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

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Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
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photo of view of Florence,Italy.
photo of Landmarks of Italy - beautiful medieval town Lucca in Tuscany. City view from Guinigi tower.
aerial view of city and medieval Guinigi tower and its trees. Tuscany, Italy, Europe.
Porta San Pietro in Lucca - Tuscany,Italy
photo of view of  Panoramic view of Lucca medieval town with typical terracotta tiled roofs and narrow streets, Tuscany, Italy
photo of view of Amazing aerial view of Lucca medieval town in Tuscany, Italy.
photo of view of Lucca, Italy - View of Piazza San Giovanni and famous St Martin Cathedral tower in background, postcard of Tuscany.
photo of view of Detail exterior view of Lucca Cathedral (Duomo di Lucca, Cattedrale di San Martino) is a Roman Catholic cathedral dedicated to Saint Martin in Lucca, Italy. It is the seat of the Archbishop of Lucca.
photo of view of Italy, province of Lucca. Fancy Medieval Bridge - Devil's Bridge crosses the Serchio River. The green emerald cold water of the river reflects the ancient asymmetrical arches of the bridge
photo of view of Panorama of trees on the historic surrounding city wall of Lucca, Italy
photo of view of Lucca, Tuscany, Italy. San Michele in Foro church.
photo of view of Lucca, Italy. Façade and bell tower of Lucca Cathedral.
photo of view of   Old cozy street in Lucca, Italy. Lucca is a city and comune in Tuscany. It is the capital of the Province of Lucca
photo of view of Lucca, Italy - View of Piazza dell'Anfiteatro square through the arch, ancient Roman Empire amphitheater, famous Tuscany.
photo of  view of Lucca, Italy. Aerial view of the town.
photo of view of Lucca, Italy. Aerial view of the town.
Photo of Siena in Italy by SimonRei
Photo of Siena cathedral against a bright blue sky in Italy.
Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
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photo of view of historic buildings and landmarks in magnificent medieval Siena,Tuscany, Italy.
photo of view of Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view of Cathedral of the City of Siena in Tuscany region of Italy at sunset.
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photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view ofBeautiful view of campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Siena province, Italy
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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, Greve in Chianti, Castellina in Chianti, San Donato in Poggio, Montefioralle, Siena, San Gimignano, Volterra, and Abbadia Isola.

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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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.

Find your way to your hotel in Florence. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 2

Day 2

  • Florence
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Drive 1 km, 24 min

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

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Brunelleschi's Dome, an underrated monument in the city. Then, head to Cathedral Of Santa Maria Del Fiore and soak in the ambiance of this history-steeped church.

There are many interesting places to see in Florence, and when you are ready for more, go to Piazza Della Repubblica. This is one of the city’s most locally renowned visually striking spots of interest. After exploring the public square, visit the spectacular Piazza Della Signoria. Not far away, you'll also find Uffizi Gallery. This art gallery is a historic highlight in Florence.

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.

Visit Via de' Tornabuoni in Florence for an unforgettable shopping experience. Browse unique boutiques and luxurious stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Via de' Tornabuoni has to offer, including attractions, essential services, and vibrant community activities.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day 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

On day 3 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 Pisa and Lucca. In the evening, you’ll end up in Lucca, where you will stay for 1 night.

Prepare for a day full of fun adventures, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Pisa Cathedral. This often recommended church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Duomo, Pisa, one of the city’s best highlights.

Next, check out Leaning Tower Of Pisa, one of the most iconic places to see in Florence. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Dell'anfiteatro. Wander around and soak in the visually striking atmosphere this public square offers. Then, head to Piazza Napoleone, a top-rated public square that adds another dimension to your day.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Lucca. Lucca 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 Lucca. 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 Gli Orti di Via Elisa, a highly-rated dining destination in Lucca. If you're eager to try something different, consider Bar Caffè Ristretto, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Schiaffino. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Lucca this evening.

Extend your evening after a delightful meal by visiting Lebowski - Cocktail Bar, which offers the perfect atmosphere for a night out. Moreover, Blend is another popular option for a drink or two. Likewise, Franklin'33 also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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
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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.

Today’s itinerary in Lucca covers several incredible sights, including a castle, a winery, and an astronomical observatory. Start your adventure at Castle Of Verrazzano. This intriguing castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Poggio Amorelli, a must-see winery in the town.

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 Rocca Di Castellina In Chianti. This underrated castle offers an enriching experience. For a change of pace, head to Osservatorio Polifunzionale Del Chianti, where you can take in awe-inspiring features. These sights offer a fulfilling end to a perfect day.

At the end of the day, you will drive to Montefioralle, 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 Montefioralle. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely meal at La Castellana, a top-rated place to have dinner tonight.

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

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Day 5

Day 5

  • Montefioralle
  • Siena
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Drive 58 km, 1 hour 33 min

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

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. 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 1 night.

Montefioralle is brimming with adventures. Today’s wonderful stops include a monument, a palace, a church, a public square and much more! Begin your sightseeing adventure at the frequently visited Fortezza Medicea (siena) and allow yourself time to explore. Just a short distance away you'll find your next stop, Palazzo Salimbeni, an eye-catching palace that draws visitors from far and near.

Continue your journey to Basilica Of San Domenico, one of the city’s most underrated spots that you shouldn’t miss. Another great site to visit is the notable Siena Cathedral. When you're finished at the church, Piazza Del Campo awaits your visit. This public square is a history-steeped highlight on today's itinerary.

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 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 and reflect on the day's adventures.

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 excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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
  • 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 exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, San Gimignano and Volterra. When you’re not sightseeing, take time to relax at your selected hotel in Volterra, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and photo-friendly spots. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Porta San Giovanni is the first of them. Spend some time admiring this breathtaking monument before continuing your journey. Sangimignano1300 is your next stop. This locally appreciated museum is one of the best-rated sights in Siena.

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 Piazza Del Duomo. This visually striking public square is a sight to behold. To round off your sightseeing experience, visit Cathedral Of Santa Maria Assunta and Parco Archeologico "enrico Fiumi".

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

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

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

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Day 7

Day 7

  • Volterra
  • Florence
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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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Abbadia Isola, San Galgano, 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 1 night.

Brace yourself for today’s incredible lineup of attractions in Volterra, featuring family-friendly attractions, scenic views, and photo-friendly spots. Start at Abbazia Dei Santi Salvatore E Cirino, a beloved monastery in the village. Then, head to Abbey Of San Galgano and soak in the ambiance of this symbolic monastery.

There are many interesting places to see in Volterra, and when you are ready for more, go to Basilica Of Santa Croce In Florence. This is one of the village’s most notable culturally significant spots of interest. After exploring the church, visit the locally renowned Galleria Dell'accademia.

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

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

Don’t miss out on dining 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 enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable 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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  • 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, we recommend visiting Piazzale Michelangelo, a culturally significant observation deck before you head out.

Maximize your last day in Italy and go on a shopping spree in Florence’s shopping center, the lively San Lorenzo Market. Browse for souvenirs to remind you of your wonderful journey 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 in the mood to try something new, consider Djària - American Bar, another top spot with a mouthwatering 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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