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

On day 2 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 Pisa and Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Leaning Tower Of Pisa. This timeless monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Duomo, Pisa, one of the city’s best highlights.

Next, check out Pisa Cathedral, one of the most worthwhile places to see in Pisa. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazzale Michelangelo. Wander around and soak in the enchanting atmosphere this observation deck offers. Then, head to Basilica Of Santa Croce In Florence, a top-rated church that adds another dimension to your day.

At the end of the day, you will drive to Florence, 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal 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.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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

On day 3 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Ponte Vecchio is the perfect place to start. This historical landmark is one of the most wondrous places to visit in Florence. Next, head to Uffizi Gallery, an astonishing art gallery, known for its history-steeped 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 Piazza Della Signoria. This visually striking public square is a highly recommended experience. Nearby, you'll also find Cathedral Of Santa Maria Del Fiore and Galleria Dell'accademia. Visit these for an interesting touch to your journey. Finish the day with a visit to Central Market, an instagrammable food market 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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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.

Raise your glass and celebrate another amazing day 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.

A blend of family-friendly attractions, breathtaking views, and picturesque spots await you in Florence on today’s itinerary. First up is the locally appreciated monument, Fortezza Medicea (siena). Afterward, continue to Fontebranda, a historical landmark 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 Siena Cathedral. This notable church is an essential stop. Following that, head to Piazza Del Campo, another must-visit site that will enhance your experience. Don’t forget to stop by Pubblico Palace, an intriguing palace in the city. Finally, end your day with a visit to Porta Pispini, an awe-inspiring historical landmark that offers the perfect conclusion to your sightseeing of the day.

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.

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

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.

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.

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

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena 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 San Donato in Poggio and San Gimignano.

Get ready to discover some of the most iconic wonders in Siena, including an astronomical observatory, a monument, an art gallery, a museum, a public square, a church and much more! Start your day at Osservatorio Polifunzionale Del Chianti. This picture-perfect astronomical observatory is a frequently visited place to see in Siena. Then, wander over to Porta San Giovanni. If picture-perfect sites excite you, this monument will be right up your alley. Nearby, you’ll also find Galleria Continua. This instagrammable art gallery is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Palazzo Comunale, Pinacoteca, Torre Grossa is an increasingly popular spot in the village that will captivate you with its unique charm. When you’re done at the museum, don’t forget to check out the inviting Piazza Del Duomo. Take a moment to appreciate the fascinating details of this worthwhile public square. Wrap up your self-guided tour of Siena's top attractions with a visit to Chiesa Di Sant'agostino.

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.

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start. You could also check out Bar Pinacoteca, offering a different kind of charm. A last recommendation for the day is San Paolo Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Castel Sant'angelo is the perfect place to start. This castle is one of the most spectacular places to visit in Siena. Next, head to Campo De' Fiori, a top-rated public square, known for its romantic 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 Piazza Navona. This enchanting public square is a highly recommended experience. Nearby, you'll also find Pantheon and Altare Della Patria. Visit these for an interesting touch to your journey. Finish the day with a visit to Circus Maximus, a culturally significant archeological site in Siena.

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

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Round off your dining experience by visiting La Botticella Of Poggi Giovanni, a prime location for a drink. Alternatively, explore the distinctive characteristics of Almalu Trastevere, a bar catering to every mood and preference. Bar Viminale Di Pepi Maurilio likewise offers a unique atmosphere, perfect for a memorable night out.

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

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

Rome is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Colosseum, a wondrous archeological site that is worthwhile a visit in the city. Nearby, you’ll find Roman Forum, enchanting visitors with its picture-perfect appeal. Continue your exploration at Trevi Fountain. This monument is one of the city’s most timeless spots.

Enjoy the freedom of exploring Rome 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 Di Spagna. After exploring the public square, head to the spectacular Spanish Steps. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Villa Borghese, a place of eye-catching interest in Rome.

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

Make sure to reserve a table at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

At the end of the day, you'll drive back to Rome, where you'll stay for 1 night more.

A top thing to do today is to explore Trastevere, a must-see neighborhood in Vatican City. It's the perfect starting point for touring the top attractions in the area. You can also visit Via del Corso, an ideal street for continued sightseeing.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. St. Peter's Basilica is the first of them. Sistine Chapel is your next stop. This famous chapel is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Vatican Museums. To round off your sightseeing experience, visit Piazza Del Popolo.

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.

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

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

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Naples and Sorrento, 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 Sorrento. You’ll stay here for 3 nights.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Naples National Archaeological Museum. This instagrammable museum is a highlight of any visit in the city. Then, enjoy Castel Nuovo, another picture-perfect attraction that never fails to captivate visitors. Next, head over to Piazza Del Plebiscito, one of the city’s most famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of St. Francis Church And Convent. This enchanting church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

As you explore more of Sorrento, 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 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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Sorrento.

If you’re not ready to end the night just yet, Leone Rosso Café offers a perfect venue to relax and savor a drink. Similarly, Hotel Antiche Mura Sorrento is well-suited for those looking to unwind in a social setting.

Savor another day of unforgettable experiences in Italy!

Wake up to day 10 of your extraordinary road trip in Italy. With 2 nights left in Sorrento, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

Start your day with a visit to Costiera Amalfitana Positano. This beloved beach is a must-visit in the village.

One of the best things about exploring Sorrento 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 Villa Rufolo, an interesting historical landmark in the village.

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

As you explore more of Sorrento, 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 Fuoro51, a top-rated dining spot in Sorrento. If you're in the mood for something new, try Hotel Bellevue Syrene, another premier location with a delectable menu. You might also want to book a table at Hotel Villa Fiorita. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Sorrento.

Raise your glass to another unforgettable day in Italy!

On day 11 of your road trip in Italy, you’ll start and end your day in Sorrento, but spend the day exploring what’s beyond the town. Since you will return to Sorrento for 1 night more, there’s no need to rush. Experience Pompei and Alberi to the fullest today with this curated day itinerary!

Enjoy the perfect balance of relaxation and exploration in Sorrento today. One of the most locally renowned attractions included on the itinerary is Archaeological Park Of Pompeii. This historic archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica and learn what makes this UNESCO world heritage-listed archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile View Of The Sorrento Peninsula.

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

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

Enjoy a lovely meal at Fauno Bar, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, L'Antica Trattoria is another top choice with a popular menu. You could also check for a table at Hotel Continental. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Sorrento tonight.

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

Experience an unparalleled adventure on day 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Orvieto. You will spend 2 nights here for some well-deserved relaxation.

Today’s itinerary in Sorrento covers several incredible sights, including a church, a cave system, and a monument. Start your adventure at Orvieto Cathedral. This captivating church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the instagrammable wonders of Orvieto Underground, a must-see cave system in the town.

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 beloved monument offers an enriching experience. These sights offer a fulfilling end to a perfect day.

When you’re done exploring for the day, you’ll drive to your hotel in Orvieto. Check in and spend some time relaxing 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 an authentic adventure.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Duomo, known for its inviting atmosphere.

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

On day 14 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 Montepulciano and Bargino. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the locally appreciated Fortezza Medicea, a romantic castle in Orvieto. Next, go to Az. Agr. Crociani Susanna Crociani.

After visiting Fortezza Medicea and Az. Agr. Crociani Susanna Crociani, have a stroll along Orvieto's streets and take in the local charm. Continue your sightseeing by heading to Antinori Nel Chianti Classico. This romantic winery offers a unique experience.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Pisa. 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 meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

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

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