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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Sit back and enjoy a relaxed 8-day self-drive holiday in Italy. Along the way, Perugia, Santa Maria degli Angeli, Foligno, Siena, Florence, Pisa, Lucca, and Castellina in Chianti invite you to discover their unique blend of culture, scenery, and memorable experiences.

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 and soak in the atmosphere of the magnificent Leaning Tower Of Pisa.

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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Day1

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. Taking a stroll in the city center is a great alternative. 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 central location for easy access to key areas 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.

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

Extend your evening after a delightful meal by visiting Tommi Bar, which offers the perfect atmosphere for a night out. Moreover, Valentina is another popular option for a drink or two. Likewise, Caffe Dal Perugino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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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Day2

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

Your relaxed road trip in Italy continues on day 2 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Perugia and beyond. With 2 nights left in Perugia, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

No visit to Perugia is complete without Basilica Of Santa Maria Degli Angeli. This well-known church is one of the top attractions in the village. Proceed to Frontone Gardens, 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 Convent Of San Domenico. This often recommended church is a traveler-favorite. Not far away, you’ll find National Archaeological Museum Of Umbria, another key site on your sightseeing itinerary. Rocca Paolina is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Carducci Gardens and uncover why it's recognized as one of the village's most up-and-coming attractions.

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.

Dine in style at La Taverna, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante del Sole boasts a menu that's sure to impress. Also, be sure to check out Al Mangiar Bene. Known as a local hotspot, it’s a great choice for tonight in Perugia.

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

Extend your evening after a delightful meal by visiting Caffè Fortebraccio, which offers the perfect atmosphere for a night out. Moreover, Caffe Del Banco is another popular option for a drink or two. Likewise, Dempsey's Perugia 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.

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Day3

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 in Italy, you’ll start your self-paced adventure in Perugia and visit amazing attractions in Santa Maria degli Angeli and Foligno, just outside the city. You still have 1 night left in Perugia, so today is another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Enjoy all that Basilica Of San Francesco D'assisi has to offer. This is an interesting church you should not miss. Another must-see is Piazza Del Comune, a locally appreciated public square in Perugia.

When you’re ready for the next sight, head to Cathedral Of San Rufino. From there, take a leisurely stroll to Rocca Maggiore, another of the town’s intriguing attractions. We recommend continuing your self-guided tour at Porta Romana, a symbolic place of interest in the town.

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 wonderful meal at Perugia Plaza Hotel, a top-rated dining spot in Perugia. If you're in the mood for something new, try Elfo Pub Perugia, another premier location with a delectable menu. You might also want to book a table at Sangallo Palace Hotel. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Perugia.

As the day is coming to an end, stop at some of Perugia’s best bars to celebrate this day of your slow-paced adventure in Italy.

Keep the evening going at Il Birrino, a great choice for enjoying the after-dinner hours with a drink. You could also go to Quei Bravi Ragazzi, which offers a similarly pleasant setting and great drinks. Another option is Lo Chalet - Lounge Bar, which provides an inviting environment for unwinding after a busy day out.

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

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Day4

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

On day 4 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

Catch Pubblico Palace before the crowds roll in. This breathtaking palace is sure to ignite your curiosity. Next, dive into the breathtaking features of Tower Of Mangia, a must-visit monument 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 Piazza Del Campo, an astonishing public square. For a change of scene, check out Siena Cathedral, known for its inviting features. We also recommend visiting Fortezza Medicea (siena). This monument is a must for anyone looking to experience the city to the fullest.

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.

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 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 consistently gains 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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day5

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.

No visit to Florence is complete without Cathedral Of Santa Maria Del Fiore. This spectacular church is one of the top attractions in the city. Proceed to Palazzo Vecchio, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Ponte Vecchio. This timeless historical landmark is a traveler-favorite. Not far away, you’ll find Uffizi Gallery, another key site on your sightseeing itinerary. Basilica Of Santa Croce In Florence is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazzale Michelangelo and uncover why it's recognized as one of the city's most astonishing attractions.

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.

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.

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

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

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Day6

Day 6

  • Florence
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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.

Make a stop at Piazza Del Duomo, Pisa. This timeless public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Leaning Tower Of Pisa located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Dell'anfiteatro. Its enchanting features will captivate you. After the public square, continue your tour of the city with a visit to Guinigi Tower. Visitors usually appreciate the enchanting features of this monument. Next up is Mura Di Lucca, a highly recommended historical landmark.

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

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 Buca Mario, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Agricola Toscana is another top choice with a popular menu. You could also check for a table at Eataly Firenze. As an establishment that consistently gains high praises from customers, it’s an ideal choice 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 culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar 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 road trip adventure across Italy.

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Day7

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 self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Castellina in Chianti and end it in Perugia. You’ll stay in Perugia for 1 night. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Make time for Tumulo Di Montecalvario, an underrated archeological site that is worthwhile a visit in the village. Nearby, you’ll find Rocca Di Castellina In Chianti, enchanting visitors with its history-steeped appeal. Continue your exploration at Castello Di Brolio. This castle is one of the village’s most intriguing spots.

In Perugia, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

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.

Savor the flavors at Alphaville, a top pick for dinner tonight. Alternatively, Osteria a Priori beckons with its unique menu offerings. Also, consider La Bottega di Perugia. With its consistent customer satisfaction, it’s an excellent option for dining in Perugia tonight.

As the day is coming to an end, stop at some of Perugia’s best bars to celebrate this day of your slow-paced adventure in Italy.

Unwind after your meal by stepping into Punto Di Vista. This venue is celebrated for its extensive drink selections and cozy vibes.

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

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Day8

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’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.

Take advantage of your accommodation's proximity to Perugia’s shopping district for some last-minute bargain hunting. Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

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.

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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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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