing of the 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.

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Bring your curiosity for today’s adventure around Florence. Some of the village’s most loved attractions await! Porta San Giovanni is the perfect place to start. This monument is one of the most increasingly popular places to visit in Florence. Next, head to Piazza Del Duomo, a curiosity-inducing public square, known for its history-steeped 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 Palazzo Comunale, Pinacoteca, Torre Grossa. This picture-perfect museum is a highly recommended experience. Nearby, you'll also find Rocca Di Montestaffoli and Parco Della Rocca. Visit these for an interesting touch to your journey.

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.

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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

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.

Raise your glass and celebrate another amazing 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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Pubblico Palace, an intriguing palace in the city. Then, head to Tower Of Mangia and soak in the ambiance of this UNESCO world heritage-designated monument.

There are many interesting places to see in Siena, and when you are ready for more, go to Piazza Del Campo. This is one of the city’s most astonishing history-steeped spots of interest. After exploring the public square, visit the popular Siena Cathedral. Not far away, you'll also find Basilica Of San Domenico. This church is a stunning highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Fortezza Medicea (siena), a locally appreciated monument in the city.

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 Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining 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.

To truly maximize your evening out, consider visiting Charlie Mixology Bar Di Aldinucci Riccardo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Pinacoteca, another bar with an inviting ambiance. Similarly, San Paolo Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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.

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Pienza and San Quirico d'Orcia, 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 Pienza. You’ll stay here for 2 nights.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Palazzo Piccolomini, Pienza. This underrated palace is a visually striking place to see in Siena. Continue your discovery at Cipressi Di San Quirico D'orcia, an eye-catching rock formation with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Chapel Vitaleta. This intriguing church offers a romantic encounter with Siena. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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.

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

Savor another day of unforgettable experiences in Italy!

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.

Today’s route brings family-friendly attractions, photo-friendly spots, and historic treasures. The first attraction of today is Porta Al Prato. This up-and-coming monument is a heritage-rich place to see in Pienza. Continue your discovery at Fortezza Medicea, a history-steeped castle with stories to tell.

As you stroll around Pienza, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Fortress Of Montalcino. This up-and-coming castle offers an awe-inspiring encounter with Pienza. Next, make your way to Abbey Of Sant'antimo to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Pienza.

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

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

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

Enjoy the perfect balance of relaxation and exploration in Pienza today. One of the most increasingly popular attractions included on the itinerary is San Francesco, Arezzo. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Fondazione Ivan Bruschi - Casa Museo Dell'antiquariato Ivan Bruschi and learn what makes this photogenic museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally renowned Piazza Grande. After exploring the public square, head to Arezzo Cathedral. This frequently visited church is a highlight in Pienza.

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.

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.

Treat yourself to a delightful dinner at Ristorante Buca Mario, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Agricola Toscana? It's another excellent option with a diverse menu. Consider reserving a table at Eataly Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.