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

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Photo of Christmas in Assisi, Saint Francis Basilica with the Christmas Crib. Province of Perugia, Umbria, Italy.
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Enjoy this 8-day relaxed road trip in Italy, with Perugia, Santa Maria degli Angeli, Foligno, Siena, Florence, Pisa, Lucca, and Castellina in Chianti showing you the beauty, culture, and peaceful moments that make this journey special!

Travel freely with this relaxed self-drive package in Italy, designed for comfort and exploration. Spend 4 nights in Perugia and 3 nights in Florence, staying at top-rated hotels near the heart of each city. Between drives, indulge in local cuisine, sip refreshing drinks, and enjoy the vibrant atmosphere at popular restaurants and bars along your road trip route in Italy.

Your journey starts in Perugia, where your rental car with CDW insurance will be ready for pickup. Choose a vehicle that suits your style, then set off on your 8-day relaxed road trip in Italy to explore its rich culture, fascinating history, and stunning landscapes.

Every stop on this leisurely self-drive holiday comes with handpicked accommodations that make relaxation effortless. Choose from elegant 5-star hotels with breathtaking views or comfortable 3-star stays that offer excellent value, all providing a welcoming retreat after a day on the road.

With your self-drive itinerary in Italy already planned, you’ll enjoy the country’s most celebrated sights without the rush. Marvel at the stunning Ponte Vecchio, wander through the remarkable Piazza Del Duomo, Pisa, and soak in the atmosphere of the magnificent Leaning Tower Of Pisa.

Continue your journey with a visit to the iconic Piazzale Michelangelo, a highlight that captures the spirit of the destination. Visit the spectacular Cathedral Of Santa Maria Del Fiore and Piazza Del Campo. Enjoy each stop as you explore the history, architecture, and character of each destination on this Italy road trip itinerary for 8 days.

As you travel between destinations, you’ll have plenty of time to explore local markets and boutique shops. These stops give you the chance to find unique souvenirs, taste regional specialties, and experience everyday life in Italy.

If you want to make your 8-day relaxed self-drive tour in Italy even more memorable, add optional tours or activities. Join a guided excursion, discover hidden neighborhoods, or spend an afternoon in your favorite market. Each choice deepens your connection to the places you visit.

Alongside these experiences, your laid-back self-drive package in Italy includes 7 nights in comfortable hotels, a rental car for 8 days, and convenient access to nearby dining options. You can also add flights and entry tickets to shape the trip exactly how you want it. With 24/7 travel support and a mobile app keeping your itinerary and documents organized, you can enjoy a relaxed drive and savor every mile of the road ahead.

Turn your travel plans into reality. Book your 8-day relaxed self-drive road trip in Italy today and enjoy a journey filled with discovery, freedom, and unforgettable moments!

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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.

Find your way to your hotel in Perugia. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Enjoy a delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

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

Continue your lively evening at Tommi Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Valentina is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffe Dal Perugino ensures a night out tailored to your taste.

Raise a toast as you look back on the highlights of today’s relaxed road trip 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 in Italy, you’ll start your self-paced adventure in Perugia and visit amazing attractions in Santa Maria degli Angeli and Perugia, just outside the city. You still have 2 nights left in Perugia, so today is another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Your adventure in Perugia is only getting started when you visit Basilica Of Santa Maria Degli Angeli, a well-known local hot spot. Another notable attraction to explore is Frontone Gardens. This often recommended park is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Perugia's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Convent Of San Domenico. This photogenic church offers a fascinating experience that many visitors find memorable. National Archaeological Museum Of Umbria is also worth visiting, along with Rocca Paolina. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Carducci Gardens. This curiosity-inducing park provides a fitting finale to your sightseeing.

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

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 delicious dinner at La Taverna, an excellent option for tonight's dining. Looking for something different? Ristorante del Sole offers a tantalizing alternative with its diverse menu. And don’t miss Al Mangiar Bene. Known for great service, it’s a fantastic choice for tonight in Perugia.

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

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.

A leisurely self-drive holiday in Santa Maria degli Angeli can’t get any better than this! Toast to another amazing day 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

Your relaxed road trip in Italy continues on day 3 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Perugia and beyond. With 1 night left in Perugia, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

Basilica Of San Francesco D'assisi is perfect for a self-paced visit during the day. This UNESCO world heritage-designated church is sure to impress. Next on your list is Piazza Del Comune, another must-visit landmark and locally appreciated public square renowned for its romantic features.

While exploring and sightseeing, take time to savor the culture of Perugia by sampling some local delicacies. When you’re ready for more sightseeing, head to Cathedral Of San Rufino. This historic church is an essential place to visit for anyone looking for the full Perugia experience. We also recommend visiting Rocca Maggiore, an up-and-coming castle. Nearby, you'll also find Porta Romana, ready to add charm to your journey.

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

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.

Explore the vibrant nightlife at Il Birrino after your meal, a hub for lively evenings and memorable moments. Or, head to Quei Bravi Ragazzi for a great selection of flavorful drinks and a charming setting. Furthermore, Lo Chalet - Lounge Bar is perfect for those looking to extend their night with a touch of local flavor.

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 4

Day 4

  • Perugia
  • Florence
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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 offers a chance to experience the country’s diversity. You’ll start your day in Siena and end it in Florence. You’ll stay in Florence for 3 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Start your day at Pubblico Palace. This awe-inspiring palace is an underrated place to see in Perugia. Then, wander over to Tower Of Mangia. If UNESCO world heritage-designated sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Del Campo. This history-steeped public square 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, Siena Cathedral is a captivating 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 picture-perfect Fortezza Medicea (siena). Take a moment to appreciate the fascinating details of this underrated monument.

When you’re not exploring beautiful places, you can relax in Florence. Here, you can choose from the best hotels and other accommodations as you get to know more about the culture in the city.

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 delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass and relax after another big day of your leisurely paced road trip in 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 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Look forward to a unique sightseeing adventure at the widely recognized Cathedral Of Santa Maria Del Fiore and allow yourself time to explore. Just a short distance away you'll find your next stop, Palazzo Vecchio, a visually striking palace that draws visitors from far and near.

Continue your journey to Ponte Vecchio, one of the city’s most globally renowned spots that you shouldn’t miss. Another great site to visit is the famous Uffizi Gallery. When you're finished at the art gallery, Basilica Of Santa Croce In Florence awaits your visit. This church is a photogenic highlight on today's itinerary. Last up is an observation deck - the impressive Piazzale Michelangelo.

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.

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.

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.

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

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Cherish every minute of your relaxed road trip vacation 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

On day 6 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.

Whatever your travel style is, Piazza Del Duomo, Pisa is an essential stop in Florence. This globally renowned public square provides an insightful glimpse into the city's identity. Next, discover Leaning Tower Of Pisa, a breathtaking monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Dell'anfiteatro, a locally renowned public square. When you’re done, don’t forget to make a stop at the increasingly popular Guinigi Tower. Round off your day at Mura Di Lucca, another gem in Florence with history-steeped features to discover.

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

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.

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

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.

Continue the enjoyment post-dinner at Gosh*, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Antico Caffè Del Moro - Art Bar Firenze offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Quelo Bar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Experience Tumulo Di Montecalvario, a worthwhile archeological site in the village. Then, head to Rocca Di Castellina In Chianti and soak in the ambiance of this romantic castle.

There are many interesting places to see in Florence, and when you are ready for more, go to Castello Di Brolio. This is one of the village’s most underrated awe-inspiring spots of interest.

You'll be staying in Perugia on this laid-back road trip through Italy. You'll stay here for 1 night.

Exploring new places makes you hungry. Luckily, Perugia 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 Alphaville, 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 Osteria a Priori, 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 La Bottega di Perugia, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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 evening by exploring the vibrant nightlife scene at Punto Di Vista, a prime destination for a thrilling 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 8

Day 8

  • Perugia - Departure day
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  • Piazza IV Novembre
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Day 8 of your relaxed road trip in Italy is your departure day. If you’re flying home, return your rental car with time to spare. For a stress-free farewell, book a later flight and enjoy a final, relaxed day in Perugia.

If you're up for some more sightseeing, begin at Piazza Iv Novembre. This frequently visited public square is a hotspot among locals.

Over a good meal, take a moment to unwind and reflect on the past 8 days of your relaxed road trip. Savor one last traditional dish in Perugia, or keep it light with a quick bite before you go.

If you're in the mood for something new, try Locanda Del Bartoccio, another premier location with a delectable menu.

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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Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
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Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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