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

Day 2 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Florence.

One of the most impressive attractions included on the itinerary is Piazzale Michelangelo. This awe-inspiring observation deck will help you start your sightseeing on top. Then, take a leisurely stroll to Ponte Vecchio and learn what makes this romantic historical landmark unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the impressive Uffizi Gallery. After exploring the art gallery, head to Palazzo Vecchio. This interesting palace is a highlight in Florence. As your day continues, stop by Piazza Della Signoria, known for its visually striking features. Lastly, don’t forget to check out the well-known Galleria Dell'accademia. Enjoy exploring this incredible art gallery at your own pace.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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 Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Take some time to reflect on your day and savor another beautiful night in Italy.

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Greve in Chianti and Siena. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 2 nights.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Greve in Chianti. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 46 min. Upon reaching Greve in Chianti, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Savor the day by heading to Castle Of Verrazzano, an up-and-coming castle that draws visitors from near and far.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Siena may take around 1 hour. Upon your arrival in Siena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Our first attraction recommendation in Siena is Basilica Of San Domenico, an intriguing church that draws attention for its majestic features. Spend some time soaking in the atmosphere before continuing to Fontebranda, a respected historical landmark that stands out in the town.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Siena Cathedral, a captivating church that offers a unique experience. Be sure to also explore Pubblico Palace, a nearby palace, highly recommended by other travelers. End your self-guided tour at Piazza Del Campo, a visually striking public square and the perfect final attraction in Siena.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Relax and look forward to more memorable moments to come!

On day 4 of your road trip, you’ll start and end your day in Siena, where you have 1 night left to stay.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to San Gimignano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 43 min. Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Spend your afternoon discovering Porta San Giovanni, a frequently visited monument known for its picture-perfect features. Next, continue your sightseeing at Piazza Del Duomo, an intriguing public square.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Palazzo Comunale, Pinacoteca, Torre Grossa and uncover the details of this culturally significant museum. Make sure to also explore Chiesa Di Sant'agostino, an up-and-coming church.

Continue your road trip and head to your next destination, Pienza. This car ride takes around 1 hour 37 min.

When you're ready for some sights, head to Palazzo Piccolomini, Pienza, an increasingly popular palace in Pienza. Explore its history-steeped features at your own pace before you continue your journey.

When you’re ready to jump back into the car and say goodbye to Pienza, you’ll hit the road in the direction of San Quirico d'Orcia. This drive usually takes around 17 min.

When you're ready for some sights, head to Chapel Vitaleta, a beloved church in San Quirico d'Orcia. Explore its history-steeped features at your own pace before you continue your journey.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

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 Siena, it's often a good idea to reserve a table in advance.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

After your meal, keep the night alive at a bar like Charlie Mixology Bar Di Aldinucci Riccardo, known for its lively atmosphere. Bar Pinacoteca is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, San Paolo Pub offers an excellent atmosphere for those looking to amp up the evening.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Rome, where you’ll be staying for 3 nights.

Set your GPS to Rome and hit the road. Expect a journey of approximately 2 hours 42 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Rome beckons with new experiences!

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Colosseum, a globally renowned archeological site that everyone visiting Rome should see. Next, head to Arch Of Constantine. This noteworthy monument is one of the most worthwhile attractions in the region.

If you're keen to see more, don’t miss out on Roman Forum, a culturally significant archeological site popular among locals as well as travelers. Spanish Steps is an excellent attraction to visit next. Spend some time learning more about this extraordinary public square before you continue your journey. Lastly, visit Piazza Di Spagna, an enchanting public square and a top attraction in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and relax before you head out to tour the city.

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

Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. 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 La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Almalu Trastevere provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Viminale Di Pepi Maurilio offers a memorable night with diverse drink options and excellent service.

Relax and recharge in preparation for another adventurous day in Italy!

On day 6 of your road trip, you’ll start and end your day in Rome, where you still have 2 nights left. You'll spend part of the day exploring places of interest outside the immediate city, including Vatican City and Rome.

Trastevere is one of the highlights of today. Take your time exploring this iconic neighborhood in Vatican City, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Castel Sant'angelo is an ideal stop early in the day. This impressive castle is a must-visit in the city. When you’re ready for your next discovery, continue to Trevi Fountain, which may be one of the most enchanting places you will experience today.

Vatican City’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 9 min. Vatican City welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to St. Peter's Basilica, a globally renowned major basilica that everyone visiting Vatican City should see. Next, head to Sistine Chapel.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

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.

Treat yourself to a delightful dinner at RomAntica, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Coso Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at DEROMA - Farine Romane as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Sant' Eustachio Caffè, known for its inviting atmosphere. Yellowsquare Rome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Portofino provides a great setting to enjoy the night away.

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

Greet day 7 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Rome, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Rome and Tivoli.

Visiting Piazza Navona is always a good idea. This iconic public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the instagrammable wonders of Pantheon, a must-see monument 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 Piazza Del Popolo. This famous public square offers an enriching experience. For a change of pace, head to Villa Borghese, where you can take in eye-catching features.

After soaking in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Tivoli. Expect your car journey to take a minimum of 44 min. When you arrive in Tivoli, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Villa D'este, a locally renowned palace that everyone visiting Tivoli should see.

When you’re done exploring for the day, you’ll return to Rome and your accommodation.

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

Enjoy a lovely dining experience at Hotel de Russie, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at La Taverna Italiana, 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 The Parrot Bar. It’s yet another ideal choice to enhance your time in Rome tonight.

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

Relax and recharge in preparation for another adventurous day in Italy!

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Orvieto are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Orvieto may take around 1 hour 35 min. Upon your arrival in Orvieto, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Well Of St. Patrick, a captivating monument known for its stunning features.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Orvieto. Your travel time is around 1 hour 35 min.

Spend your afternoon discovering Orvieto Cathedral, a captivating church known for its inviting features. Next, continue your sightseeing at Museo Dell'opera Del Duomo, an underrated museum.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Orvieto Underground and uncover the details of this photogenic cave system. Make sure to also explore Torre Del Moro Orvieto, an intriguing monument. For your last stop, consider Pozzo Della Cava, an eye-catching cave that many travelers find worth the detour.

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 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 Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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