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

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Florence is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Piazzale Michelangelo, a spectacular observation deck that is worthwhile a visit in the city. Nearby, you’ll find Ponte Vecchio, enchanting visitors with its visually striking appeal. Continue your exploration at Uffizi Gallery. This art gallery is one of the city’s most top-rated spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Palazzo Vecchio. After exploring the palace, head to the impressive Piazza Della Signoria. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Galleria Dell'accademia, a place of detailed interest in Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Bring home unique finds from Florence's bustling shopping hub, Via de' Tornabuoni. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via de' Tornabuoni offers plenty of options, including primary services, unique landmarks, and community events.

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

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Greve in Chianti 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 2 nights.

Get ready to discover some of the most iconic wonders in Florence, including a castle, a church, a historical landmark, a palace, a public square and much more! Start your day at Castle Of Verrazzano. This history-steeped castle is an increasingly popular place to see in Florence. Then, wander over to Basilica Of San Domenico. If picture-perfect sites excite you, this church will be right up your alley. Nearby, you’ll also find Fontebranda. This eye-catching historical landmark is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Siena Cathedral is an interesting spot in the town that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the culturally significant Pubblico Palace. Take a moment to appreciate the fascinating details of this increasingly popular palace. Wrap up your self-guided tour of Florence's top attractions with a visit to Piazza Del Campo.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Siena's best restaurants.

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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

On day 4 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience San Gimignano, Pienza, and San Quirico d'Orcia to the fullest today with this curated day itinerary!

Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Siena. Begin your sightseeing with Porta San Giovanni. This worthwhile monument is one of the top attractions in the village. Proceed to Piazza Del Duomo, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Palazzo Comunale, Pinacoteca, Torre Grossa. This up-and-coming museum is a traveler-favorite. Not far away, you’ll find Chiesa Di Sant'agostino, another key site on your sightseeing itinerary. Palazzo Piccolomini, Pienza is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Chapel Vitaleta and uncover why it's recognized as one of the village's most underrated attractions.

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

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.

Have a fantastic dining experience at Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink. Similarly, Bar Pinacoteca is well-suited for those looking to unwind in a social setting. San Paolo Pub is another excellent spot to enjoy a nightcap after a delightful meal.

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

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of 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 3 nights.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Colosseum, an iconic archeological site in the city. Then, head to Arch Of Constantine and soak in the ambiance of this breathtaking monument.

There are many interesting places to see in Siena, and when you are ready for more, go to Roman Forum. This is one of the city’s most iconic UNESCO world heritage-listed spots of interest. After exploring the archeological site, visit the widely recognized Spanish Steps. Not far away, you'll also find Piazza Di Spagna. This public square is a romantic highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Altare Della Patria, a well-known monument in the city.

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.

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

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Say good night to Rome and look forward to another great day of your road trip in Italy!

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Rome for your remaining 2 nights in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Vatican City and Rome.

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is St. Peter's Basilica.

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 Vatican Museums. Next, make your way to Castel Sant'angelo to add another highlight to your day. After that, visit Trevi Fountain, a world-famous monument that’s sure to impress. 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.

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

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 7 of your road trip, you’ll start and end your day in Rome, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Rome and Tivoli. You still have 1 night left in Rome.

Rome is brimming with adventures. Today’s wonderful stops include a public square, a monument, a park, a palace and much more! Begin your sightseeing adventure at the world-famous Piazza Navona and allow yourself time to explore. Just a short distance away you'll find your next stop, Pantheon, an inviting monument that draws visitors from far and near.

Continue your journey to Piazza Del Popolo, one of the city’s most spectacular spots that you shouldn’t miss. Another great site to visit is the top-rated Villa Borghese. When you're finished at the park, Villa D'este awaits your visit. This palace is a history-steeped highlight on today's itinerary.

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

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 meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Rome. Some of the village’s most loved attractions await! Well Of St. Patrick is the perfect place to start. This monument is one of the most notable places to visit in Rome. Next, head to Orvieto Cathedral, a notable church, known for its history-steeped features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Museo Dell'opera Del Duomo. This instagrammable museum is a highly recommended experience. Nearby, you'll also find Orvieto Underground and Torre Del Moro Orvieto. Visit these for an interesting touch to your journey. Finish the day with a visit to Pozzo Della Cava, an instagrammable cave in Rome.

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.

As you explore more of Florence, 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.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

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.

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