One-Week Italy Self-Drive Road Trip With Itinerary from Florence traveling west to Lucca, Montefioralle, Siena, and Volterra

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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 Florence, Pisa, Lucca, Greve in Chianti, Castellina in Chianti, San Donato in Poggio, Montefioralle, Siena, San Gimignano, Volterra, and Abbadia Isola. 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 3 nights in Florence, 1 night in Lucca, 1 night in Montefioralle, 1 night in Siena, and 1 night in Volterra. 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. Leaning Tower Of Pisa and Piazza Del Duomo, Pisa are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazzale Michelangelo, learn more about the unique Cathedral Of Santa Maria Del Fiore, and immerse yourself in the vibrant atmosphere of Piazza Della Signoria.

As you hit the open road and drive through Florence, Pisa, Lucca, Greve in Chianti, Castellina in Chianti, San Donato in Poggio, Montefioralle, Siena, San Gimignano, Volterra, and Abbadia Isola, 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
Central Market
Brunelleschi's domeCathedral of Santa Maria del FiorePiazza della Repubblicapiazza della SignoriaUffizi Gallery
Pisa CathedralPiazza del Duomo, PisaLeaning Tower of PisaPiazza dell'AnfiteatroPiazza Napoleone
Castle of VerrazzanoPoggio AmorelliRocca di Castellina in ChiantiOsservatorio Polifunzionale del Chianti
Fortezza MediceaPalazzo SalimbeniBasilica of San DomenicoSiena Cathedralpiazza del Campo
Porta San GiovanniSanGimignano1300Piazza del Duomo, San GimignanoCathedral of Santa Maria AssuntaParco Archeologico "Enrico Fiumi"
Abbazia dei Santi Salvatore e CirinoAbbey of San GalganoBasilica of Santa Croce in FlorenceGalleria dell'Accademia
piazzale Michelangelo

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Day 1

Day 1

  • Florence - Arrival day
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  • Central Market
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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 2 nights immersing yourself in Florence's charm before embarking on the next leg of your journey.

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 Central Market, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Florence. Make yourself at home and enjoy some downtime 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 Florence, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San 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.

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.

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 1 km, 24 min

  • Brunelleschi's dome
  • Cathedral of Santa Maria del Fiore
  • Piazza della Repubblica
  • piazza della Signoria
  • Uffizi Gallery
  • More

Day 2 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a church, a public square, an art gallery and much more! Begin your adventure at Brunelleschi's Dome. This is a curiosity-inducing monument you should not miss. Another must-see is Cathedral Of Santa Maria Del Fiore, an extraordinary church in Florence.

When you’re ready for the next sight, head to Piazza Della Repubblica. From there, take a leisurely stroll to Piazza Della Signoria, another of the city’s spectacular attractions. We recommend continuing your self-guided tour at Uffizi Gallery, a romantic place of interest in the city.

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 delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Savor another day of unforgettable experiences in Italy!

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Day 3

Day 3

  • Florence
  • Lucca
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Drive 107 km, 2 hours 5 min

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Lucca. At the end of the day, you will enjoy the comforts of a top-rated hotel in Lucca, which will be your home away from home for 1 night.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most intriguing attractions included on the itinerary is Pisa Cathedral. This stunning church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo, Pisa and learn what makes this breathtaking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Leaning Tower Of Pisa. After exploring the monument, head to Piazza Dell'anfiteatro. This interesting public square is a highlight in Florence. Lastly, don’t forget to check out the notable Piazza Napoleone. 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 Lucca. Check in and spend some time relaxing before you head out to tour the city.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Lucca. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at Gli Orti di Via Elisa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bar Caffè Ristretto? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Schiaffino as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Lucca.

Round off your dining experience by visiting Lebowski - Cocktail Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Blend, a bar catering to every mood and preference. Franklin'33 likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 4

Day 4

  • Lucca
  • Montefioralle
  • More

Drive 153 km, 2 hours 47 min

  • Castle of Verrazzano
  • Poggio Amorelli
  • Rocca di Castellina in Chianti
  • Osservatorio Polifunzionale del Chianti
  • 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 3 vibrant destinations - Greve in Chianti, Castellina in Chianti, and San Donato in Poggio. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Montefioralle. You will spend 1 night here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Lucca. Some of the town’s most loved attractions await. Castle Of Verrazzano is the perfect place to start. This castle is one of the most locally appreciated places to visit in Lucca. Next, head to Poggio Amorelli, an up-and-coming winery, known for its romantic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Rocca Di Castellina In Chianti. This visually striking castle offers a unique experience that is highly recommended. Meanwhile, Osservatorio Polifunzionale Del Chianti adds its own distinct charm to your journey.

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

Enjoy a lovely dining experience at La Castellana, a popular restaurant in Montefioralle. This acclaimed establishment has earned the admiration of countless food lovers in the city.

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

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Day 5

Day 5

  • Montefioralle
  • Siena
  • More

Drive 58 km, 1 hour 33 min

  • Fortezza Medicea
  • Palazzo Salimbeni
  • Basilica of San Domenico
  • Siena Cathedral
  • piazza del Campo
  • More

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Siena, 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 1 night.

Brace yourself for today’s incredible lineup of attractions in Montefioralle, featuring family-friendly attractions, scenic views, and photo-friendly spots. Start at Fortezza Medicea (siena), an increasingly popular monument in the city. Then, head to Palazzo Salimbeni and soak in the ambiance of this instagrammable palace.

There are many interesting places to see in Montefioralle and when you are ready for more, go to Basilica Of San Domenico. This is one of the city’s most up-and-coming spots. After exploring the church, visit the locally renowned Siena Cathedral. Before wrapping up your self-guided sightseeing tour, head to the top-rated Piazza Del Campo, a top-rated public square in the city.

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

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

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

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

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Day 6

Day 6

  • Siena
  • Volterra
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Drive 75 km, 1 hour 43 min

  • Porta San Giovanni
  • SanGimignano1300
  • Piazza del Duomo, San Gimignano
  • Cathedral of Santa Maria Assunta
  • Parco Archeologico "Enrico Fiumi"
  • More

On day 6 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 San Gimignano and Volterra. In the evening, you’ll end up in Volterra, where you will stay for 1 night.

Start by visiting Porta San Giovanni, a prime spot to begin your journey. This culturally significant monument is sure to impress. Next on your list is Sangimignano1300, another must-visit landmark and intriguing museum renowned for its heritage-rich features.

While exploring and sightseeing, take time to savor the ambiance of Siena by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Piazza Del Duomo. This inviting public square is a remarkable attraction that offers a unique experience. Cathedral Of Santa Maria Assunta also adds charm to your journey, and Parco Archeologico "enrico Fiumi" wraps up your day with its standout appeal.

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

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

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

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Day 7

Day 7

  • Volterra
  • Florence
  • More

Drive 168 km, 3 hours 35 min

  • Abbazia dei Santi Salvatore e Cirino
  • Abbey of San Galgano
  • Basilica of Santa Croce in Florence
  • Galleria dell'Accademia
  • More

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Abbadia Isola, San Galgano, and Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Savor the day by visiting some of the best places to see in Volterra, including a monastery, a church, and an art gallery. Start your adventure at Abbazia Dei Santi Salvatore E Cirino. This frequently visited monastery is a must-visit for travelers looking for a unique holiday experience. Make your way to Abbey Of San Galgano located in Volterra for an enchanting atmosphere.

Next, immerse yourself in the setting of Basilica Of Santa Croce In Florence. Its culturally significant features will captivate you. After the church, continue your tour of the village with a visit to Galleria Dell'accademia. This art gallery has a heritage-rich appeal.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 delicious meal 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.

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

  • Florence - Departure day
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  • piazzale Michelangelo
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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.

If you're up for some more sightseeing, begin at Piazzale Michelangelo. This extraordinary observation deck is a popular place to see in the city.

Make the most of your final day in Italy by visiting Florence’s iconic markets and shopping establishments in the buzzing San Lorenzo Market. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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 Djària - American Bar, 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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