One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Perugia to Florence

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Uncover the beauty of Italy on this 8-day relaxed road trip, journeying through Perugia, Santa Maria degli Angeli, Foligno, Siena, Florence, Pisa, Lucca, and Castellina in Chianti. Unwind at your leisure on this self-drive vacation, discovering hidden gems and immersing yourself in the serene exploration.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Perugia, Santa Maria degli Angeli, Foligno, Siena, Florence, Pisa, Lucca, and Castellina in Chianti. Make yourself at home at top-rated hotels and stay 4 nights in Perugia and 3 nights in Florence. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.

Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Perugia, you’ll collect your rental car of choice. From there, you’ll begin your 8-day journey across Italy and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.

We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Ponte Vecchio. Another highlight of this self-drive tour is the captivating Leaning Tower Of Pisa.

Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Piazza Del Duomo, Pisa. With this travel plan, you could also soak in the atmosphere of the memorable Piazzale Michelangelo. Get close to the spectacular Cathedral Of Santa Maria Del Fiore and the wonderful Piazza Del Campo. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.

Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 7 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 8 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 8-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Italy today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Etruscan Arch
Basilica of Santa Maria degli AngeliFrontone GardensConvent of San DomenicoNational Archaeological Museum of UmbriaRocca PaolinaCarducci Gardens
Basilica of San Francesco d'AssisiPiazza del ComuneCathedral of San RufinoRocca MaggiorePorta Romana
Pubblico PalaceTower of Mangiapiazza del CampoSiena CathedralFortezza Medicea
Cathedral of Santa Maria del FiorePalazzo VecchioPonte VecchioUffizi GalleryBasilica of Santa Croce in Florencepiazzale Michelangelo
Piazza del Duomo, PisaLeaning Tower of PisaPiazza dell'AnfiteatroGuinigi TowerWalls of Lucca
Tumulo di MontecalvarioRocca di Castellina in ChiantiCastello di Brolio
Piazza IV Novembre

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Day 1

Day 1

  • Perugia - Arrival day
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  • Etruscan Arch
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Your relaxed road trip through Italy starts when you reach the incredible city of Perugia, where you'll stay for 3 nights. You'll pick up your rental car in Perugia and begin your adventure in Italy.

Perugia is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Etruscan Arch, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Perugia. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Perugia, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Ristorante Settimo Sigillo, 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 Caffè Baglioni, 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 Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Continue your evening by exploring the vibrant nightlife scene at Tommi Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Valentina, a bar that offers unique local touches. Likewise, Caffe Dal Perugino provides an excellent alternative for a fun evening.

Raise a toast as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Perugia as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Perugia
  • More

Drive 44 km, 1 hour 14 min

  • Basilica of Santa Maria degli Angeli
  • Frontone Gardens
  • Convent of San Domenico
  • National Archaeological Museum of Umbria
  • Rocca Paolina
  • Carducci Gardens
  • More

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

Today’s agenda in Perugia includes a church, a park, a museum, a historical landmark and much more! Basilica Of Santa Maria Degli Angeli is must-visit church and a great starting point for the day. Next, continue your journey to Frontone Gardens, a frequently visited park, located just a leisurely stroll away. Next, head to Convent Of San Domenico, a culturally significant church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Perugia. When you're ready, let your sightseeing route take you to the intriguing National Archaeological Museum Of Umbria. If you’re looking for more, Rocca Paolina is also a beloved attraction that is worthwhile a visit. Lastly, don’t miss Carducci Gardens, a place of romantic interest in the village.

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.

Treat yourself to a wonderful meal at La Taverna, a top-rated dining spot in Perugia. If you're in the mood for something new, try Ristorante del Sole, another premier location with a delectable menu. You might also want to book a table at Al Mangiar Bene. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Perugia.

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

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.

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

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Day 3

Day 3

  • Perugia
  • More

Drive 84 km, 2 hours 4 min

  • Basilica of San Francesco d'Assisi
  • Piazza del Comune
  • Cathedral of San Rufino
  • Rocca Maggiore
  • Porta Romana
  • More

On day 3 of your relaxed road trip, you’ll start your self-paced adventure in Perugia and visit amazing attractions in Santa Maria degli Angeli and Foligno 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.

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Perugia. Begin your sightseeing with Basilica Of San Francesco D'assisi. This well-known church is one of the top attractions in the town. Proceed to Piazza Del Comune, another must-visit attraction.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Cathedral Of San Rufino. This beloved church is a traveler-favorite. Not far away, you’ll find Rocca Maggiore, another key site on your sightseeing itinerary. Porta Romana is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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

Make sure to reserve a table at Perugia Plaza Hotel, 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 Elfo Pub Perugia, 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 Sangallo Palace Hotel, 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.

Round off your dining experience by visiting Il Birrino, a prime location for a drink. Alternatively, explore the distinctive characteristics of Quei Bravi Ragazzi, a bar catering to every mood and preference. Lo Chalet - Lounge Bar likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 4

Day 4

  • Perugia
  • Florence
  • More

Drive 180 km, 3 hours 4 min

  • Pubblico Palace
  • Tower of Mangia
  • piazza del Campo
  • Siena Cathedral
  • Fortezza Medicea
  • More

Day 4 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Florence 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.

Enjoy the perfect balance of relaxation and exploration in Perugia today. One of the most underrated attractions included on the itinerary is Pubblico Palace. This picture-perfect palace will help you start your sightseeing on top. Then, take a leisurely stroll to Tower Of Mangia and learn what makes this UNESCO world heritage-listed monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the extraordinary Piazza Del Campo. After exploring the public square, head to Siena Cathedral. This captivating church is a highlight in Perugia. As your day continues, stop by Fortezza Medicea (siena), known for its breathtaking features.

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 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.

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 Florence. The bars in Florence make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

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

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Day 5

Day 5

  • Florence
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Drive 8 km, 1 hour 3 min

  • Cathedral of Santa Maria del Fiore
  • Palazzo Vecchio
  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

Day 5 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!

Start by visiting Cathedral Of Santa Maria Del Fiore, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Palazzo Vecchio, another must-visit landmark and captivating palace renowned for its symbolic features.

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 Ponte Vecchio. This visually striking historical landmark is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Uffizi Gallery, a widely recognized art gallery. Nearby, you'll also find Basilica Of Santa Croce In Florence, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazzale Michelangelo and wrap up your day with its enchanting appeal.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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 excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 6

Day 6

  • Florence
  • More

Drive 196 km, 3 hours 17 min

  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Piazza dell'Anfiteatro
  • Guinigi Tower
  • Walls of Lucca
  • More

Your laid-back and relaxed road trip in Italy continues on day 6, 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.

Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo, Pisa. This iconic public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Leaning Tower Of Pisa, one of the city’s best highlights.

Next, check out Piazza Dell'anfiteatro, one of the most interesting places to see in Florence. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Guinigi Tower. Wander around and soak in the visually striking atmosphere this monument offers. Then, head to Mura Di Lucca, a top-rated historical landmark that adds another dimension to your day.

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

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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence 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.

After savoring a delicious meal, step into the vibrant nightlife at Gosh*, where the evening is just getting started. In the same way, Antico Caffè Del Moro - Art Bar Firenze offers a unique charm perfect for experiencing the local bar scene in Florence. Quelo Bar 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 Pisa can’t get any better than this! Toast to another amazing day in Italy!

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Day 7

Day 7

  • Florence
  • Perugia
  • More

Drive 183 km, 3 hours 11 min

  • Tumulo di Montecalvario
  • Rocca di Castellina in Chianti
  • Castello di Brolio
  • More

Day 7 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. On this refreshing new day, you’ll travel from Castellina in Chianti and continue your laid-back and relaxed road trip adventure in the hamlet of San Regolo and the city of Perugia. You’ll stay in Perugia for 1 night.

Today’s route brings fun adventures, photo-friendly spots, and historic treasures. The first attraction of today is Tumulo Di Montecalvario. This beloved archeological site is a symbolic place to see in Florence. Continue your discovery at Rocca Di Castellina In Chianti, an enchanting castle with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Castello Di Brolio. This frequently visited castle offers an enchanting encounter with Florence. 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 not exploring beautiful places, you’ll have a relaxed time at Perugia. 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 Perugia, explore the city like a local by trying out the best restaurants in the area.

Enjoy a lovely dining experience at Alphaville, a popular restaurant in Perugia. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Perugia at Osteria a Priori, 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 La Bottega di Perugia. It’s yet another ideal choice to enhance your time in Perugia tonight.

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

Keep the evening going at Punto Di Vista, a great choice for enjoying the after-dinner hours with a drink.

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.

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Day 8

Day 8

  • Perugia - Departure day
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  • Piazza IV Novembre
  • More

Day 8 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Perugia.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Perugia's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

If you're up for some more sightseeing, begin at Piazza Iv Novembre. This intriguing public square is a popular place to see in the city.

Unwind and look back at the past 8 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Perugia or just grab something light to keep you going.

Dine in style at Ristorante IL CANTINONE Perugia, a top recommendation for dinner tonight. Or, for a change of pace, Locanda Del Bartoccio boasts a menu that's sure to impress.

Give yourself enough time to wave goodbye to Perugia and begin your journey home. The unforgettable experiences you’ve collected along your 8-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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