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.

Today’s route brings fun adventures, scenic views, and photo-friendly spots. The first attraction of today is The Fontana Maggiore. This frequently visited monument is a picture-perfect place to see in Perugia. Continue your discovery at Piazza Iv Novembre, an enchanting public square with stories to tell.

As you stroll around Perugia, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to National Archaeological Museum Of Umbria. This underrated museum offers a respected encounter with Perugia. Next, make your way to Basilica Of San Francesco D'assisi to add another highlight to your day. After that, visit Piazza Del Comune, a beloved public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Basilica Di Santa Chiara, a curiosity-inducing church in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Perugia.

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.

Savor the flavors at La Taverna, a top pick for dinner tonight. Alternatively, Ristorante del Sole beckons with its unique menu offerings. Also, consider Al Mangiar Bene. With its consistent customer satisfaction, it’s an excellent option for dining in Perugia 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.

After your meal, keep the night alive at a bar like Caffè Fortebraccio, known for its lively atmosphere. Caffe Del Banco is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Dempsey's Perugia 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 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!

A blend of fun adventures, breathtaking views, and picturesque spots await you in Perugia on today’s itinerary. First up is the underrated 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 interesting 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 famous public square in the city. Finally, end your day with a visit to Tower Of Mangia, a breathtaking monument that offers the perfect conclusion to your sightseeing of the day.

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

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 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.

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

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most intriguing attractions included on the itinerary is Piazza Del Duomo. This UNESCO world heritage-listed public square will help you start your sightseeing on top. Then, take a leisurely stroll to Palazzo Comunale, Pinacoteca, Torre Grossa and learn what makes this breathtaking museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile Sangimignano1300.

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.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start. You could also check out Bar Pinacoteca, offering a different kind of charm. A last recommendation for the day is San Paolo Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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 locally appreciated places to visit in Siena. Next, head to Tumulo Di Montecalvario, a beloved archeological site, known for its photogenic 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 romantic 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.

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 Ristorante San Desiderio, a top-rated dining spot in Siena. If you're in the mood for something new, try Osteria Le Logge, another premier location with a delectable menu. You might also want to book a table at Ristorante Taverna Di Cecco. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

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

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

On day 6 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.

Today, you'll explore some of the most beautiful places in Siena, including an observation deck, a church, an art gallery, a historical landmark, a palace, a public square and much more! Start your day with a visit to Piazzale Michelangelo. This famous observation deck is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of Santa Croce In Florence, which may be one of the most standout 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 Uffizi Gallery, an astonishing art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Ponte Vecchio and Palazzo Vecchio. End your day with a visit to Piazza Della Signoria, an extraordinary public square that’s sure to leave a lasting impression.

In the city of Florence, 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, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

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

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

Cherish every minute of your relaxed road trip vacation across 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.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes an art gallery, a food market, a church, a monument and much more! Begin your adventure at Galleria Dell'accademia. This is a well-known art gallery you should not miss. Another must-see is Central Market, a locally renowned food market in Florence.

When you’re ready for the next sight, head to Basilica Of San Lorenzo. From there, take a leisurely stroll to Cathedral Of Santa Maria Del Fiore, another of the city’s extraordinary attractions. We recommend continuing your self-guided tour at Giotto's Bell Tower, a visually striking place of interest in the city.

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.

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.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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.

Set out on a day brimming with family-friendly attractions, scenic views, and photo-friendly spots. Start at the iconic Leaning Tower Of Pisa, a remarkable 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 breathtaking 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 majestic places to visit in Florence.

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

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.

Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!