11-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena, Perugia, and Orvieto

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

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at The Boboli Gardens. This captivating botanical garden is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Ponte Vecchio, one of the city’s most promising highlights.

Next, check out Uffizi Gallery, one of the most impressive places to see in Florence. This art gallery is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Palazzo Vecchio. Wander around and soak in the enchanting atmosphere this palace offers. Finally, take the path to the impressive Piazza Della Signoria, the last of our attraction recommendations for today.

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 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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 3 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Today’s itinerary in Florence covers several incredible sights, including a public square, a church, a monument, a historical landmark and much more! Start your adventure at Piazza Del Duomo, Pisa. This world-famous public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the grand wonders of Pisa Cathedral, 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 Leaning Tower Of Pisa. This timeless monument offers an enriching experience. For a change of pace, head to Guinigi Tower, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to San Michele In Foro. This stunning church offers a fulfilling end to a perfect day.

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

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

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

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

On day 4 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 Siena. In the evening, you’ll end up in Siena, where you will stay for 3 nights.

Today’s agenda in Florence includes a monument, a church, a palace, a public square and much more! Fortezza Medicea (siena) is must-visit monument and a great starting point for the day. Next, continue your journey to Basilica Of San Domenico, a beloved church, located just a leisurely stroll away. Next, head to Siena Cathedral, a stunning church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. If you’re looking for more, Pubblico Palace is also an often recommended attraction that is worthwhile a visit. Lastly, don’t miss Piazza Del Campo, a widely recognized gem to see in the city.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.

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 your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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

On day 5 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in San Gimignano and Volterra. You still have 2 nights left in Siena.

Today, you'll explore some of the most beautiful places in Siena, including a monument, a public square, a museum, a park and much more! Start your day with a visit to Porta San Giovanni. This worthwhile monument is a must-visit in the village. When you’re ready for your next discovery, continue to Piazza Del Duomo, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Palazzo Comunale, Pinacoteca, Torre Grossa, a frequently visited museum in the village. If you’re up for more discoveries, don’t forget to reserve some time for Parco Della Rocca and Etruscan Museum "mario Guarnacci".

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.

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.

Unwind after your meal by stepping into Charlie Mixology Bar Di Aldinucci Riccardo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Pinacoteca offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook San Paolo Pub, another top-rated bar in the area.

Raise your glass and celebrate another amazing 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 Siena for your remaining 1 night in the city 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 San Donato in Poggio, Castellina in Chianti, and San Regolo.

A blend of family-friendly attractions, breathtaking views, and photo-friendly spots await you in Siena on today’s itinerary. First up is the locally appreciated astronomical observatory, Osservatorio Polifunzionale Del Chianti. Afterward, continue to Rocca Di Castellina In Chianti.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Castello Di Brolio. This increasingly popular castle is an essential stop that should not be missed.

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

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.

Treat yourself to a delicious dinner at Ristorante San Desiderio, an excellent option for tonight's dining. Looking for something different? Osteria Le Logge offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Taverna Di Cecco. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Raise your glass to another unforgettable day in Italy!

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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 Perugia. You’ll stay here for 1 night.

Today, you'll explore some of the most beautiful places in Siena, including a church, a castle, a historical landmark, a public square, a monument and much more! Start your day with a visit to Basilica Of San Francesco D'assisi. This well-known church is a must-visit in the town. When you’re ready for your next discovery, continue to Rocca Maggiore, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Acquedotto Medievale Di Perugia, a curiosity-inducing historical landmark in the town. If you’re up for more discoveries, don’t forget to reserve some time for Perugia Cathedral and Piazza Iv Novembre.

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

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

Have a fantastic dining experience at Ristorante Settimo Sigillo, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffè Baglioni offers an enticing alternative with its varied menu. Additionally, Bar Pellas is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Perugia.

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

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Orvieto, which will be your home away from home for 2 nights.

Enjoy the perfect balance of relaxation and exploration in Perugia today. One of the most popular attractions included on the itinerary is Orvieto Cathedral. This enchanting church will help you start your sightseeing on top. Then, take a leisurely stroll to Orvieto Underground and learn what makes this instagrammable cave system unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile Torre Del Moro Orvieto. After exploring the monument, head to Pozzo Della Cava. This beloved cave is a highlight in Perugia.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Duomo stands out as an excellent choice for a post-dinner cocktail.

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

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

A visit to Via dei Condotti in Rome is a must on your agenda today. This street is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Today's adventure in Orvieto promises more breathtaking discoveries and enriching experiences! Begin at Colosseum. This picture-perfect archeological site is a highlight of any visit in the city. Then, enjoy Roman Forum, another historic attraction that never fails to captivate visitors. Next, head over to Trevi Fountain, one of the city’s most timeless attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Navona, a timeless public square, and take a stroll around the area.

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

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

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Cortona. 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.

Bring your curiosity for today’s adventure around Orvieto. Some of the town’s most loved attractions await. Parterre is the perfect place to start. This park is one of the most beloved places to visit in Orvieto. Next, head to Basilica Of Saint Margaret Of Cortona, an intriguing church, known for its breathtaking 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 Hermitage "le Celle". This history-steeped monastery offers a unique experience that is highly recommended.

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.

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.

Enjoy a delicious meal at Tijuana, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Djària - American Bar, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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.