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.

Today’s itinerary in Florence covers several incredible sights, including an observation deck, a historical landmark, an art gallery, a palace, a public square and much more! Start your adventure at Piazzale Michelangelo. This widely recognized observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Ponte Vecchio, a must-see historical landmark 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 Uffizi Gallery. This famous art gallery offers an enriching experience. For a change of pace, head to Palazzo Vecchio, where you can take in enchanting features. Conclude your self-guided sightseeing tour with a visit to Piazza Della Signoria and Galleria Dell'accademia. These sights offer a fulfilling end to a perfect day.

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.

Visit Mercato Centrale in Florence for an unforgettable shopping experience. Browse unique and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Mercato Centrale has to offer, including attractions, essential services, and vibrant community activities.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day in Italy!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Greve in Chianti and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Bring your curiosity for today’s adventure around Florence. Some of the town’s most loved attractions await! Castle Of Verrazzano is the perfect place to start. This castle is one of the most curiosity-inducing places to visit in Florence. Next, head to Basilica Of San Domenico, an intriguing church, known for its historic 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 Fontebranda. This photogenic historical landmark is a highly recommended experience. Nearby, you'll also find Siena Cathedral and Pubblico Palace. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Campo, an awe-inspiring public square in Florence.

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

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.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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

On day 4 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in San Gimignano, Pienza, and San Quirico d'Orcia. You still have 1 night left in Siena.

Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Porta San Giovanni. This underrated monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Duomo, one of the village’s best highlights.

Next, check out Palazzo Comunale, Pinacoteca, Torre Grossa, one of the most worthwhile places to see in Siena. This museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Chiesa Di Sant'agostino. Wander around and soak in the culturally significant atmosphere this church offers. Then, head to Palazzo Piccolomini, Pienza, a top-rated palace that adds another dimension to your day. Finally, visit the intriguing Chapel Vitaleta, the last of our attraction recommendations for today.

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

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

Make sure to reserve a table at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo, 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 the enjoyment post-dinner at Charlie Mixology Bar Di Aldinucci Riccardo, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Pinacoteca offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out San Paolo Pub. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 3 nights here for some well-deserved relaxation.

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the globally renowned Colosseum, a picture-perfect archeological site in Siena. Next, go to Arch Of Constantine.

After visiting Colosseum and Arch Of Constantine, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Roman Forum. This historic archeological site offers a unique experience. Spanish Steps is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Di Spagna, one of the most symbolic places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by Altare Della Patria.

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.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Head back to your accommodation in Rome and get some rest in preparation for another magical 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 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.

Continue your journey to Vatican Museums, one of the city’s most iconic spots that you shouldn’t miss. Another great site to visit is the impressive Castel Sant'angelo. When you're finished at the castle, Trevi Fountain awaits your visit. This monument is a masterful highlight on today's itinerary.

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

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 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.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

On day 7 of your road trip, you’ll start and end your day in Rome, where you'll stay for 1 night more.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Piazza Navona. This visually striking public square is a highlight of any visit in the city. Then, enjoy Pantheon, another respected attraction that never fails to captivate visitors. Next, head over to Piazza Del Popolo, one of the city’s most top-rated attractions, known for its masterful features.

If you’re looking for more, spend time soaking in the atmosphere of Villa Borghese. This serene park is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Villa D'este, a captivating palace, and take a stroll around the area.

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

As you explore more of Rome, 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 delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Following your dinner, dive into the local bar culture at The Apartment Bar Roma. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Hotel Hassler Roma, the perfect place for those looking to experience the best of the nightlife.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Orvieto, 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 Florence. You’ll stay here for 1 night.

Start by visiting Well Of St. Patrick, a prime spot to begin your journey. This breathtaking monument is sure to impress. Next on your list is Orvieto Cathedral, another must-visit landmark and locally renowned church renowned for its visually striking features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Museo Dell'opera Del Duomo. This noteworthy museum is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Orvieto Underground, a frequently visited cave system. Nearby, you'll also find Torre Del Moro Orvieto, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Pozzo Della Cava and wrap up your day with its heritage-rich appeal.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence. 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 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 could also check for a table at Eataly Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

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