5-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena and Rome

Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
All inclusive app
Travel agent
24/7 fast service

Description

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!

Read more

Itinerary summary

See a summary of the itinerary that you can fully customize

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

Personalize your itinerary

Customize tours under each day and destination

Day 1

Day 1

  • Florence - Arrival day
  • More
  • piazzale Michelangelo
  • More

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.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Read more
Day 2

Day 2

  • Florence
  • Siena
  • More

Drive 80 km, 1 hour 35 min

  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
  • More

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

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Ponte Vecchio. This enchanting historical landmark is sure to ignite your curiosity. Next, dive into the instagrammable features of Uffizi Gallery, a must-visit art gallery in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Basilica Of Santa Croce In Florence, a captivating church. For a change of scene, check out Siena Cathedral, known for its history-steeped features. We also recommend visiting Pubblico Palace. This palace is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazza Del Campo, yet another astonishing attraction in Florence.

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 dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice 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.

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

Read more
Day 3

Day 3

  • Siena
  • Rome
  • More

Drive 250 km, 3 hours 51 min

  • Fortezza Medicea
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
  • More

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 - Montepulciano and Rome. 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.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the often recommended Fortezza Medicea, a visually striking castle in Siena. Next, go to Trevi Fountain.

After visiting Fortezza Medicea and Trevi Fountain, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Pantheon. This photogenic monument offers a unique experience. Piazza Navona is another noteworthy attraction worthwhile a visit.

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.

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

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio 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!

Read more
Day 4

Day 4

  • Rome
  • Florence
  • More

Drive 297 km, 4 hours 1 min

  • Roman Forum
  • Colosseum
  • Orvieto Cathedral
  • Well of St Patrick
  • 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 and Orvieto. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Roman Forum. This iconic archeological site is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Colosseum, one of the city’s best highlights.

Next, check out Orvieto Cathedral, one of the most locally renowned places to see in Rome. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Well Of St. Patrick. Wander around and soak in the culturally significant atmosphere this monument offers.

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

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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!

Read more
Day 5

Day 5

  • Florence - Departure day
  • More
  • Cathedral of Santa Maria del Fiore
  • More

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 Cathedral Of Santa Maria Del Fiore. This impressive church 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.

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!

Read more

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.