5-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena and Rome
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Experience the freedom of the open road in Italy as you embark on an unforgettable 5-day road trip! This experience caters to every traveler, featuring destinations like Florence, Siena, Montepulciano, Rome, and Orvieto.
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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Day 1
- Florence - Arrival day
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- piazzale Michelangelo
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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 1 night 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 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.
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.
Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.
Raise a toast to the start of your 5-day road trip in Italy!
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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On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Florence and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.
Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a historical landmark, an art gallery, a church, a palace, a public square and much more! Begin your adventure at Ponte Vecchio. This is a globally renowned historical landmark you should not miss. Another must-see is Uffizi Gallery, a spectacular art gallery in Florence.
When you’re ready for the next sight, head to Basilica Of Santa Croce In Florence. From there, take a leisurely stroll to Siena Cathedral, another of the city’s captivating attractions. We recommend continuing your self-guided tour at Pubblico Palace, an UNESCO world heritage-designated place of interest in the city. If time allows, add Piazza Del Campo to your itinerary. This widely recognized public square offers the perfect finishing touch to your day in Florence.
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.
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.
Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.
Get a good night's sleep and look forward to another great day on the road in Italy!
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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Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Montepulciano and Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 1 night.
Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea. This increasingly popular castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Trevi Fountain, one of the town’s best highlights.
Next, check out Pantheon, one of the most globally renowned places to see in Siena. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Navona. Wander around and soak in the visually striking atmosphere this public square offers.
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.
After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.
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 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.
Raise your glass to another unforgettable day in Italy!
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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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 and Orvieto. In the evening, you’ll end up in Florence, where you will stay for 1 night.
Today’s route brings fun adventures, scenic views, and picturesque spots. The first attraction of today is Roman Forum. This globally renowned archeological site is a picture-perfect place to see in Rome. Continue your discovery at Colosseum, a culturally significant archeological site with stories to tell.
As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Orvieto Cathedral. This notable church offers a history-steeped encounter with Rome. Next, make your way to Well Of St. Patrick to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.
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.
Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.
Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.
Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!
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 visually striking 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.
Enjoy a lovely meal at Ristorante Buca Mario, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Agricola Toscana is another top choice with a popular 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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