Travel packages in Italy

Road trips in Italy

One-Week Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, Siena, and Perugia

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Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina

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Explore the best of Italy on a remarkable 8-day road trip! Combine exploration with relaxation on a self-drive tour featuring Pisa, Florence, Siena, San Gimignano, Castelnuovo Berardenga, Greve in Chianti, Santa Maria degli Angeli, Perugia, Orvieto, and Lucca.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Pisa, 2 nights in Florence, 2 nights in Siena, and 1 night in Perugia. 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 Pisa, 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 Pisa, Florence, Siena, San Gimignano, Castelnuovo Berardenga, Greve in Chianti, Santa Maria degli Angeli, Perugia, Orvieto, and Lucca, 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

Pisa - Arrival day
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Knights' Square
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Welcome to Pisa, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night discovering what to see in Pisa before embarking on the next leg of your journey.

Pisa 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 Pisa. 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 Pisa, it's often a good idea to reserve a table in advance.

Raise a toast to the start of your 8-day road trip in Italy!

Day 2

Pisa
Florence
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Drive 91 km, 1 hour 57 min

Leaning Tower of Pisa
Piazza del Duomo, Pisa
Basilica of Santa Croce in Florence
Uffizi Gallery
Ponte Vecchio
piazza della Signoria
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Your itinerary for day 2 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

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.

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.

Relax and recharge in preparation for another adventurous day in Italy!

Day 3

Florence
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Drive 11 km, 1 hour 2 min

Basilica of Santa Maria Novella
Central Market
Galleria dell'Accademia
Cathedral of Santa Maria del Fiore
piazzale Michelangelo
Oltrarno
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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 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.

Savor another day of unforgettable experiences in Italy!

Day 4

Florence
Siena
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Drive 160 km, 3 hours

Siena Cathedral
piazza del Campo
Tower of Mangia
Basilica of San Domenico
Porta San Giovanni
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.

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.

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

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 142 km, 2 hours 55 min

Fèlsina S.P.A.
Castello di Brolio
Castle of Verrazzano
Villa Calcinaia - Conti Capponi
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Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Castelnuovo Berardenga, San Regolo, Greve in Chianti, and Greti. With 1 night to stay in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

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

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

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 159 km, 2 hours 43 min

Basilica of San Francesco d'Assisi
Piazza del Comune
Rocca Maggiore
Perugia Cathedral
Piazza IV Novembre
The Fontana Maggiore
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Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Santa Maria degli Angeli and Perugia. At the end of the day, you will retreat to the hotel of your choice in Perugia, where will spend 1 night.

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

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

Day 7

Perugia
Pisa
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Drive 346 km, 5 hours 8 min

Well of St Patrick
Orvieto Cathedral
Pozzo della Cava
Walls of Lucca
Piazza dell'Anfiteatro
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On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Orvieto and Lucca. When you’re not sightseeing, take time to relax at your chosen hotel in Pisa, where you’ll be staying for 1 night.

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

Pisa 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 Pisa.

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

Day 8

Pisa - Departure day
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Palazzo Blu
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Day 8 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.

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!

How it works

Book your journey with Europe’s biggest travel platform—expert itineraries, instant confirmation, and full flexibility with 24/7 support.

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.

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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