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.

Perugia is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and photo-friendly spots! Start at The Fontana Maggiore, a worthwhile monument that is worthwhile a visit in the city. Nearby, you’ll find Piazza Iv Novembre, enchanting visitors with its romantic appeal. Continue your exploration at National Archaeological Museum Of Umbria. This museum is one of the city’s most worthwhile spots.

Enjoy the freedom of exploring Perugia at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Basilica Of San Francesco D'assisi. After exploring the church, head to the often recommended Piazza Del Comune. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Basilica Di Santa Chiara, a place of breathtaking interest 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.

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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Caffè Fortebraccio, known for its inviting atmosphere. Caffe Del Banco is another great option if you’re looking for a place to get the night started. Similarly, Dempsey's Perugia provides a great setting to enjoy the night away.

Toast to another unforgettable and relaxing road trip adventure 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Perugia allows for both. Start by heading to Fortezza Medicea (siena). This often recommended monument provides an insightful glimpse into the city's identity. Next, discover Battistero Di San Giovanni Battista, a culturally significant church, promising a delightful encounter.

Continue your sightseeing with a visit to Siena Cathedral, an interesting church. When you’re done, don’t forget to make a stop at the frequently visited Pubblico Palace. Not far away from the palace, you will find the UNESCO world heritage-designated Tower Of Mangia, perfect for a quick visit. Round off your day at Piazza Del Campo, another gem in Perugia with history-steeped features to discover.

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.

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 delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Siena on today’s itinerary. First up is the frequently visited public square, Piazza Del Duomo. Afterward, continue to Palazzo Comunale, Pinacoteca, Torre Grossa, a museum every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Sangimignano1300. This curiosity-inducing museum is an essential stop.

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.

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena. If you're in the mood for something new, try Fischi per Fiaschi, another premier location with a delectable menu. You might also want to book a table at Osteria da Divo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

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.

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.

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

Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Siena. Begin your sightseeing with Castle Of Verrazzano. This underrated castle is one of the top attractions in the town. Proceed to Tumulo Di Montecalvario, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Rocca Di Castellina In Chianti. This beloved castle is a traveler-favorite.

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.

Enjoy a lovely meal at Ristorante San Desiderio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Le Logge is another top choice with a popular menu. You could also check for a table at Ristorante Taverna Di Cecco. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

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.

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

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This romantic observation deck is sure to ignite your curiosity. Next, dive into the culturally significant features of Basilica Of Santa Croce In Florence, a must-visit church 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 Uffizi Gallery, a widely recognized art gallery. For a change of scene, check out Ponte Vecchio, known for its romantic features. We also recommend visiting Palazzo Vecchio. This palace is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazza Della Signoria, yet another astonishing attraction in Siena.

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.

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.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

Day 7 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

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 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 heritage-rich art gallery is a popular 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 monumental 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 top-rated 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 enchanting Giotto's Bell Tower. Take a moment to appreciate the fascinating details of this frequently visited 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.

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.

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

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.

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

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.

Begin your adventure at Leaning Tower Of Pisa. This is a timeless monument you should not miss. Another must-see is Angelo Caduto, an up-and-coming point of interest in Florence.

When you’re ready for the next sight, head to Pisa Cathedral. From there, take a leisurely stroll to Campo Santo, another of the city’s worthwhile attractions. We recommend continuing your self-guided tour at Piazza Del Duomo, Pisa, a stunning place of interest in the city.

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.

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.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

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.