Two-Week Italy Self-Drive Road Trip With Itinerary from Pisa traveling east to Florence, Siena, Perugia, Orvieto, Rome, and Naples

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and 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.

Pisa is home to plenty of attractions that offer fun adventures, scenic views, and photo-friendly spots! Start at Leaning Tower Of Pisa, a globally renowned monument that is worthwhile a visit in the city. Continue your exploration at Pisa Cathedral. This church is one of the city’s most underrated spots.

Enjoy the freedom of exploring Pisa at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Del Duomo, Pisa. After exploring the public square, head to the up-and-coming Campo Santo. This cemetery will wrap up today’s self-guided sightseeing tour in the city.

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.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await. The Boboli Gardens is the perfect place to start. This botanical garden is one of the most interesting places to visit in Florence. Next, head to Ponte Vecchio, a globally renowned historical landmark, known for its enchanting 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 offers a unique experience that is highly recommended. Meanwhile, Palazzo Vecchio adds its own distinct charm to your journey. Finish your day with a visit to Piazza Della Signoria, a history-steeped public square 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.

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 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.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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 exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Today, you'll explore some of the most beautiful places in Florence, including a church, a palace, a public square, a monument and much more! Start your day with a visit to Basilica Of San Domenico. This often recommended church is a must-visit in the city. When you’re ready for your next discovery, continue to Battistero Di San Giovanni Battista, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Florence 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 Siena Cathedral, a locally renowned church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pubblico Palace and Piazza Del Campo. End your day with a visit to Tower Of Mangia, a beloved monument that’s sure to leave a lasting impression.

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

As you explore more of Siena, 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 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.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. 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!

Wake up to day 5 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s itinerary in Siena covers several incredible sights, including a monument, a public square, a museum, a park and much more! Start your adventure at Porta San Giovanni. This worthwhile monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Piazza Del Duomo, a must-see public square 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 Palazzo Comunale, Pinacoteca, Torre Grossa. This locally appreciated museum offers an enriching experience. For a change of pace, head to Parco Della Rocca, where you can take in enchanting features.

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

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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Unwind after your meal by stepping into Charlie Mixology Bar Di Aldinucci Riccardo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Pinacoteca offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook San Paolo Pub, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli, 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 Perugia. You’ll stay here for 1 night.

Today’s agenda in Siena includes a church, a historical landmark, a public square, a castle and much more! Basilica Of San Francesco D'assisi is must-visit church and a great starting point for the day. Next, continue your journey to Portico Of Monte Frumentario, a curiosity-inducing historical landmark, located just a leisurely stroll away. Next, head to Church Of Santa Maria Sopra Minerva In Assisi, an awe-inspiring church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. If you’re looking for more, Piazza Del Comune is also an underrated attraction that is worthwhile a visit. Lastly, don’t miss Rocca Maggiore, a worthwhile gem to see in the town.

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

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

Make sure to reserve a table at Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Orvieto. You will spend 1 night here for some well-deserved relaxation.

Today's adventure in Perugia promises more breathtaking discoveries and enriching experiences! Begin at Piazza Iv Novembre. This romantic public square is a highlight of any visit in the city. Then, enjoy Perugia Cathedral, another culturally significant attraction that never fails to captivate visitors. Next, head over to Rocca Paolina, one of the city’s most increasingly popular attractions, known for its eye-catching features.

If you’re looking for more, spend time soaking in the atmosphere of National Archaeological Museum Of Umbria. This photogenic museum is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

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 and reflect on the day's adventures.

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

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 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 Orvieto. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Get ready to discover some of the most iconic wonders in Orvieto, including a monument, a church, a cave system, a cave and much more! Start your day at Torre Del Moro Orvieto. This picture-perfect monument is a frequently visited place to see in Orvieto. Then, wander over to Orvieto Cathedral. If visually striking sites excite you, this church will be right up your alley. Nearby, you’ll also find Orvieto Underground. This instagrammable cave system is a favorite among visitors.

Orvieto offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pozzo Della Cava is a frequently visited spot in the town that will captivate you with its unique charm.

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.

Enjoy a lovely dining experience at La Bottega Roma, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Pasta In Corso, 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 Trattoria Vecchia Roma. It’s yet another ideal choice to enhance your time in Rome tonight.

If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 9 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 Vatican City. You still have 2 nights left in Rome.

Don’t miss Trastevere in Rome today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the world-famous Piazza Navona, a romantic public square in Rome. Next, go to Castel Sant'angelo.

Sistine Chapel is another noteworthy stop.

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

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.

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.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 10 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.

Discover a day packed with fun adventures, breathtaking views, and photo-friendly spots in Rome. Begin your sightseeing with Colosseum. This wondrous archeological site is one of the top attractions in the city. Proceed to Roman Forum, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Pantheon. This world-famous monument is a traveler-favorite. Not far away, you’ll find Trevi Fountain, another key site on your sightseeing itinerary. Conclude your day at Piazza Di Spagna and uncover why it's recognized as one of the city's most timeless attractions.

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.

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 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

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

Embark on another extraordinary experience on day 11 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Naples. At the end of the day, you will enjoy the comforts of a top-rated hotel in Naples, which will be your home away from home for 3 nights.

A blend of fun adventures, romantic experiences, and scenic views await you in Rome on today’s itinerary. First up is the frequently visited street, Spaccanapoli. Afterward, continue to Cappella Sansevero, a museum every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Naples National Archaeological Museum. This popular museum is an essential stop. Following that, head to Castel Sant'elmo, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Plebiscito, a spectacular public square in the city.

At the end of the day, you will drive to Naples, 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 Naples's best restaurants.

Treat yourself to a delightful dinner at L'Oca Nera Irish Pub, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mimì alla Ferrovia? It's another excellent option with a diverse menu. Consider reserving a table at Spuzzulè Winebar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Naples.

Cap off your dinner by heading to Happening Cocktail Bar, ideal for a leisurely evening with a drink in hand. Shanti Art Musik Bar is another bar that offers an enjoyable setting. Similarly, Gran Caffè Gambrinus is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass to another unforgettable day in Italy!

Greet day 12 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Naples 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 Pompei.

Begin your adventure at Archaeological Park Of Pompeii. This is a popular archeological site you should not miss. Another must-see is Basilica, a beloved archeological site in Naples.

When you’re ready for the next sight, head to Temple Of Venus.

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

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

Enjoy a lovely dining experience at Antica Pizzeria Di Matteo, a popular restaurant in Naples. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Naples at Mercure Napoli Centro Angioino, 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 La Lazzara Trattoria e Pizzeria. It’s yet another ideal choice to enhance your time in Naples tonight.

Keep the excitement of the evening going by visiting a bar or two. Archivio Storico - Cocktail Bar & Wonderfood is an excellent place to start. You could also check out Archeobar, offering a different kind of charm. A last recommendation for the day is Babette Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 13 of your road trip, you’ll start and end your day in Naples, where you'll stay for 1 night more.

Start your adventure at Spiaggia Di Positano Marina Grande. This frequently visited beach is a must-visit for travelers looking for a unique holiday experience. Make your way to Amalfi Coast located in Naples for an enchanting atmosphere.

Next, immerse yourself in the setting of Villa Rufolo. Its history-steeped features will captivate you.

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

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

Enjoy a delicious meal at Opera Restaurant, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Trattoria San Ferdinando, another top spot with a mouthwatering menu. You might also want to secure a reservation at Anonymous Trattoria Gourmet. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.

Continue the enjoyment post-dinner at Gran Caffè Cimmino, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Flanagan's Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Napoli. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Today’s itinerary in Naples covers several incredible sights, including a monument, a public square, and a historical landmark. Start your adventure at Guinigi Tower. This worthwhile monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Piazza Dell'anfiteatro, a must-see public square 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 Clock Tower. This locally appreciated monument offers an enriching experience. For a change of pace, head to Mura Di Lucca, where you can take in romantic features.

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

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

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Locanda Dei Pisani Doc Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Baribaldi Pisa, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Bar Mocambo, a prime destination for a thrilling night out. Also, don’t forget to check out Tree, a bar that offers unique local touches. Likewise, Chupiteria provides an excellent alternative for a fun evening.

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