Two-Week Italy Self-Drive Road Trip With Itinerary from Perugia to Siena, Florence, Rome, and Orvieto and surrounding area

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

Immerse yourself in Perugia’s rich culture with today's sightseeing itinerary. Start your journey at Porta Marzia. This awe-inspiring monument is sure to ignite your curiosity. Next, dive into the instagrammable features of Rocca Paolina, a must-visit historical landmark in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to National Archaeological Museum Of Umbria, an increasingly popular museum.

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 you explore more of Perugia, 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.

Treat yourself to a delicious dinner at La Taverna, an excellent option for tonight's dining. Looking for something different? Ristorante del Sole offers a tantalizing alternative with its diverse menu. And don’t miss Al Mangiar Bene. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Caffè Fortebraccio, a well-loved spot among locals and tourists. Or, head to Caffe Del Banco. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Dempsey's Perugia, another top-rated place in the area.

Savor another day of unforgettable experiences in Italy!

On day 3 of your road trip, you’ll start and end your day in Perugia, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Santa Maria degli Angeli. You still have 1 night left in Perugia.

Prepare for a day full of fun adventures, natural wonders, and scenic views. When you’re ready, kick off your sightseeing adventure at Eremo Delle Carceri. This curiosity-inducing monastery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Rocca Maggiore, one of the town’s best highlights.

Next, check out Basilica Di Santa Chiara, one of the most locally appreciated places to see in Perugia. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Comune. Wander around and soak in the romantic atmosphere this public square offers. Then, head to Basilica Of San Francesco D'assisi, a top-rated church that adds another dimension to your day.

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

As you explore more of Perugia, 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.

Dine in style at Perugia Plaza Hotel, a top recommendation for dinner tonight. Or, for a change of pace, Elfo Pub Perugia boasts a menu that's sure to impress. Also, be sure to check out Sangallo Palace Hotel. Known as a local hotspot, it’s a great choice for tonight in Perugia.

Explore the vibrant nightlife at Il Birrino after your meal, a hub for lively evenings and memorable moments. Or, head to Quei Bravi Ragazzi for a great selection of flavorful drinks and a charming setting. Furthermore, Lo Chalet - Lounge Bar is perfect for those looking to extend their night with a touch of local flavor.

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

On day 4 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 Siena. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Today, you'll explore some of the most beautiful places in Perugia, including a palace, a monument, a public square, a church and much more! Start your day with a visit to Pubblico Palace. This often recommended palace is a must-visit in the city. When you’re ready for your next discovery, continue to Tower Of Mangia, which may be one of the most respected places you will experience today.

One of the best things about exploring Perugia 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 Piazza Del Campo, an astonishing public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Siena Cathedral.

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.

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.

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.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 5 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 Regolo and Castellina in Chianti to the fullest today with this curated day itinerary!

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Siena on today’s itinerary. First up is the frequently visited castle, Castello Di Brolio. Afterward, continue to Tumulo Di Montecalvario, an archeological site every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the hamlet. Next, make your way to Rocca Di Castellina In Chianti. This locally appreciated castle is an essential stop.

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

After enjoying a fulfilling meal, continue your evening at Charlie Mixology Bar Di Aldinucci Riccardo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Pinacoteca offers a welcoming atmosphere for easing into the nightlife. Similarly, San Paolo Pub 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.

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 - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 3 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Pitti Palace is the perfect place to start. This palace is one of the most well-known places to visit in Siena. Next, head to Ponte Vecchio, a timeless historical landmark, known for its visually striking 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 eye-catching art gallery is a highly recommended experience. Nearby, you'll also find Palazzo Vecchio and Piazza Della Signoria. Visit these for an interesting touch to your journey.

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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

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

Day 7 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazzale Michelangelo. This spectacular observation deck is a symbolic place to see in Florence. Continue your discovery at Basilica Of Santa Croce In Florence, a photogenic church with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Giotto's Bell Tower. This often recommended monument offers a visually striking encounter with Florence. Next, make your way to Cathedral Of Santa Maria Del Fiore to add another highlight to your day. After that, visit Galleria Dell'accademia, a captivating art gallery that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at David, a popular statue in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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.

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

Don’t miss out on dining 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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night 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 Pisa.

Florence is brimming with adventures. Today’s wonderful stops include a monument, a cemetery, and a public square. Begin your sightseeing adventure at the wondrous Leaning Tower Of Pisa and allow yourself time to explore. Just a short distance away you'll find your next stop, Campo Santo, a picture-perfect cemetery that draws visitors from far and near.

Continue your journey to Piazza Del Duomo, Pisa, one of the city’s most wondrous spots that you shouldn’t miss.

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

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

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Gosh*, known for its inviting atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another great option if you’re looking for a place to get the night started. Similarly, Quelo Bar provides a great setting to enjoy the night away.

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

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Rome, 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 Rome. You’ll stay here for 4 nights.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Castel Sant'angelo. This enchanting castle is sure to ignite your curiosity. Next, dive into the majestic features of Trevi Fountain, a must-visit monument in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Piazza Di Spagna, an iconic public square. For a change of scene, check out Spanish Steps, known for its history-steeped features. We also recommend visiting Villa Borghese. This park is a must for anyone looking to experience the city to the fullest.

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.

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

Enjoy a delicious meal 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.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

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

On day 10 of your road trip, you’ll start and end your day in Rome, where you'll stay for 3 nights more.

One of the most iconic places you can visit today in Vatican City 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.

Start your day at St. Peter's Basilica. Then, wander over to Sistine Chapel. Nearby, you’ll also find Saint Peter's Square.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Vatican Museums is an iconic spot in the city that will captivate you with its unique charm. When you’re done at the art museum, don’t forget to check out the detailed Piazza Del Popolo. Take a moment to appreciate the fascinating details of this impressive public square.

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.

Enjoy a lovely meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

To truly maximize your evening out, consider visiting Sant' Eustachio Caffè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yellowsquare Rome, another bar with an inviting ambiance. Similarly, Caffè Portofino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Savor another day of unforgettable experiences in Italy!

Day 11 of your road trip across Italy promises a magnificent time exploring Rome. You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

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 Rome. Next, go to Roman Forum.

After visiting Colosseum and Roman Forum, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Capitoline Museums. This breathtaking museum offers a unique experience. Altare Della Patria is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Pantheon, one of the most culturally significant places to visit in Rome. If you still have some time left for sightseeing, we also recommend stopping by Piazza Navona.

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.

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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

Embark on another extraordinary experience on day 13 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Orvieto, which will be your home away from home for 1 night.

Rome is brimming with adventures. Today’s wonderful stops include a monument, a church, a cave system, a cave and much more! Begin your sightseeing adventure at the notable Well Of St. Patrick and allow yourself time to explore. Just a short distance away you'll find your next stop, Orvieto Cathedral, a romantic church that draws visitors from far and near.

Continue your journey to Orvieto Underground, one of the village’s most beloved spots that you shouldn’t miss. Another great site to visit is the underrated Torre Del Moro Orvieto. When you're finished at the monument, Pozzo Della Cava awaits your visit. This cave is a photogenic highlight on today's itinerary.

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 dinnertime approaches, it's time to head out for a bite to eat in Orvieto. If you are looking to dine at a popular restaurant in the town, it's often a good idea to reserve a table in advance.

Extend your evening after a delightful meal by visiting Bar Duomo, which offers the perfect atmosphere for a night out.

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

On day 14 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Todi. When you’re not sightseeing, take time to relax at your selected hotel in Perugia, where you’ll be staying for 1 night.

Today’s agenda in Orvieto includes a church, a park, and a public square. Church Of Saint Mary Of Consolation is must-visit church and a great starting point for the day. Next, continue your journey to Giardini Oberdan, an underrated park, located just a leisurely stroll away. Next, head to Piazza Del Popolo, a romantic public square, also available for your discovery today.

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.

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

Enjoy a delicious meal at Alphaville, a highly-rated dining destination in Perugia. If you're eager to try something different, consider Osteria a Priori, another top spot with a tantalizing menu. You might also want to secure a reservation at La Bottega di Perugia. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Perugia this evening.

Continue the enjoyment post-dinner at Punto Di Vista, a cherished local gathering spot renowned for its welcoming atmosphere.

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