5-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to Arezzo and Rome

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Explore the best of Italy on a 5-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Florence, Arezzo, Cortona, and Rome. 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 Arezzo, and 1 night in Rome. 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 Ponte Vecchio, and immerse yourself in the vibrant atmosphere of Roman Forum.

As you hit the open road and drive through Florence, Arezzo, Cortona, and Rome, 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
piazza della SignoriaUffizi GalleryPonte VecchioPiazza della RepubblicaCathedral of Santa Maria del Fiore
San Francesco, Arezzopiazza GrandeArezzo CathedralHermitage "Le Celle"
Capitoline HillRoman ForumColosseumPantheonTrevi Fountain
piazzale Michelangelo

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Day 1

Day 1

  • Florence - Arrival day
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  • Central Market
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Your road trip adventure in Italy begins as soon as you reach Florence and pick up your car. You’ll stay in Florence for 1 night and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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.

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

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

Raise a toast to the start of your 5-day road trip in Italy!

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Day 2

Day 2

  • Florence
  • Arezzo
  • More

Drive 77 km, 1 hour 21 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazza della Repubblica
  • Cathedral of Santa Maria del Fiore
  • 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 Arezzo, where you will stay for 1 night.

Today’s itinerary in Florence covers several incredible sights, including a public square, an art gallery, a historical landmark, a church and much more! Start your adventure at Piazza Della Signoria. This impressive public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Uffizi Gallery, a must-see art gallery in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Ponte Vecchio. This iconic historical landmark offers an enriching experience. For a change of pace, head to Piazza Della Repubblica, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Cathedral Of Santa Maria Del Fiore and Cathedral Of Santa Maria Del Fiore. These sights offer a fulfilling end to a perfect day.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Arezzo. Arezzo 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 Arezzo. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Have a memorable dining experience in Arezzo by booking a table at Octavin, renowned as a 1-star Michelin restaurant presenting an exceptional creative menu. Immerse yourself in the culinary delights of La Clandestina, a popular restaurant in Arezzo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

Continue your evening by exploring the vibrant nightlife scene at Liquid Bar, a prime destination for a thrilling night out.

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

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Day 3

Day 3

  • Arezzo
  • Rome
  • More

Drive 251 km, 3 hours 41 min

  • San Francesco, Arezzo
  • piazza Grande
  • Arezzo Cathedral
  • Hermitage "Le Celle"
  • More

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

Today, you'll explore some of the most beautiful places in Arezzo, including a church, a public square, and a monastery. Start your day with a visit to San Francesco, Arezzo. This increasingly popular church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Grande, which may be one of the most romantic places you will experience today.

One of the best things about exploring Arezzo 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 Arezzo Cathedral, a locally appreciated church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Hermitage "le Celle".

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

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of mediterranean and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative and innovative 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 Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean and creative menu. With a 2-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 Rome.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

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Day 4

Day 4

  • Rome
  • Florence
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Drive 281 km, 3 hours 49 min

  • Capitoline Hill
  • Roman Forum
  • Colosseum
  • Pantheon
  • Trevi Fountain
  • 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 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Capitoline Hill. This well-known public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Roman Forum, one of the city’s best highlights.

Next, check out Colosseum, one of the most timeless places to see in Rome. This archeological site is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pantheon. Wander around and soak in the photogenic atmosphere this monument offers. Then, head to Trevi Fountain, a top-rated monument that adds another dimension to your day.

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.

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.

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 5

Day 5

  • Florence - Departure day
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  • piazzale Michelangelo
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Day 5 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 spectacular observation deck is a popular place to see in the city.

Maximize your last day in Italy and go on a shopping spree in Florence’s shopping center, the lively Via de' Tornabuoni. Browse for souvenirs to remind you of your wonderful journey in Italy. Discover boutiques with stylish fashion choices to upgrade your wardrobe. You can also explore high-end shops for luxury items.

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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