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.

Get ready to discover some of the most iconic wonders in Perugia, including a monument, a public square, a museum, a church and much more! Start your day at The Fontana Maggiore. This picture-perfect monument is an intriguing place to see in Perugia. Then, wander over to Piazza Iv Novembre. If romantic sites excite you, this public square will be right up your alley. Nearby, you’ll also find National Archaeological Museum Of Umbria. This instagrammable museum is a favorite among visitors.

Perugia offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Basilica Of San Francesco D'assisi is a notable 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 romantic Piazza Del Comune. Take a moment to appreciate the fascinating details of this locally appreciated public square. Wrap up your self-guided tour of Perugia's top attractions with a visit to Basilica Di Santa Chiara.

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

After dinner, it’s time to fall in love with the amazing nightlife in Perugia and unwind at some of the best bars in the city.

Continue your lively evening at Caffè Fortebraccio, a perfect place for winding down or revving up the night, depending on which mood you’re in. Caffe Del Banco is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Dempsey's Perugia ensures a night out tailored to your taste.

Soak in the unique atmosphere of Perugia as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday in Italy!

On day 3 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

A blend of family-friendly attractions, breathtaking views, and photo-friendly spots await you in Perugia on today’s itinerary. First up is the often recommended monument, Fortezza Medicea (siena). Afterward, continue to Battistero Di San Giovanni Battista, a church every traveler should visit.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Siena Cathedral. This well-known church is an essential stop. Following that, head to Pubblico Palace, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Campo, a spectacular public square in the city. Finally, end your day with a visit to Tower Of Mangia, an awe-inspiring monument that offers the perfect conclusion to your sightseeing of the day.

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

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.

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.

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.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Soak in the unique atmosphere of Siena as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday 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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, romantic experiences, and breathtaking views. Start at Piazza Del Duomo, a locally appreciated public square in the village. Then, head to Palazzo Comunale, Pinacoteca, Torre Grossa and soak in the ambiance of this UNESCO world heritage-designated museum.

There are many interesting places to see in Siena, and when you are ready for more, go to Sangimignano1300. This is one of the village’s most underrated visually striking spots of interest.

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.

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Fischi per Fiaschi? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

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

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.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

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.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a castle and an archeological site. Begin your adventure at Castle Of Verrazzano. This is an underrated castle you should not miss. Another must-see is Tumulo Di Montecalvario, an intriguing archeological site in Siena.

When you’re ready for the next sight, head to Rocca Di Castellina In Chianti.

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

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 lovely dining experience at Ristorante San Desiderio, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Osteria Le Logge, 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 Ristorante Taverna Di Cecco. It’s yet another ideal choice to enhance your time in Siena tonight.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Siena.

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

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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, romantic experiences, and breathtaking views. Start at Piazzale Michelangelo, an astonishing observation deck in the city. Then, head to Basilica Of Santa Croce In Florence and soak in the ambiance of this photogenic church.

There are many interesting places to see in Siena, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most impressive romantic spots of interest. After exploring the art gallery, visit the iconic Ponte Vecchio. Not far away, you'll also find Palazzo Vecchio. This palace is a symbolic highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Piazza Della Signoria, a famous public square in the city.

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.

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 Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 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 detailed art gallery is a locally renowned place to see in Florence. Then, wander over to Central Market. If eye-catching sites excite you, this food market will be right up your alley. Nearby, you’ll also find Basilica Of San Lorenzo. This photogenic 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 an impressive 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 intriguing monument.

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.

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 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.

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

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Cherish every minute of your relaxed road trip vacation across 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.

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the globally renowned Leaning Tower Of Pisa, a picture-perfect monument in Florence. Next, go to Angelo Caduto.

After visiting Leaning Tower Of Pisa and Angelo Caduto, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Pisa Cathedral. This culturally significant church offers a unique experience. Campo Santo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Del Duomo, Pisa, one of the most picture-perfect places to visit in Florence.

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

Exploring the food culture in Florence 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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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.

Keep the evening going at Gosh*, a great choice for enjoying the after-dinner hours with a drink. You could also go to Antico Caffè Del Moro - Art Bar Firenze, which offers a similarly pleasant setting and great drinks. Another option is Quelo Bar, which provides an inviting environment for unwinding after a busy day out.

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