Relaxed 10-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena and Florence

On day 2 of your relaxed road trip across Italy, you’ll explore the area around Perugia, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Perugia will make you fall even more in love with the city and uniqueness of Italy.

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Perugia. Begin your sightseeing with The Fontana Maggiore. This worthwhile monument is one of the top attractions in the city. Proceed to Piazza Iv Novembre, another must-visit attraction.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to National Archaeological Museum Of Umbria. This beloved museum is a traveler-favorite. Not far away, you’ll find Basilica Of San Francesco D'assisi, another key site on your sightseeing itinerary. Piazza Del Comune is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Basilica Di Santa Chiara and uncover why it's recognized as one of the city's most beloved attractions.

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

Exploring new places makes you hungry. Luckily, Perugia has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Don’t miss out on dining at La Taverna, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Ristorante del Sole, another top spot with a mouthwatering menu. You might also want to secure a reservation at Al Mangiar Bene. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Perugia. The bars in Perugia make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

After enjoying a fulfilling meal, continue your evening at Caffè Fortebraccio, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Caffe Del Banco offers a welcoming atmosphere for easing into the nightlife. Similarly, Dempsey's Perugia provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

Day 3 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll end your day in the city of Siena, where you’ll stay for 3 nights.

Get ready for a day filled with family-friendly attractions, breathtaking views, and picturesque spots in the charming city of Perugia. Your adventure starts at Fortezza Medicea (siena), an increasingly popular local hot spot. Another notable attraction to explore is Battistero Di San Giovanni Battista. This frequently visited church is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Perugia's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Siena Cathedral. This romantic church offers a fascinating experience that many visitors find memorable. Pubblico Palace is also worth visiting, along with Piazza Del Campo. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Tower Of Mangia. This frequently visited monument provides a fitting finale to your sightseeing.

In the city of Siena, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

Exploring new places makes you hungry. Luckily, Siena has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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.

Hang out and unwind at some of the top bars in Siena.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

On day 4 of your relaxed road trip, you’ll start your self-paced adventure in Siena and visit amazing attractions in San Gimignano destinations, just outside of the city. You still have 2 nights left in Siena. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a public square and a museum. Begin your adventure at Piazza Del Duomo. This is an intriguing public square you should not miss. Another must-see is Palazzo Comunale, Pinacoteca, Torre Grossa, an underrated museum in Siena.

When you’re ready for the next sight, head to Sangimignano1300.

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

Exploring the food culture in Siena offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

If you feel like it, head out to a bar to celebrate another fantastic day in Siena and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

Your laid-back and relaxed road trip in Italy continues on day 5, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Siena and beyond. With 1 night left in Siena, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Bring your curiosity for today’s adventure around Siena. Some of the town’s most loved attractions await! Castle Of Verrazzano is the perfect place to start. This castle is one of the most often recommended places to visit in Siena. Next, head to Tumulo Di Montecalvario, a curiosity-inducing archeological site, known for its standout 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 Rocca Di Castellina In Chianti. This visually striking castle is a highly recommended experience. Visit these for an interesting touch to your journey.

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

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Siena, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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.

Experience the amazing nightlife in Siena and unwind at the coolest bars in the city.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Siena!

Day 6 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Florence for 3 nights.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazzale Michelangelo. This spectacular observation deck is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of Santa Croce In Florence, one of the city’s best highlights.

Next, check out Uffizi Gallery, one of the most extraordinary places to see in Siena. This art gallery is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Ponte Vecchio. Wander around and soak in the symbolic atmosphere this historical landmark offers. Then, head to Palazzo Vecchio, a top-rated palace that adds another dimension to your day. Finally, visit the famous Piazza Della Signoria, the last of our attraction recommendations for today.

Continue your laid-back road trip exploration of the best attractions in Italy at Florence. Select from top hotels and accommodations in the city to recharge and rejuvenate.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Florence, explore the city like a local by trying out the best restaurants in the area.

Enjoy a lovely dining experience at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

Day 7 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood 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.

Savor the day by visiting some of the best places to see in Florence, including an art gallery, a food market, a church, a monument and much more! Start your adventure at Galleria Dell'accademia. This popular art gallery is a must-visit for travelers looking for a unique holiday experience. Make your way to Central Market located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Basilica Of San Lorenzo. Its culturally significant features will captivate you. After the church, continue your tour of the city with a visit to Cathedral Of Santa Maria Del Fiore. Visitors usually appreciate the visually striking features of this church. Next up is Giotto's Bell Tower, a highly recommended monument.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Enjoy a lovely dining experience at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Before calling it a day, visit one of the best bars in Florence. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

A leisurely self-drive holiday in Florence can’t get any better than this! Toast to another amazing day in Italy!

On day 8 of your relaxed road trip across Italy, you’ll explore the area around Florence, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Florence will make you fall even more in love with the city and uniqueness of Italy.

Start your adventure at Leaning Tower Of Pisa. This wondrous monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Angelo Caduto located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Pisa Cathedral. Its grand features will captivate you. After the church, continue your tour of the city with a visit to Campo Santo. Visitors usually appreciate the culturally significant features of this cemetery. Next up is Piazza Del Duomo, Pisa, a highly recommended public square.

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

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

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.

Hang out and unwind at some of the top bars in Florence.

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.

Cherish every minute of your relaxed road trip vacation across Italy.