9-Day Italy Self-Drive Road Trip With Itinerary from Rome to Florence, Siena, Greve in Chianti, and Perugia

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

One of the most iconic places you can visit today in Rome is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Today’s agenda in Rome includes a public square, a monument, and an archeological site. Spanish Steps is must-visit public square and a great starting point for the day. Next, continue your journey to Piazza Di Spagna, an iconic public square, located just a leisurely stroll away. Next, head to Trevi Fountain, an enchanting monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the world-famous Roman Forum. If you’re looking for more, Colosseum is also a world-famous attraction that is worthwhile a visit.

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.

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.

Treat yourself to a delicious dinner at RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Piazzale Michelangelo is the perfect place to start. This observation deck is one of the most famous places to visit in Rome. Next, head to Basilica Of Santa Croce In Florence, a notable church, known for its culturally significant 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 Uffizi Gallery. This historic art gallery is a highly recommended experience. Nearby, you'll also find Ponte Vecchio and Piazza Della Repubblica. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Della Signoria, a remarkable public square 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.

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Savor another day of unforgettable experiences in Italy!

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

Leaning Tower Of Pisa is must-visit monument and a great starting point for the day. Next, continue your journey to Putti Fountain, a curiosity-inducing fountain, located just a leisurely stroll away. Next, head to Piazza Del Duomo, Pisa, a culturally significant public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the often recommended Pisa Cathedral. If you’re looking for more, Porta San Pietro is also a curiosity-inducing attraction that is worthwhile a visit. Lastly, don’t miss Mura Di Lucca, a place of history-steeped interest in the city.

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

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

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

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences in Italy!

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, 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.

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Siena Cathedral. This popular church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Campo, one of the city’s best highlights.

Next, check out Tower Of Mangia, one of the most increasingly popular places to see in Florence. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Parco Della Rocca. Wander around and soak in the romantic atmosphere this park offers.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Castellina in Chianti. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Greve in Chianti. You will spend 1 night here for some well-deserved relaxation.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Rocca Di Castellina In Chianti is the first of them. Spend some time admiring this history-steeped castle before continuing your journey. Tumulo Di Montecalvario is your next stop. This increasingly popular archeological site is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Poggio Amorelli. This visually striking winery is a sight to behold.

When you’re done exploring for the day, you’ll drive to your hotel in Greve in Chianti. Check in and spend some time relaxing before you head out to tour the town.

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

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

On day 7 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 Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Today’s route brings fun adventures, breathtaking views, and photo-friendly spots. The first attraction of today is Basilica Of San Francesco D'assisi. This captivating church is a culturally significant place to see in Greve in Chianti. Continue your discovery at Rocca Maggiore, a romantic castle with stories to tell.

As you stroll around Greve in Chianti, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Perugia Sotterranea Accesso. This underrated cave system offers a respected encounter with Greve in Chianti. Next, make your way to Perugia Cathedral to add another highlight to your day. After that, visit Piazza Iv Novembre, a locally appreciated public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at The Fontana Maggiore, an underrated monument in the town. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Greve in Chianti.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Perugia. Perugia 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 Perugia's best restaurants.

Dine in style at Ristorante Settimo Sigillo, a top recommendation for dinner tonight. Or, for a change of pace, Caffè Baglioni boasts a menu that's sure to impress. Also, be sure to check out Bar Pellas. Known as a local hotspot, it’s a great choice for tonight in Perugia.

Unwind after your meal by stepping into Tommi Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Valentina offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffe Dal Perugino, another top-rated bar in the area.

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 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Orvieto. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 1 night.

Immerse yourself in Perugia’s rich culture with today's sightseeing itinerary. Start your journey at Orvieto Cathedral. This inviting church is sure to ignite your curiosity. Next, dive into the respected features of Orvieto Underground, a must-visit cave system in the town.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Pozzo Della Cava, an increasingly popular cave.

At the end of the day, you will drive to Rome, 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 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 Hotel de Russie, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Taverna Italiana offers an enticing alternative with its varied menu. Additionally, The Parrot Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Keep the evening going at The Apartment Bar Roma, a great choice for enjoying the after-dinner hours with a drink. You could also go to Hotel Hassler Roma, which offers a similarly pleasant setting and great drinks.

Raise your glass to another unforgettable day in Italy!