9-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena and Florence

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Experience the freedom of the open road in Italy as you embark on an unforgettable 9-day road trip! This experience caters to every traveler, featuring destinations like Perugia, Santa Maria degli Angeli, Spello, Siena, Florence, Pisa, Lucca, and Orvieto.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 4 nights in Perugia, 1 night in Siena, and 3 nights in Florence. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Perugia, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Ponte Vecchio and Leaning Tower Of Pisa are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Del Duomo, Pisa, learn more about the unique Piazzale Michelangelo, and immerse yourself in the vibrant atmosphere of Cathedral Of Santa Maria Del Fiore.

As you hit the open road and drive through Perugia, Santa Maria degli Angeli, Spello, Siena, Florence, Pisa, Lucca, and Orvieto, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Rocca Paolina
Etruscan ArchPerugia CathedralPiazza IV NovembreNational Archaeological Museum of UmbriaConvent of San DomenicoFrontone Gardens
Basilica of San Francesco d'AssisiPiazza del ComuneBasilica di Santa ChiaraRocca MaggioreMount SubasioPorta Consolare
Fortezza MediceaBasilica of San DomenicoSiena CathedralPubblico Palacepiazza del CampoTower of Mangia
piazzale MichelangeloBargello National MuseumBasilica of Santa Croce in FlorenceUffizi GalleryPonte Vecchiopiazza della Signoria
Palazzo PittiCathedral of Santa Maria del FioreGalleria dell'AccademiaCentral MarketBasilica of Santa Maria NovellaOltrarno

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Day 1

Day 1

  • Perugia - Arrival day
  • More
  • Rocca Paolina
  • More

Your road trip adventure in Italy begins as soon as you reach Perugia and pick up your car. You’ll stay in Perugia for 3 nights and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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 Rocca Paolina, 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.

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 to the start of your 9-day road trip in Italy!

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Day 2

Day 2

  • Perugia
  • More

Drive 4 km, 40 min

  • Etruscan Arch
  • Perugia Cathedral
  • Piazza IV Novembre
  • National Archaeological Museum of Umbria
  • Convent of San Domenico
  • Frontone Gardens
  • More

Day 2 of your road trip across Italy promises a magnificent time exploring Perugia. You have 2 nights left in Perugia. Take the opportunity to experience more of the best attractions and activities in the city.

Today, you'll explore some of the most beautiful places in Perugia, including a historical landmark, a church, a public square, a museum, a park and much more! Start your day with a visit to Etruscan Arch. This frequently visited historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Perugia Cathedral, which may be one of the most instagrammable places you will experience today.

One of the best things about exploring Perugia 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 Piazza Iv Novembre, an up-and-coming public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for National Archaeological Museum Of Umbria and Convent Of San Domenico. End your day with a visit to Frontone Gardens, an increasingly popular park that’s sure to leave a lasting impression.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Enjoy a delicious meal at La Taverna, a highly-rated dining destination in Perugia. If you're eager to try something different, consider Ristorante del Sole, another top spot with a tantalizing menu. You might also want to secure a reservation at Al Mangiar Bene. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Perugia this evening.

Keep the excitement of the evening going by visiting a bar or two. Caffè Fortebraccio is an excellent place to start. You could also check out Caffe Del Banco, offering a different kind of charm. A last recommendation for the day is Dempsey's Perugia. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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Day 3

Day 3

  • Perugia
  • More

Drive 77 km, 2 hours 4 min

  • Basilica of San Francesco d'Assisi
  • Piazza del Comune
  • Basilica di Santa Chiara
  • Rocca Maggiore
  • Mount Subasio
  • Porta Consolare
  • More

At the end of the day, you'll drive back to Perugia, where you'll stay for 1 night more.

Brace yourself for today’s incredible lineup of attractions in Perugia, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Basilica Of San Francesco D'assisi, an interesting church in the town. Then, head to Piazza Del Comune and soak in the ambiance of this symbolic public square.

There are many interesting places to see in Perugia and when you are ready for more, go to Basilica Di Santa Chiara. This is one of the town’s most up-and-coming spots. After exploring the church, visit the intriguing Rocca Maggiore. Before wrapping up your self-guided sightseeing tour, head to the often recommended Mount Subasio, an often recommended mountain range in the town.

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

As you explore more of Perugia, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Treat yourself to a delightful dinner at Perugia Plaza Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Elfo Pub Perugia? It's another excellent option with a diverse menu. Consider reserving a table at Sangallo Palace Hotel as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Il Birrino, a well-loved spot among locals and tourists. Or, head to Quei Bravi Ragazzi. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Lo Chalet - Lounge Bar, another top-rated place in the area.

Get a good night's sleep and look forward to another great day on the road in Italy!

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Day 4

Day 4

  • Perugia
  • Siena
  • More

Drive 110 km, 1 hour 59 min

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the locally appreciated Fortezza Medicea (siena), a breathtaking monument in Perugia. Next, go to Basilica Of San Domenico.

After visiting Fortezza Medicea (siena) and Basilica Of San Domenico, take time to explore Perugia's streets and absorb its charm. Continue your sightseeing by heading to Siena Cathedral. This grand church offers a unique experience. Pubblico Palace is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Piazza Del Campo, one of the most enchanting places to visit in Perugia.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 5

Day 5

  • Siena
  • Florence
  • More

Drive 75 km, 1 hour 51 min

  • piazzale Michelangelo
  • Bargello National Museum
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • piazza della Signoria
  • More

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 3 nights.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This enchanting observation deck is sure to ignite your curiosity. Next, dive into the eye-catching features of Bargello National Museum, a must-visit museum 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 Basilica Of Santa Croce In Florence, an interesting church. For a change of scene, check out Uffizi Gallery, known for its historic features.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

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

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 6

Day 6

  • Florence
  • More

Drive 4 km, 1 hour 3 min

  • Palazzo Pitti
  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • Central Market
  • Basilica of Santa Maria Novella
  • Oltrarno
  • More

Day 6 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

One of the most iconic places you can visit today in Florence is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await. Pitti Palace is the perfect place to start. This palace is one of the most locally renowned places to visit in Florence. Next, head to Cathedral Of Santa Maria Del Fiore, an extraordinary church, known for its visually striking 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 Galleria Dell'accademia. This history-steeped art gallery offers a unique experience that is highly recommended. Meanwhile, Central Market adds its own distinct charm to your journey. Finish your day with a visit to Basilica Di Santa Maria Novella, Firenze (fi), a culturally significant church in Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

Say good night to Florence and look forward to another great day of your road trip in Italy!

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Day 7

Day 7

  • Florence
  • More

Drive 196 km, 3 hours 13 min

  • Battistero di San Giovanni
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Guinigi Tower
  • San Michele in Foro
  • Walls of Lucca
  • More

Wake up to day 7 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a monument, a historical landmark and much more! Start your adventure at Battistero Di San Giovanni. This up-and-coming church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Piazza Del Duomo, Pisa, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Leaning Tower Of Pisa. This timeless monument offers an enriching experience. For a change of pace, head to Guinigi Tower, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to San Michele In Foro and San Michele In Foro. These sights offer a fulfilling end to a perfect day.

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

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

Enjoy a delicious meal 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.

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.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 8

Day 8

  • Florence
  • Perugia
  • More

Drive 242 km, 3 hours 46 min

  • Well of St Patrick
  • Orvieto Cathedral
  • Museo dell'Opera del Duomo
  • Orvieto subterranea
  • Torre del Moro Orvieto
  • Pozzo della Cava
  • More

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Florence. Some of the village’s most loved attractions await. Well Of St. Patrick is the perfect place to start. This monument is one of the most popular places to visit in Florence. Next, head to Orvieto Cathedral, a well-known church, known for its romantic 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 Museo Dell'opera Del Duomo. This noteworthy museum offers a unique experience that is highly recommended. Meanwhile, Orvieto Underground adds its own distinct charm to your journey. Finish your day with a visit to Torre Del Moro Orvieto, a picture-perfect monument in Florence.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Perugia. Perugia offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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.

Keep the excitement of the evening going by visiting a bar or two. Punto Di Vista is an excellent place to start.

Raise your glass to another unforgettable day in Italy!

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Day 9

Day 9

  • Perugia - Departure day
  • More
  • Saint Pietro Gate
  • More

Day 9 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Perugia before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, we recommend visiting Saint Pietro Gate, a culturally significant monument before you head out.

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.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Perugia.

If you're in the mood to try something new, consider Locanda Del Bartoccio, another top spot with a mouthwatering menu.

You’ll then say farewell to Perugia. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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