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

Your laid-back and relaxed road trip in Italy continues on day 2, 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 Perugia and beyond. With 1 night left in Perugia, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Immerse yourself in Perugia’s rich culture with today's sightseeing itinerary. Start your journey at The Fontana Maggiore. This picture-perfect monument is sure to ignite your curiosity. Next, dive into the enchanting features of Piazza Iv Novembre, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to National Archaeological Museum Of Umbria, an underrated museum. For a change of scene, check out Basilica Of San Francesco D'assisi, known for its historic features. We also recommend visiting Piazza Del Comune. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Basilica Di Santa Chiara, yet another increasingly popular attraction in Perugia.

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

Exploring the food culture in Perugia 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 delicious meal 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, stop at some of Perugia’s best bars to celebrate this day of your slow-paced adventure in Italy.

After savoring a delicious meal, step into the vibrant nightlife at Caffè Fortebraccio, where the evening is just getting started. In the same way, Caffe Del Banco offers a unique charm perfect for experiencing the local bar scene in Perugia. Dempsey's Perugia is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 3 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Siena for 3 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Today, you'll explore some of the most beautiful places in Perugia, including a monument, a church, a palace, a public square and much more! Start your day with a visit to Fortezza Medicea (siena). This up-and-coming monument is a must-visit in the city. When you’re ready for your next discovery, continue to Battistero Di San Giovanni Battista, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Perugia 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 Siena Cathedral, a popular church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pubblico Palace and Piazza Del Campo. End your day with a visit to Tower Of Mangia, an underrated monument that’s sure to leave a lasting impression.

After a day of exploration, relax at one of the top hotels or accommodations in Siena. 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.

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.

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.

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

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 4 of your relaxed road trip across Italy, you’ll explore the area around Siena, where you’ll be staying for another 2 nights. 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.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming village of Siena. Your adventure starts at Piazza Del Duomo, an often recommended local hot spot. Another notable attraction to explore is Palazzo Comunale, Pinacoteca, Torre Grossa. This curiosity-inducing museum is known for its visually striking 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 Sangimignano1300. This photogenic museum offers a fascinating experience that many visitors find memorable.

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

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 Siena, explore the city like a local by trying out the best restaurants in the area.

Make sure to reserve a table at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

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

On day 5 of your relaxed road trip, you’ll start your self-paced adventure in Siena and visit amazing attractions in Greve in Chianti and Castellina in Chianti destinations, just outside of the city. You still have 1 night 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.

Savor the day by visiting some of the best places to see in Siena, including a castle and an archeological site. Start your adventure at Castle Of Verrazzano. This underrated castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Tumulo Di Montecalvario located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Rocca Di Castellina In Chianti. Its history-steeped features will captivate you.

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

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 delicious meal at Ristorante San Desiderio, a highly-rated dining destination in Siena. If you're eager to try something different, consider Osteria Le Logge, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

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

Day 6 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 Piazzale Michelangelo, a prime spot to begin your journey. This grand observation deck is sure to impress. Next on your list is Basilica Of Santa Croce In Florence, another must-visit landmark and notable church renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Uffizi Gallery. This romantic art gallery is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Ponte Vecchio, a timeless historical landmark. Nearby, you'll also find Palazzo Vecchio, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazza Della Signoria and wrap up your day with its grand appeal.

When you’re not exploring beautiful places, you’ll have a relaxed time at Florence. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze 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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Grab yourself a drink and savor every moment of your 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.

Set aside time today to explore Oltrarno, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Get ready to discover some of the most iconic wonders in Florence, including an art gallery, a food market, a church, a monument and much more! Start your day at Galleria Dell'accademia. This history-steeped art gallery is a notable place to see in Florence. Then, wander over to Central Market. If instagrammable sites excite you, this food market will be right up your alley. Nearby, you’ll also find Basilica Of San Lorenzo. This culturally significant church is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Cathedral Of Santa Maria Del Fiore is a spectacular spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the history-steeped Giotto's Bell Tower. Take a moment to appreciate the fascinating details of this up-and-coming monument.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

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.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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

Your laid-back and relaxed road trip in Italy continues on day 8, 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 Florence and beyond. With 1 night left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Today’s route brings fun adventures, breathtaking views, and photo-friendly spots. The first attraction of today is Leaning Tower Of Pisa. This wondrous monument is an UNESCO world heritage-listed place to see in Florence.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pisa Cathedral. This locally appreciated church offers a breathtaking encounter with Florence. Next, make your way to Campo Santo to add another highlight to your day. After that, visit Piazza Del Duomo, Pisa, a wondrous public square that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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

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

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.

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.

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