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

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Explore the best of Italy on a 8-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Pisa, Florence, Siena, San Gimignano, Castelnuovo Berardenga, Greve in Chianti, Santa Maria degli Angeli, Perugia, Orvieto, and Lucca. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. 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 got 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. 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 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, 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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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Knights' Square
Leaning Tower of PisaPiazza del Duomo, PisaBasilica of Santa Croce in FlorenceUffizi GalleryPonte Vecchiopiazza della Signoria
Basilica of Santa Maria NovellaCentral MarketGalleria dell'AccademiaCathedral of Santa Maria del Fiorepiazzale MichelangeloOltrarno
Siena Cathedralpiazza del CampoTower of MangiaBasilica of San DomenicoPorta San GiovanniPiazza del Duomo, San Gimignano
Fèlsina S.P.A.Castello di BrolioCastle of VerrazzanoVilla Calcinaia - Conti Capponi
Basilica of San Francesco d'AssisiPiazza del ComuneRocca MaggiorePerugia CathedralPiazza IV NovembreThe Fontana Maggiore
Well of St PatrickOrvieto CathedralPozzo della CavaWalls of LuccaPiazza dell'Anfiteatro
Palazzo Blu

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Day 1

Day 1

  • Pisa - Arrival day
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  • Knights' Square
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Your road trip adventure in Italy begins as soon as you reach Pisa and pick up your car. You’ll stay in Pisa for 1 night 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.

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

Treat yourself to a delicious dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, an excellent option for tonight's dining. Looking for something different? il Mercante offers a tantalizing alternative with its diverse menu. And don’t miss La Ghiotteria. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Pisa.

Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 2

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
  • More

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Pisa and 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 2 nights.

Get ready for a day filled with fun adventures, scenic views, and picturesque spots in the charming city of Pisa. Your adventure starts at Leaning Tower Of Pisa, a world-famous local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This globally renowned public square is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Pisa's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Of Santa Croce In Florence. This photogenic church offers a fascinating experience that many visitors find memorable. Uffizi Gallery is also worth visiting, along with Ponte Vecchio. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Della Signoria. This widely recognized public square provides a fitting finale to your sightseeing.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

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.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 3

Day 3

  • Florence
  • More

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
  • More

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Today’s itinerary in Florence covers several incredible sights, including a church, a food market, an art gallery, an observation deck and much more! Start your adventure at Basilica Di Santa Maria Novella, Firenze (fi). This locally renowned church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the photogenic wonders of Central Market, a must-see food market 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 Galleria Dell'accademia. This popular art gallery offers an enriching experience. For a change of pace, head to Cathedral Of Santa Maria Del Fiore, where you can take in inviting features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo. These sights offer a fulfilling end to a perfect day.

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 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 and reflect on the day's adventures.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight 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.

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

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Day 4

Day 4

  • Florence
  • Siena
  • More

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
  • More

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. 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 2 nights.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most locally renowned attractions included on the itinerary is Siena Cathedral. This visually striking church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Campo and learn what makes this UNESCO world heritage-designated public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the intriguing Tower Of Mangia. After exploring the monument, head to Basilica Of San Domenico. This intriguing church is a highlight in Florence. As your day continues, stop by Porta San Giovanni, known for its breathtaking features. Lastly, don’t forget to check out the increasingly popular Piazza Del Duomo. Enjoy exploring this incredible public square at your own pace.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 Siena. 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 Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 5

Day 5

  • Siena
  • More

Drive 142 km, 2 hours 55 min

  • Fèlsina S.P.A.
  • Castello di Brolio
  • Castle of Verrazzano
  • Villa Calcinaia - Conti Capponi
  • More

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

Get ready to discover some of the most iconic wonders in Siena, including a winery and a castle. Start your day at Fèlsina S. P. A. This romantic winery is a curiosity-inducing place to see in Siena. Then, wander over to Castello Di Brolio. If awe-inspiring sites excite you, this castle will be right up your alley. Nearby, you’ll also find Castle Of Verrazzano. This visually striking castle is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Villa Calcinaia - Conti Capponi is an underrated spot in the village that will captivate you with its unique charm.

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 an authentic adventure.

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Pinacoteca, a bar that offers unique local touches. Likewise, San Paolo Pub provides an excellent alternative for a fun evening.

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

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Day 6

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
  • More

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 vibrant destinations - Santa Maria degli Angeli and Perugia. 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.

Savor the day by visiting some of the best places to see in Siena, including a church, a public square, a castle, a monument and much more! Start your adventure at Basilica Of San Francesco D'assisi. This notable church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Comune located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Rocca Maggiore. Its visually striking features will captivate you. After the castle, continue your tour of the town with a visit to Perugia Cathedral. Visitors usually appreciate the monumental features of this church. Next up is Piazza Iv Novembre, a highly recommended public square. For a change of pace, head to The Fontana Maggiore. As one of the most up-and-coming attractions in Siena, this monument is the perfect place to end your self-guided sightseeing tour.

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.

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 delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

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.

Savor another day of unforgettable experiences in Italy!

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Day 7

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
  • More

On day 7 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Orvieto and Lucca. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and photo-friendly spots. Whether you decide to explore Perugia on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Well Of St. Patrick is the first of them. Spend some time admiring this picture-perfect monument before continuing your journey. Orvieto Cathedral is your next stop. This interesting church is one of the best-rated sights in Perugia.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Pozzo Della Cava. This standout cave is a sight to behold. To round off your sightseeing experience, visit Mura Di Lucca and Piazza Dell'anfiteatro.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

As you explore more of Pisa, 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.

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Locanda Dei Pisani Doc Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Baribaldi Pisa, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a fulfilling meal, continue your evening at Bar Mocambo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tree offers a welcoming atmosphere for easing into the nightlife. Similarly, Chupiteria provides an excellent environment for a relaxed and enjoyable evening.

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

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Day 8

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. This is your chance to catch a last glimpse of Pisa 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 Palazzo Blu, a heritage-rich art gallery before you head out.

On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

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

Enjoy a lovely meal at Restaurant -Pizzeria Il Mio Capriccio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante alle Bandierine is another top choice with a popular menu.

You’ll then say farewell to Pisa. 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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