5-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena 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, Siena, Montepulciano, Rome, and Orvieto. 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 Siena, 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 Piazza Navona, and immerse yourself in the vibrant atmosphere of Ponte Vecchio.

As you hit the open road and drive through Florence, Siena, Montepulciano, Rome, and Orvieto, 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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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
piazzale Michelangelo
Ponte VecchioUffizi GalleryBasilica of Santa Croce in FlorenceSiena CathedralPubblico Palacepiazza del Campo
Fortezza MediceaTrevi FountainPantheonPiazza Navona
Roman ForumColosseumOrvieto CathedralWell of St Patrick
Cathedral of Santa Maria del Fiore

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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.

As afternoon approaches, head to your chosen hotel in Florence. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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

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Day 2

Day 2

  • Florence
  • Siena
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Drive 80 km, 1 hour 35 min

  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
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Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Florence and Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Florence. Begin your sightseeing with Ponte Vecchio. This wondrous historical landmark is one of the top attractions in the city. Proceed to Uffizi Gallery, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Basilica Of Santa Croce In Florence. This popular church is a traveler-favorite. Not far away, you’ll find Siena Cathedral, another key site on your sightseeing itinerary. Pubblico Palace is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Campo and uncover why it's recognized as one of the city's most widely recognized attractions.

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 explore more of Siena, 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.

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.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Maudit Pub is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Impero Siena ensures a night out tailored to your taste.

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 3

Day 3

  • Siena
  • Rome
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Drive 250 km, 3 hours 51 min

  • Fortezza Medicea
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Montepulciano and Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. 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. Fortezza Medicea is the first of them. Spend some time admiring this history-steeped castle before continuing your journey. Trevi Fountain is your next stop. This iconic monument 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 Pantheon. This standout monument is a sight to behold. To round off your sightseeing experience, visit Piazza Navona.

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

Don’t miss out on dining at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

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

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Day 4

Day 4

  • Rome
  • Florence
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Drive 297 km, 4 hours 1 min

  • Roman Forum
  • Colosseum
  • Orvieto Cathedral
  • Well of St Patrick
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Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Rome and Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Get ready for a day filled with fun adventures, breathtaking views, and picturesque spots in the charming city of Rome. Your adventure starts at Roman Forum, a globally renowned local hot spot. Another notable attraction to explore is Colosseum. This globally renowned archeological site is known for its picture-perfect appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Orvieto Cathedral. This romantic church offers a fascinating experience that many visitors find memorable. Well Of St. Patrick is also worth visiting.

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.

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

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 5

Day 5

  • Florence - Departure day
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  • Cathedral of Santa Maria del Fiore
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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 Cathedral Of Santa Maria Del Fiore, a symbolic church 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.

If you're in the mood to try something new, consider Agricola Toscana, 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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