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

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Porta di Venere, from the Roman era, made of white travertine, with its three arches and the two towers of Properzio in Perugia, Italy
Photo of Christmas in Assisi, Saint Francis Basilica with the Christmas Crib. Province of Perugia, Umbria, Italy.
9-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena and Florence
9-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena and Florence
9-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena and Florence
9-Day Italy Self-Drive Road Trip With Itinerary from Perugia to Siena and Florence
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 on an unforgettable 9-day road trip in Italy! Embark on a self-drive tour that 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 takes you through some of the best places to see in Italy. 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 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.

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, accommodations, 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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Driver’s age is 30 - 65
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Day1

Day 1

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

Welcome to Perugia, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 3 nights discovering what to see in Perugia before embarking on the next leg of your journey.

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. 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.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Perugia. Make yourself at home and unwind before heading out again.

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.

Have a fantastic dining experience at Ristorante Settimo Sigillo, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffè Baglioni offers an enticing alternative with its varied menu. Additionally, Bar Pellas is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Perugia.

After savoring a delicious meal, step into the vibrant nightlife at Tommi Bar, where the evening is just getting started. In the same way, Valentina offers a unique charm perfect for experiencing the local bar scene in Perugia. Caffe Dal Perugino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day2

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

On day 2 of your road trip, you will have an entire day to discover what to see in Perugia. You’ll stay in Perugia for 2 nights.

To truly experience Perugia, make sure to drop by Etruscan Arch. This locally appreciated historical landmark is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Perugia Cathedral, one of the city’s best highlights.

Next, check out Piazza Iv Novembre, one of the most locally appreciated places to see in Perugia. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, National Archaeological Museum Of Umbria. Wander around and soak in the standout atmosphere this museum offers. Then, head to Convent Of San Domenico, a top-rated church that adds another dimension to your day. Finally, visit the beloved Frontone Gardens, the last of our attraction recommendations for today.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

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.

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.

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

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Day3

Day 3

  • Perugia
  • Assisi
  • Spello
  • 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

Wake up to day 3 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Santa Maria degli Angeli and Spello. With 1 night to stay in Perugia, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Whether you decide to explore Santa Maria degli Angeli on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Santa Maria degli Angeli. This drive usually takes around 32 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Basilica Of San Francesco D'assisi, a well-known church in Santa Maria degli Angeli. Explore its breathtaking features at your own pace before you continue your journey to your next attraction, Piazza Del Comune. This intriguing public square is a top recommendation in the area.

When you’re ready to explore more, Basilica Di Santa Chiara is an excellent choice. Spend some time discovering what some claim to be the most culturally significant church in the region. Next, continue your sightseeing at the often recommended Rocca Maggiore and discover what makes this castle unique. If you’re up for one more stop in the town, head to Mount Subasio, a serene mountain range many travelers find the visit worthwhile.

When you’re ready to jump back into the car and say goodbye to Santa Maria degli Angeli, you’ll hit the road in the direction of Spello. This drive usually takes around 22 min.

Our first attraction recommendation in Spello is Porta Consolare, a curiosity-inducing monument that draws attention for its photogenic features.

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

Perugia is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Perugia.

Dine in style at Perugia Plaza Hotel, a top recommendation for dinner tonight. Or, for a change of pace, Elfo Pub Perugia boasts a menu that's sure to impress. Also, be sure to check out Sangallo Palace Hotel. Known as a local hotspot, it’s a great choice for tonight in Perugia.

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.

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

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Day4

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Siena. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

After soaking in Perugia’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 25 min. When you arrive in Siena, it's time to take a break from the road.

Our first attraction recommendation in Siena is Fortezza Medicea (siena), a beloved monument that draws attention for its picture-perfect features. Spend some time soaking in the atmosphere before continuing to Basilica Of San Domenico, a stunning church that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Siena Cathedral, an interesting church that offers a unique experience. Be sure to also explore Pubblico Palace, a nearby palace, highly recommended by other travelers. End your self-guided tour at Piazza Del Campo, a romantic public square and the perfect final attraction in Siena.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for a true cultural experience.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day5

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

On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Fasten your seatbelt and make your way to your next stop — Florence, home to many well-known sights in the region. Keep in mind that your travel time from Siena to Florence may take around 1 hour 3 min without traffic disruptions. Upon arrival in Florence, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Piazzale Michelangelo. Spend some time admiring the symbolic features of the observation deck before you continue to your next stop. Then, head to Bargello National Museum. This up-and-coming museum is a traveler-favorite in the city.

If you're keen to see more, continue to Basilica Of Santa Croce In Florence. Feed your curiosity by learning something new about the church. Next, take your journey to Uffizi Gallery, an astonishing art gallery. Conclude your sightseeing at Ponte Vecchio, known for its romantic features.

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

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

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

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

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Day6

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

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Pitti Palace is an ideal stop early in the day. This captivating palace is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Florence 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 Galleria Dell'accademia, a notable art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Central Market and Basilica Di Santa Maria Novella, Firenze (fi).

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

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.

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

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Day7

Day 7

  • Florence
  • Pisa
  • Lucca
  • 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

On day 7 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 14 min. Pisa welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Battistero Di San Giovanni, an underrated church that everyone visiting Pisa should see. Next, head to Piazza Del Duomo, Pisa. This stunning public square is one of the most wondrous attractions in the region.

If you're keen to see more, don’t miss out on Leaning Tower Of Pisa, a breathtaking monument popular among locals as well as travelers.

Set your GPS to Lucca and hit the road. Expect a journey of approximately 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Lucca beckons with new experiences!

Spend your afternoon discovering Guinigi Tower, an often recommended monument known for its visually striking features. Next, continue your sightseeing at San Michele In Foro, a locally appreciated church.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Mura Di Lucca and uncover the details of this romantic historical landmark.

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

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

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 your delicious meal, get a taste of the vibrant nightlife with a visit to Gosh*, known for its inviting atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another great option if you’re looking for a place to get the night started. Similarly, Quelo Bar provides a great setting to enjoy the night away.

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

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Day8

Day 8

  • Florence
  • Orvieto
  • 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

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Orvieto. At the end of the day, you’ll unwind at one of the finest accommodations in Perugia, where you'll spend 1 night.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Orvieto. This drive usually takes around 1 hour 54 min, without any stops or traffic disruptions.

Savor the day by heading to Well Of St. Patrick, a popular monument that draws visitors from near and far.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Orvieto. Expect your car journey to take a minimum of 1 hour 54 min. When you arrive in Orvieto, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Orvieto Cathedral and explore the symbolic features. Next, make your way to Museo Dell'opera Del Duomo, another highlight in Orvieto. When you’re done exploring the museum, continue to Orvieto Underground, a heritage-rich cave system.

Nearby, you will also find Torre Del Moro Orvieto. This beloved monument is a top place to see in the area. Lastly, head to Pozzo Della Cava, a heritage-rich cave that is perfect for some final exploring in the village.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 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 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 your delicious meal, get a taste of the vibrant nightlife with a visit to Punto Di Vista, known for its inviting atmosphere.

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

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Day9

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 breathtaking monument before you head out.

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.

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

Treat yourself to a delicious dinner at Ristorante IL CANTINONE Perugia, an excellent option for tonight's dining. Looking for something different? Locanda Del Bartoccio offers a tantalizing alternative with its diverse 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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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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