9-Day Italy Self-Drive Road Trip With Itinerary from Florence to Verona, Milan, Venice, Arezzo, Rome, and Siena and surrounding area

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Explore the best of Italy on a 9-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Florence, Verona, Milan, Venice, Arezzo, Rome, Siena, and Pisa. 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 Florence, 1 night in Verona, 1 night in Milan, 1 night in Venice, 1 night in Arezzo, 1 night in Rome, and 1 night in Siena. 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. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of Piazza San Marco.

As you hit the open road and drive through Florence, Verona, Milan, Venice, Arezzo, Rome, Siena, and Pisa, 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
piazzale Michelangelo
piazza della SignoriaUffizi GalleryPonte VecchioCathedral of Santa Maria del FioreCentral Market
Verona ArenaCastelvecchio BridgeGardaland Resort
Duomo di MilanoGalleria Vittorio Emanuele IILa ScalaSempione Park
Rialto BridgePiazza San MarcoSt Mark's BasilicaDoge's Palace
Vatican MuseumsSaint Peter's SquareSistine ChapelSt Peter's Basilica

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Day 1

Day 1

  • Florence - Arrival day
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  • piazzale Michelangelo
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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 1 night 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 Piazzale Michelangelo, 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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

Raise a toast to the start of your 9-day road trip in Italy!

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Day 2

Day 2

  • Florence
  • Verona
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Drive 234 km, 3 hours 4 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • Central Market
  • More

On day 2 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 Florence. In the evening, you’ll end up in Verona, where you will stay for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, 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. Piazza Della Signoria is the first of them. Spend some time admiring this masterful public square before continuing your journey. Uffizi Gallery is your next stop. This spectacular art gallery 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 symbolic historical landmark is a sight to behold. To round off your sightseeing experience, visit Cathedral Of Santa Maria Del Fiore and Central Market.

At the end of the day, you will drive to Verona, 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 Verona's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy an outstanding dining experience at Osteria Mondo d'Oro, a Bib Gourmand restaurant offering an exceptional italian and seasonal menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Casa Perbellini 12 Apostoli, known for its delicious creative and contemporary cuisine. Another highly-recommended place to eat in Verona is Il Desco, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious italian contemporary menu.

To truly maximize your evening out, consider visiting Archivio after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to La Segreteria Café, another bar with an inviting ambiance. Similarly, Grande Giove Cocktail Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 3

Day 3

  • Verona
  • Milan
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Drive 158 km, 2 hours 31 min

  • Verona Arena
  • Castelvecchio Bridge
  • Gardaland Resort
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Verona and Ronchi, 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 Milan. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Verona, featuring fun adventures, romantic experiences, and scenic views. Start at Verona Arena, a globally renowned stadium in the city. Then, head to Castelvecchio Bridge and soak in the ambiance of this visually striking monument.

There are many interesting places to see in Verona, and when you are ready for more, go to Gardaland Resort. This is one of the city’s most widely recognized picture-perfect spots of interest.

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

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

Set out on a gastronomic journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. For a different taste, head over to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Il Luogo Aimo e Nadia, a highly rated local gem known for its exquisite italian contemporary and modern menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Nottingham Forest, known for its inviting atmosphere. Armani/bamboo Bar is another great option if you’re looking for a place to get the night started. Similarly, Mag Cafe provides a great setting to enjoy the night away.

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

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Day 4

Day 4

  • Milan
  • Venice
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Drive 276 km, 3 hours 27 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • La Scala
  • Sempione Park
  • More

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Milan. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 1 night.

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await! Duomo Di Milano Museum is the perfect place to start. This church is one of the most iconic places to visit in Milan. Next, head to Galleria Vittorio Emanuele Ii, a top-rated shopping mall, 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 La Scala. This history-steeped opera house is a highly recommended experience. Nearby, you'll also find Parco Sempione. Visit these for an interesting touch 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 Venice. Venice 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 Venice, 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.

Experience a symphony of flavors at Local in Venice by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Local delights its guests with its exceptional variety of meals showcasing delicious contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Wistèria, acclaimed for its delectable contemporary and venetian specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Quadri, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for modern cuisine in the city.

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

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

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Day 5

Day 5

  • Venice
  • Arezzo
  • More

Drive 331 km, 3 hours 45 min

  • Rialto Bridge
  • Piazza San Marco
  • St Mark's Basilica
  • Doge's Palace
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Venice. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Arezzo. You will spend 1 night here for some well-deserved relaxation.

Get ready to discover some of the most iconic wonders in Venice, including a historical landmark, a public square, a church, a palace and much more! Start your day at Rialto Bridge. This enchanting historical landmark is a globally renowned place to see in Venice. Then, wander over to Piazza San Marco. If visually striking sites excite you, this public square will be right up your alley. Nearby, you’ll also find St Mark's Basilica. This UNESCO world heritage-designated church is a favorite among visitors.

Venice offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Doge's Palace is an interesting spot in the city that will captivate you with its unique charm.

At the end of the day, you will drive to Arezzo, 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 Arezzo. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu. If you're eager to try something different, consider La Clandestina, another top spot with a tantalizing menu.

Continue the enjoyment post-dinner at Liquid Bar, a cherished local gathering spot renowned for its welcoming atmosphere.

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

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Day 6

Day 6

  • Arezzo
  • Rome
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Drive 228 km, 3 hours 15 min

  • Vatican Museums
  • Saint Peter's Square
  • Sistine Chapel
  • St Peter's Basilica
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On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 1 night.

Continue your journey to Sistine Chapel, one of the city’s most widely recognized spots that you shouldn’t miss. Another great site to visit is the wondrous St. Peter's Basilica.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. 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 Rome. 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.

Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

  • Rome
  • Siena
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Drive 243 km, 3 hours 31 min

  • Roman Forum
  • Colosseum
  • Piazza Navona
  • Pantheon
  • Trevi Fountain
  • 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 Rome. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Start by visiting Roman Forum, a prime spot to begin your journey. This picture-perfect archeological site is sure to impress. Next on your list is Colosseum, another must-visit landmark and globally renowned archeological site renowned for its picture-perfect features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Navona. This visually striking public square is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Pantheon, a wondrous monument. Nearby, you'll also find Trevi Fountain, ready to add 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 Siena. Siena 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. 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, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

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Day 8

Day 8

  • Siena
  • Florence
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Drive 216 km, 3 hours 30 min

  • piazza del Campo
  • Siena Cathedral
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Campo santo
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Dive into day 8 of your remarkable road trip in Italy. Today you will explore Siena and Pisa, 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.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a public square, a church, a monument, a cemetery and much more! Begin your adventure at Piazza Del Campo. This is an astonishing public square you should not miss. Another must-see is Siena Cathedral, a notable church in Siena.

When you’re ready for the next sight, head to Leaning Tower Of Pisa. From there, take a leisurely stroll to Piazza Del Duomo, Pisa, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Campo Santo, a breathtaking place of interest in the city.

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.

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!

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Day 9

Day 9

  • Florence - Departure day
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  • Oltrarno
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Day 9 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.

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.

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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