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

On day 2 of your relaxed road trip, you’ll start your self-paced adventure in Perugia and visit amazing attractions in Perugia and Santa Maria degli Angeli destinations, just outside of the city. You still have 1 night left in Perugia. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Enjoy the perfect balance of relaxation and exploration in Perugia today. One of the most often recommended attractions included on the itinerary is The Fontana Maggiore. This historic monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Iv Novembre and learn what makes this grand public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the often recommended National Archaeological Museum Of Umbria. After exploring the museum, head to Basilica Of San Francesco D'assisi. This locally renowned church is a highlight in Perugia. As your day continues, stop by Piazza Del Comune, known for its history-steeped features. Lastly, don’t forget to check out the beloved Basilica Di Santa Chiara. Enjoy exploring this incredible church at your own pace.

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

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 Perugia, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Make sure to reserve a table at La Taverna, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante del Sole, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Al Mangiar Bene, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Keep the evening going at Caffè Fortebraccio, a great choice for enjoying the after-dinner hours with a drink. You could also go to Caffe Del Banco, which offers a similarly pleasant setting and great drinks. Another option is Dempsey's Perugia, which provides an inviting environment for unwinding after a busy day out.

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.

Day 3 of your relaxed road trip across the beautiful country of Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This historic monument is sure to impress. Next on your list is Battistero Di San Giovanni Battista, another must-visit landmark and intriguing church renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Perugia by sampling some local delicacies. When you’re ready for more sightseeing, head to Siena Cathedral. This visually striking church is an essential place to visit for anyone looking for the full Perugia experience. We also recommend visiting Pubblico Palace, a locally appreciated palace. Nearby, you'll also find Piazza Del Campo, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Tower Of Mangia and wrap up your day with its historic appeal.

You’ll be staying at the incredible city of Siena in this laid-back road trip in Italy. You'll stay here for 3 nights.

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.

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

Toast to another unforgettable and relaxing road trip adventure in Italy!

Your laid-back and relaxed road trip in Italy continues on day 4, 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 2 nights left in Siena, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo. This frequently visited public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Palazzo Comunale, Pinacoteca, Torre Grossa, one of the village’s best highlights.

Next, check out Sangimignano1300, one of the most beloved places to see in Siena. This museum is a favorite among locals and travelers alike.

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

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.

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

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

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 5 of your relaxed road trip across Italy, you’ll explore the area around Siena, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Siena will make you fall even more in love with the city and uniqueness of Italy.

Siena is brimming with adventures. Today’s wonderful stops include a castle and an archeological site. Begin your sightseeing adventure at the up-and-coming Castle Of Verrazzano and allow yourself time to explore. Just a short distance away you'll find your next stop, Tumulo Di Montecalvario, a symbolic archeological site that draws visitors from far and near.

Continue your journey to Rocca Di Castellina In Chianti, one of the town’s most curiosity-inducing spots that you shouldn’t miss.

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

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 Siena.

Don’t miss out on dining at Ristorante San Desiderio, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Le Logge, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena 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 Siena. The bars in Siena make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Toast to another unforgettable and relaxing road trip adventure in Italy!

Day 6 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Florence. By the end of the day, you’ll drive in the direction of the city of Florence, where you’ll stay at a top-rated hotel of your choice for 3 nights.

Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Piazzale Michelangelo. This extraordinary 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 impressive 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 romantic 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.

After a day of exploration, relax at one of the top hotels or accommodations in Florence. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

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.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass and relax after another big day of your leisurely paced road trip 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 top thing to do today is to explore Oltrarno, a must-see neighborhood in Florence. It's the perfect starting point for touring the top attractions in the area.

Get ready for a day filled with family-friendly attractions, photo-friendly spots, and history-rich sites in the charming city of Florence. Your adventure starts at Galleria Dell'accademia, a notable local hot spot. Another notable attraction to explore is Central Market. This interesting food market is known for its eye-catching appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Of San Lorenzo. This culturally significant church offers a fascinating experience that many visitors find memorable. Cathedral Of Santa Maria Del Fiore is also worth visiting, along with Giotto's Bell Tower. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Florence offers a wide selection of experiences for every traveler.

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

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

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.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

On day 8 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in Pisa destinations, just outside of the city. You still have 1 night left in Florence. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Start by visiting Leaning Tower Of Pisa, a prime spot to begin your journey. This breathtaking monument is sure to impress.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Pisa Cathedral. This culturally significant church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Campo Santo, an up-and-coming cemetery. Nearby, you'll also find Piazza Del Duomo, Pisa, ready to add charm to your journey.

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

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 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.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

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.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across Italy.