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.

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.

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 5-day road trip in Italy!

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Day 2

Day 2

  • Florence
  • Arezzo
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Drive 77 km, 1 hour 21 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazza della Repubblica
  • Cathedral of Santa Maria del Fiore
  • More

Dive into day 2 of your remarkable road trip in Italy. Today you will explore 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 Arezzo. You’ll stay here for 1 night.

Florence is brimming with adventures. Today’s wonderful stops include a public square, an art gallery, a historical landmark, a church and much more! Begin your sightseeing adventure at the extraordinary Piazza Della Signoria and allow yourself time to explore. Just a short distance away you'll find your next stop, Uffizi Gallery, a romantic art gallery that draws visitors from far and near.

Continue your journey to Ponte Vecchio, one of the city’s most world-famous spots that you shouldn’t miss. Another great site to visit is the locally renowned Piazza Della Repubblica. When you're finished at the public square, Cathedral Of Santa Maria Del Fiore awaits your visit. This church is a symbolic highlight on today's itinerary.

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.

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

Set out on a gastronomic journey in Arezzo by reserving a table at Octavin. Renowned for its 1-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. Looking for something different? La Clandestina offers a tantalizing alternative with its diverse menu. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Arezzo.

After savoring a delicious meal, step into the vibrant nightlife at Liquid Bar, where the evening is just getting started.

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

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Day 3

Day 3

  • Arezzo
  • Rome
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Drive 251 km, 3 hours 41 min

  • San Francesco, Arezzo
  • piazza Grande
  • Arezzo Cathedral
  • Hermitage "Le Celle"
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Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Arezzo and Cortona. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 1 night here for some well-deserved relaxation.

A blend of fun adventures, photo-friendly spots, and history-rich sites await you in Arezzo on today’s itinerary. First up is the up-and-coming church, San Francesco, Arezzo. Afterward, continue to Piazza Grande, a public square every traveler should visit.

As you explore Arezzo’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Arezzo Cathedral. This beloved church is an essential stop. Following that, head to Hermitage "le Celle", another must-visit site that will enhance your experience.

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

Have a memorable dining experience in Rome by booking a table at La Pergola, renowned as a 3-star Michelin restaurant presenting an exceptional mediterranean and contemporary menu. For a different culinary experience in Rome, Il Pagliaccio shines as one of the top destinations, known for its delicious creative and innovative cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Enoteca La Torre is known as a top local spot for its delicious mediterranean and creative cuisine in Rome. This 2-star Michelin awardee is a highly recommended choice for an unforgettable meal.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

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

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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

On day 4 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 Florence, where you will stay for 1 night.

Get ready to discover some of the most iconic wonders in Rome, including a public square, an archeological site, and a monument. Start your day at Capitoline Hill. This majestic public square is a captivating place to see in Rome. Then, wander over to Roman Forum. If respected sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Colosseum. This culturally significant archeological site is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pantheon is an iconic spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the culturally significant Trevi Fountain. Take a moment to appreciate the fascinating details of this iconic monument.

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

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.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, 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

  • 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, we recommend visiting Piazzale Michelangelo, a culturally significant observation deck before you head out.

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.

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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