Travel packages in Italy

Road trips in Italy

10-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to Siena, Perugia, and Orvieto

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Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.

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Escape the ordinary with this exciting 10-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 4 nights in Florence, 2 nights in Siena, 1 night in Perugia, and 2 nights in Orvieto. 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 Florence, 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. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Florence, Pisa, Lucca, Siena, San Gimignano, Castellina in Chianti, Santa Maria degli Angeli, Perugia, Orvieto, Bolsena, Rome, Montepulciano, San Quirico d'Orcia, and Montalcino, 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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Day 1

Florence - Arrival day
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Cathedral of Santa Maria del Fiore
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Welcome to Florence, 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 Florence before embarking on the next leg of your journey.

Florence is a beautiful city with plenty to discover. 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.

Raise a toast to the start of your 10-day road trip in Italy!

Day 2

Florence
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Drive 9 km, 1 hour 16 min

Galleria dell'Accademia
piazza della Signoria
Ponte Vecchio
Uffizi Gallery
Basilica of Santa Croce in Florence
piazzale Michelangelo
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You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

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.

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

Day 3

Florence
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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
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On day 3 of your road trip, you'll get the chance to experience Pisa and Lucca. At the end of the day, you'll drive back to Florence, where you still have 1 night left to stay.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

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

Day 4

Florence
Siena
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Drive 158 km, 2 hours 58 min

Siena Cathedral
piazza del Campo
Tower of Mangia
Porta San Giovanni
SanGimignano1300
Piazza del Duomo, San Gimignano
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On day 4 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Gimignano are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Siena. Siena 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

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

Day 5

Siena
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Drive 78 km, 1 hour 52 min

Rocca di Castellina in Chianti
Poggio Amorelli
Castello di Brolio
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Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Siena, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Castellina in Chianti and San Regolo.

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

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

Head back to your accommodation in Siena and get some rest to prepare for another magical day of your road trip in Italy.

Day 6

Siena
Perugia
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Drive 160 km, 2 hours 40 min

Basilica of San Francesco d'Assisi
Piazza del Comune
Rocca Maggiore
Perugia Sotterranea Accesso
The Fontana Maggiore
Piazza IV Novembre
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On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your chosen hotel in Perugia, where you’ll be staying for 1 night.

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

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.

Raise your glass to another unforgettable day in Italy!

Day 7

Perugia
Orvieto
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Drive 123 km, 2 hours 36 min

Orvieto Cathedral
Orvieto subterranea
Pozzo della Cava
Collegiata di Santa Cristina
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Your itinerary for day 7 of your road trip in Italy includes 2 stops and features some of the highlights of Orvieto and Bolsena. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 2 nights.

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

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

Head back to your accommodation in Orvieto and get some rest to prepare for another magical day of your road trip in Italy.

Day 8

Orvieto
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Drive 248 km, 3 hours 49 min

Colosseum
Roman Forum
Trevi Fountain
Pantheon
Piazza Navona
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Wake up to day 8 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Rome. With 1 night to stay in Orvieto, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

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

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

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

Day 9

Orvieto
Florence
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Drive 222 km, 3 hours 57 min

Fortezza Medicea
Cipressi di San Quirico d'Orcia
Fortress of Montalcino
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Dive into day 9 of your remarkable road trip in Italy. Today you'll explore 3 destinations, including Montepulciano, San Quirico d'Orcia, and Montalcino. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

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

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

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

Day 10

Florence - Departure day
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Oltrarno
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Day 10 of your road trip in Italy is your departure day. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing vacation.

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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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.

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.

We guarantee

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

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