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

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Experience the freedom of the open road in Italy as you embark on an unforgettable 8-day road trip! This experience caters to every traveler, featuring destinations like Florence, Pisa, Lucca, Siena, San Gimignano, Castellina in Chianti, Santa Maria degli Angeli, Perugia, 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 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 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. 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 Florence, Pisa, Lucca, Siena, San Gimignano, Castellina in Chianti, Santa Maria degli Angeli, Perugia, 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
Cathedral of Santa Maria del Fiore
Galleria dell'Accademiapiazza della SignoriaPonte VecchioUffizi GalleryBasilica of Santa Croce in Florencepiazzale Michelangelo
Piazza del Duomo, PisaPisa CathedralLeaning Tower of PisaWalls of LuccaPiazza dell'Anfiteatro
Siena Cathedralpiazza del CampoTower of MangiaPorta San GiovanniSanGimignano1300Piazza del Duomo, San Gimignano
Castello di BrolioTumulo di MontecalvarioRocca di Castellina in Chianti
Basilica of San Francesco d'AssisiRocca MaggioreRocca PaolinaPerugia CathedralPiazza IV NovembreThe Fontana Maggiore
Well of St PatrickOrvieto CathedralOrvieto subterraneaTorre del Moro OrvietoPozzo della Cava
Oltrarno

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Day 1

Day 1

  • Florence - Arrival day
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  • Cathedral of Santa Maria del Fiore
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Say hello to Florence! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Florence for 3 nights before you continue your adventure!

Florence 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 Cathedral Of Santa Maria Del Fiore, 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

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

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Day 2

Day 2

  • Florence
  • More

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
  • More

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

Today’s well-planned self-sightseeing route offers several fun adventures, photo-friendly spots, and historic treasures. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Galleria Dell'accademia is the first of them. Spend some time admiring this history-steeped art gallery before continuing your journey. Piazza Della Signoria is your next stop. This extraordinary public square is one of the best-rated sights in Florence.

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 Ponte Vecchio. This enchanting historical landmark is a sight to behold. To round off your sightseeing experience, visit Uffizi Gallery and Basilica Of Santa Croce In Florence. If time allows, end your day with Piazzale Michelangelo, an enchanting observation deck that offers a memorable conclusion to your exploration.

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 explore more of Florence, 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 delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 3

Day 3

  • Florence
  • More

Drive 199 km, 3 hours 21 min

  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Leaning Tower of Pisa
  • Walls of Lucca
  • Piazza dell'Anfiteatro
  • More

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa and Lucca.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, breathtaking views, and photo-friendly spots. Start at Piazza Del Duomo, Pisa, a timeless public square in the city. Then, head to Pisa Cathedral and soak in the ambiance of this UNESCO world heritage-listed church.

There are many interesting places to see in Florence and when you are ready for more, go to Leaning Tower Of Pisa. This is one of the city’s most world-famous spots. After exploring the monument, visit the worthwhile Mura Di Lucca. Before wrapping up your self-guided sightseeing tour, head to the well-known Piazza Dell'anfiteatro, a well-known public square in the city.

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

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

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

Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

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Day 4

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
  • More

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, 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 Siena. You’ll stay here for 2 nights.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Siena Cathedral is the first of them. Spend some time admiring this romantic church before continuing your journey. Piazza Del Campo is your next stop. This spectacular public square is one of the best-rated sights in Florence.

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 Tower Of Mangia. This picture-perfect monument is a sight to behold. To round off your sightseeing experience, visit Porta San Giovanni and Sangimignano1300. If time allows, end your day with Piazza Del Duomo, a visually striking public square that offers a memorable conclusion to your exploration.

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.

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

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Day 5

Day 5

  • Siena
  • More

Drive 73 km, 1 hour 58 min

  • Castello di Brolio
  • Tumulo di Montecalvario
  • Rocca di Castellina in Chianti
  • More

On day 5 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Castello Di Brolio. This history-steeped castle is a highlight of any visit in the hamlet. Then, enjoy Tumulo Di Montecalvario, another symbolic attraction that never fails to captivate visitors. Next, head over to Rocca Di Castellina In Chianti, one of the hamlet’s most intriguing attractions, known for its romantic features.

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

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.

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.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 6

Day 6

  • Siena
  • Perugia
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Drive 158 km, 2 hours 48 min

  • Basilica of San Francesco d'Assisi
  • Rocca Maggiore
  • Rocca Paolina
  • 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.

Prepare for a day full of family-friendly attractions, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Basilica Of San Francesco D'assisi. This well-known church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Rocca Maggiore, one of the town’s best highlights.

Next, check out Rocca Paolina, one of the most intriguing places to see in Siena. This historical landmark is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Perugia Cathedral. Wander around and soak in the culturally significant atmosphere this church offers. Then, head to Piazza Iv Novembre, a top-rated public square that adds another dimension to your day. Finally, visit the beloved The Fontana Maggiore, the last of our attraction recommendations for today.

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

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.

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 the enjoyment post-dinner at Tommi Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Valentina offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffe Dal Perugino. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 7

Day 7

  • Perugia
  • Florence
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Drive 244 km, 3 hours 41 min

  • Well of St Patrick
  • Orvieto Cathedral
  • Orvieto subterranea
  • Torre del Moro Orvieto
  • Pozzo della Cava
  • More

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Orvieto. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Today, you'll explore some of the most beautiful places in Perugia, including a monument, a church, a cave system, a cave and much more! Start your day with a visit to Well Of St. Patrick. This interesting monument is a must-visit in the village. When you’re ready for your next discovery, continue to Orvieto Cathedral, which may be one of the most history-steeped 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 Orvieto Underground, an often recommended cave system in the village. If you’re up for more discoveries, don’t forget to reserve some time for Torre Del Moro Orvieto and Pozzo Della Cava.

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.

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

Enjoy a delicious meal at Tijuana, a highly-rated dining destination in Florence. If you're eager to try something different, consider Djària - American Bar, another top spot with a tantalizing menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

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Day 8

Day 8

  • Florence - Departure day
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  • Oltrarno
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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 Florence before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

One of the best things to do on your last day 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.

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 Florence.

If you're eager to try something different, consider Essenziale, another top spot with a tantalizing menu.

You’ll then say farewell to Florence. 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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