11-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to San Gimignano, Perugia, Orvieto, and Rome

Day 2 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Check out the top-rated church, Cathedral Of Santa Maria Del Fiore. Afterward, continue to Piazza Della Signoria, a public square every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Ponte Vecchio. This world-famous historical landmark is an essential stop. Following that, head to Uffizi Gallery, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, an impressive observation deck in the city.

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.

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

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.

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!

On day 3 of your road trip, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa and Lucca.

Visiting Piazza Del Duomo, Pisa is always a good idea. This globally renowned public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Pisa Cathedral, a must-see church 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 Leaning Tower Of Pisa. This wondrous monument offers an enriching experience. For a change of pace, head to Guinigi Tower, where you can take in history-steeped features. Conclude your self-guided sightseeing tour with a visit to Piazza Dell'anfiteatro. These sights offer a fulfilling end to a perfect day.

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

Florence 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 Florence.

Treat yourself to a delightful dinner at Ristorante Buca Mario, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Agricola Toscana? It's another excellent option with a diverse menu. Consider reserving a table at Eataly Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Siena and San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in San Gimignano, where you'll spend 2 nights.

Fortezza Medicea (siena) brings Florence's character to life. This stunning monument is a highlight of any visit in the city. Then, enjoy Piazza Del Campo, another awe-inspiring attraction that never fails to captivate visitors. Next, head over to Siena Cathedral, one of the city’s most popular attractions, known for its enchanting features.

If you’re looking for more, spend time soaking in the atmosphere of Porta San Giovanni. This picture-perfect monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Duomo, an often recommended public square, and take a stroll around the area.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in San Gimignano. San Gimignano offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

San Gimignano 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 San Gimignano.

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

On day 5 of your road trip, you’ll start and end your day in San Gimignano, where you have 1 night left to stay.

Castellina in Chianti is brimming with adventures.

Whatever your travel style is, Poggio Amorelli is an essential stop in San Gimignano. This curiosity-inducing winery provides an insightful glimpse into the village's identity. Next, discover Tumulo Di Montecalvario, a photogenic archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Rocca Di Castellina In Chianti, a beloved castle.

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

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

Relax and look forward to more memorable moments to come!

On day 6 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Santa Maria degli Angeli and Perugia are on today's agenda. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Basilica Of San Francesco D'assisi makes a great addition to your morning plans. This captivating church is a grand place to see in San Gimignano. Continue your discovery at Piazza Del Comune, an enchanting public square with stories to tell.

As you stroll around San Gimignano, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Basilica Di Santa Chiara. This intriguing church offers a picture-perfect encounter with San Gimignano. Next, make your way to Rocca Paolina to add another highlight to your day. After that, visit Piazza Iv Novembre, a beloved public square 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 San Gimignano.

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

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

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Perugia tonight.

After enjoying a fulfilling meal, continue your evening at Tommi Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Valentina offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffe Dal Perugino provides an excellent environment for a relaxed and enjoyable evening.

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

Your itinerary for day 7 of your road trip in Italy includes 2 stops and features some of the highlights of Orvieto and Bolsena. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 1 night.

Visiting Well Of St. Patrick is always a good idea. This notable monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Orvieto Cathedral, a must-see church in the village.

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 Torre Del Moro Orvieto. This curiosity-inducing monument offers an enriching experience. For a change of pace, head to Basilica Of Santa Cristina, Bolsena, where you can take in majestic features. These sights offer a fulfilling end to a perfect day.

At the end of the day, you will drive to Orvieto, 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 Orvieto. Enjoy a relaxing evening as you savor delicious local cuisine.

Unwind after your meal by stepping into Bar Duomo. This venue is celebrated for its extensive drink selections and cozy vibes.

Say good night to Orvieto and look forward to another great day of your road trip 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 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 2 nights.

Whatever your travel style is, Piazza Di Spagna is an essential stop in Orvieto. This wondrous public square provides an insightful glimpse into the city's identity. Next, discover Trevi Fountain, a history-steeped monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Navona, an iconic public square. When you’re done, don’t forget to make a stop at the globally renowned Pantheon.

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

Don’t miss out on dining at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

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

On day 9 of your road trip, you will have an entire day to discover what to see in Vatican City. You’ll stay in Rome for 1 night.

Vatican City is brimming with adventures. Trastevere is a neighborhood that stands out as one of the must-see places in Vatican City. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away. For another highlight, head to Monti, a neighborhood offering its own unique experiences.

St. Peter's Basilica is perfect for a self-paced visit during the day. Next on your list is Roman Forum, another must-visit landmark and globally renowned archeological site renowned for its picture-perfect 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 Colosseum. This historic archeological site is an essential place to visit for anyone looking for the full Rome experience.

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 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.

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

After enjoying a fulfilling meal, continue your evening at Sant' Eustachio Caffè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yellowsquare Rome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

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

On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Tivoli. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

Villa D'este is an ideal stop early in the day. This locally renowned palace is a must-visit in the town. When you’re ready for your next discovery, continue to Fontana Dell'organo, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Rome on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Fontana Dell'ovato (o Di Tivoli), an often recommended monument in the town. If you’re up for more discoveries, don’t forget to reserve some time for Villa Gregoriana.

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

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 Tijuana, a highly-rated dining destination in Florence. If you're eager to try something different, consider Djària - American Bar, another top spot with a tantalizing menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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