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

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

Enjoy all that Leaning Tower Of Pisa has to offer. This is a globally renowned monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a globally renowned public square in Pisa.

When you’re ready for the next sight, head to Pisa Cathedral.

Continue your road trip and head to your next destination, Florence. This car ride takes around 1 hour 16 min.

Spend your afternoon discovering Piazzale Michelangelo, an astonishing observation deck known for its history-steeped features. Next, continue your sightseeing at Basilica Of Santa Croce In Florence, a notable church.

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

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San 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.

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.

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

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Florence.

Florence is brimming with adventures.

Ponte Vecchio makes a great addition to your morning plans. This world-famous historical landmark is a romantic place to see in Florence. Continue your discovery at Uffizi Gallery, a standout art gallery 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 Piazza Della Signoria. This astonishing public square offers a history-steeped 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 Central Market, a captivating food market 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 experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

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.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 4 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Set your GPS to Siena and hit the road. Expect a journey of approximately 1 hour 10 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Fortezza Medicea (siena), an increasingly popular monument that everyone visiting Siena should see. Next, head to Fontebranda. This symbolic historical landmark is one of the most underrated attractions in the region.

If you're keen to see more, don’t miss out on Siena Cathedral, a majestic church popular among locals as well as travelers. Piazza Del Campo is an excellent attraction to visit next. Spend some time learning more about this top-rated public square before you continue your journey. Lastly, visit Pubblico Palace, a picture-perfect palace and a top attraction in the city.

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

Siena 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 Siena.

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.

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

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

San Donato in Poggio’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 42 min. San Donato in Poggio welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Osservatorio Polifunzionale Del Chianti, a frequently visited astronomical observatory in San Donato in Poggio. Explore its picture-perfect features at your own pace before you continue your journey.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Gimignano. This drive usually takes around 32 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the village's best attractions, visit Porta San Giovanni, a frequently visited monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Galleria Continua and admire its visually striking features.

When you’re ready, continue to Palazzo Comunale, Pinacoteca, Torre Grossa, an underrated museum beloved by locals and tourists alike. Don't miss out on Piazza Del Duomo, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Chiesa Di Sant'agostino, a culturally significant place to see that you won’t regret spending some extra time discovering.

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. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena. If you're in the mood for something new, try Fischi per Fiaschi, another premier location with a delectable menu. You might also want to book a table at Osteria da Divo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Charlie Mixology Bar Di Aldinucci Riccardo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Pinacoteca offers an ideal atmosphere to enjoy the pleasures of the night. San Paolo Pub is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day 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 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 3 nights.

Continue your road trip and head to your next destination, Rome. This car ride takes around 2 hours 36 min.

Our first attraction recommendation in Rome is Castel Sant'angelo, an astonishing castle that draws attention for its history-steeped features. Spend some time soaking in the atmosphere before continuing to Campo De' Fiori, a picture-perfect public square that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Piazza Navona, a globally renowned public square that offers a unique experience. Be sure to also explore Pantheon, a nearby monument, highly recommended by other travelers. End your self-guided tour at Altare Della Patria, a picture-perfect monument and the perfect final attraction in Rome.

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. If you are looking to dine at a popular restaurant in Rome, it's often a good idea to reserve a table in advance.

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.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 7 of your road trip across Italy promises a magnificent time exploring what to see in Rome. You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

No visit to Rome is complete without Colosseum. This globally renowned archeological site is one of the top attractions in the city. Proceed to Roman Forum, another must-visit attraction.

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 Trevi Fountain. This iconic monument is a traveler-favorite. Not far away, you’ll find Piazza Di Spagna, another key site on your sightseeing itinerary. Spanish Steps is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Villa Borghese and uncover why it's recognized as one of the city's most extraordinary attractions.

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.

Indulge in a memorable dining experience at one of Rome's most popular restaurants, and connect with friendly locals for a true cultural experience.

Treat yourself to a wonderful meal at RomAntica, a top-rated dining spot in Rome. If you're in the mood for something new, try Coso Ristorante, another premier location with a delectable menu. You might also want to book a table at DEROMA - Farine Romane. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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

On day 8 of your road trip, you'll get the chance to experience Vatican City and Rome. At the end of the day, you'll drive back to Rome, where you still have 1 night left to stay.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day. You might also want to visit Via del Corso, a street offering another perspective on the city.

Make time for Piazza Del Popolo, an impressive public square that is worthwhile a visit in the city.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Vatican City.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to St. Peter's Basilica, a timeless major basilica that everyone visiting Vatican City should see. Next, head to Sistine Chapel.

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

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.

Make sure to reserve a table at Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

To truly maximize your evening out, consider visiting The Apartment Bar Roma after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Hotel Hassler Roma, another bar with an inviting ambiance.

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

Dive into day 9 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Naples and Sorrento. At the end of the day, you’ll unwind at one of the finest accommodations in Sorrento, where you'll spend 3 nights.

Naples’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 2 hours 27 min. Naples welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Naples National Archaeological Museum, an interesting museum in Naples. Explore its respected features at your own pace before you continue your journey to your next attraction, Castel Nuovo. This popular castle is a top recommendation in the area.

When you’re ready to explore more, Piazza Del Plebiscito is an excellent choice. Spend some time discovering what some claim to be the most history-steeped public square in the region.

Embrace the thrill of the open road as you wave goodbye to Naples and set your GPS to Sorrento. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 10 min. Upon reaching Sorrento, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Savor the day by heading to St. Francis Church And Convent, a worthwhile church that draws visitors from near and far.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Sorrento. Sorrento 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 Sorrento. Enjoy a relaxing evening as you savor delicious local cuisine.

Treat yourself to a delicious dinner at Frankie's Pizza Bar Sorrento Brunch & Vegan, an excellent option for tonight's dining. Looking for something different? Bougainvillea offers a tantalizing alternative with its diverse menu. And don’t miss Banana Split. Known for great service, it’s a fantastic choice for tonight in Sorrento.

Following your dinner, dive into the local bar culture at Leone Rosso Café. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Hotel Antiche Mura Sorrento, the perfect place for those looking to experience the best of the nightlife.

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

Greet day 10 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 2 nights to stay in Sorrento, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Positano, Amalfi, and Ravello.

Positano is brimming with adventures.

Embrace the thrill of the open road as you wave goodbye to Sorrento and set your GPS to Positano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 36 min. Upon reaching Positano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Costiera Amalfitana Positano is an often recommended beach we recommend visiting today. Discover its mesmerizing features before continuing your self-guided tour.

After soaking in Positano’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Amalfi. Expect your car journey to take a minimum of 41 min. When you arrive in Amalfi, it's time to take a break from the road.

When you're ready for some sights, head to Amalfi Coast, a famous coast in Amalfi.

When you’re ready to jump back into the car and say goodbye to Amalfi, you’ll hit the road in the direction of Ravello. This drive usually takes around 19 min.

Our first attraction recommendation in Ravello is Villa Rufolo, a notable historical landmark that draws attention for its history-steeped features.

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

Indulge in a memorable dining experience at one of Sorrento's most popular restaurants, and connect with friendly locals for a true cultural experience.

Savor the flavors at Fuoro51, a top pick for dinner tonight. Alternatively, Hotel Bellevue Syrene beckons with its unique menu offerings. Also, consider Hotel Villa Fiorita. With its consistent customer satisfaction, it’s an excellent option for dining in Sorrento tonight.

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

Wake up to day 11 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pompei and Alberi. With 1 night to stay in Sorrento, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

When you’ve had your share of Sorrento, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pompei. Your travel time is around 48 min.

Savor the day by heading to Archaeological Park Of Pompeii, a notable archeological site that draws visitors from near and far. When you're done, continue to Basilica, where you can soak in the symbolic surroundings.

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

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

Don’t miss out on dining at Fauno Bar, a top-rated dining destination in Sorrento. If you're in the mood to try something new, consider L'Antica Trattoria, another top spot with a mouthwatering menu. You might also want to secure a reservation at Hotel Continental. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Sorrento this evening.

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

On day 12 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Orvieto. When you’re not sightseeing, take time to relax at your chosen hotel in Orvieto, where you’ll be staying for 2 nights.

Throughout the day, make sure to take breaks to appreciate the surroundings.

When you’re ready to jump back into the car and say goodbye to Sorrento, you’ll hit the road in the direction of Orvieto. This drive usually takes around 3 hours 58 min.

Orvieto Cathedral is a popular church we recommend visiting today. Discover its enchanting features before continuing your self-guided tour to Orvieto Underground, a heritage-rich cave system that’s well-regarded in the area.

Next, stop by Torre Del Moro Orvieto, a picture-perfect monument.

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

Indulge in a memorable dining experience at one of Orvieto's most popular restaurants, and connect with friendly locals for a true cultural experience.

If you’re not ready to end the night just yet, Bar Duomo offers a perfect venue to relax and savor a drink.

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

Your itinerary for day 14 of your road trip in Italy includes 2 stops and features some of the highlights of Montepulciano and Bargino. At the end of the day, enjoy the comforts of a top-rated hotel in Pisa, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Orvieto and set your GPS to Montepulciano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 3 min. Upon reaching Montepulciano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

One of our top recommendations for your sightseeing is Fortezza Medicea. Spend some time admiring the enchanting features of the castle before you continue to your next stop. Then, head to Az. Agr. Crociani Susanna Crociani. This increasingly popular winery is a traveler-favorite in the town.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Bargino may take around 1 hour 29 min. Upon your arrival in Bargino, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Antinori Nel Chianti Classico, a frequently visited winery that everyone visiting Bargino should see.

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

Enjoy a lovely dining experience at Ristorante Capodimonte Pisa, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at La Locanda Dei Pisani Doc Pisa, 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 Baribaldi Pisa. It’s yet another ideal choice to enhance your time in Pisa tonight.

Extend your evening after a delightful meal by visiting Bar Mocambo, which offers the perfect atmosphere for a night out. Moreover, Tree is another popular option for a drink or two. Likewise, Chupiteria also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!