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.

Immerse yourself in Pisa’s rich culture with today's sightseeing itinerary. Start your journey at Leaning Tower Of Pisa. This remarkable monument is sure to ignite your curiosity. Next, dive into the historic features of Piazza Del Duomo, Pisa, a must-visit public square 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 Pisa Cathedral, a beloved church. For a change of scene, check out Piazzale Michelangelo, known for its history-steeped features. We also recommend visiting Basilica Of Santa Croce In Florence. This church is a must for anyone looking to experience the city to the fullest.

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.

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.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass and celebrate another amazing day of your road trip 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.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the iconic Ponte Vecchio, a majestic historical landmark in Florence. Next, go to Uffizi Gallery.

After visiting Ponte Vecchio and Uffizi Gallery, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Della Signoria. This history-steeped public square offers a unique experience. Cathedral Of Santa Maria Del Fiore is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Galleria Dell'accademia, one of the most instagrammable places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Central Market.

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 Florence's best restaurants.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

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.

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This breathtaking monument is sure to impress. Next on your list is Fontebranda, another must-visit landmark and intriguing historical landmark renowned for its photogenic features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Siena Cathedral. This visually striking church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Piazza Del Campo, a widely recognized public square. Nearby, you'll also find Pubblico Palace, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Porta Pispini and wrap up your day with its historic appeal.

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

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable 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.

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

Set out on a day brimming with family-friendly attractions, scenic views, and photo-friendly spots. Start at the up-and-coming Osservatorio Polifunzionale Del Chianti, an eye-catching astronomical observatory in Siena. Next, go to Porta San Giovanni.

After visiting Osservatorio Polifunzionale Del Chianti and Porta San Giovanni, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Galleria Continua. This instagrammable art gallery offers a unique experience. Palazzo Comunale, Pinacoteca, Torre Grossa is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Del Duomo, one of the most enchanting places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by Chiesa Di Sant'agostino.

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

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

To truly maximize your evening out, consider visiting Charlie Mixology Bar Di Aldinucci Riccardo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Pinacoteca, another bar with an inviting ambiance. Similarly, San Paolo Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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.

Siena is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Castel Sant'angelo, an extraordinary castle that is worthwhile a visit in the city. Nearby, you’ll find Campo De' Fiori, enchanting visitors with its picture-perfect appeal. Continue your exploration at Piazza Navona. This public square is one of the city’s most iconic spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pantheon. After exploring the monument, head to the interesting Altare Della Patria. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Circus Maximus, a place of culturally significant interest in Siena.

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.

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

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

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

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

Day 7 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Colosseum. This globally renowned archeological site is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Roman Forum, one of the city’s best highlights.

Next, check out Trevi Fountain, one of the most world-famous places to see in Rome. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Di Spagna. Wander around and soak in the history-steeped atmosphere this public square offers. Then, head to Spanish Steps, a top-rated public square that adds another dimension to your day. Finally, visit the famous Villa Borghese, the last of our attraction recommendations for today.

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.

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.

Cap off your dinner by heading to Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

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’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 1 night more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

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. You can also explore Via del Corso, a street that offers a glimpse into local life and culture.

A blend of fun adventures, romantic experiences, and scenic views await you in Rome on today’s itinerary. First up is the globally renowned major basilica, St. Peter's Basilica. Afterward, continue to Sistine Chapel, a chapel 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 Vatican Museums. This globally renowned art museum is an essential stop. Following that, head to Piazza Del Popolo, another must-visit site that will enhance your experience.

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

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.

Treat yourself to a wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Cap off your dinner by heading to The Apartment Bar Roma, ideal for a leisurely evening with a drink in hand. Hotel Hassler Roma is another bar that offers an enjoyable setting.

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

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Naples and Sorrento. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Sorrento. You will spend 3 nights here for some well-deserved relaxation.

Savor the day by visiting some of the best places to see in Rome, including a museum, a castle, a public square, a church and much more! Start your adventure at Naples National Archaeological Museum. This popular museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Castel Nuovo located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Piazza Del Plebiscito. Its visually striking features will captivate you. After the public square, continue your tour of the city with a visit to St. Francis Church And Convent. Visitors usually appreciate the visually striking features of this church.

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 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 and reflect on the day's adventures.

Enjoy a lovely dining experience at Frankie's Pizza Bar Sorrento Brunch & Vegan, a popular restaurant in Sorrento. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Sorrento at Bougainvillea, 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 Banana Split. It’s yet another ideal choice to enhance your time in Sorrento tonight.

Continue the enjoyment post-dinner at Leone Rosso Café, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Antiche Mura Sorrento offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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

On day 10 of your road trip, you’ll start and end your day in Sorrento, where you'll stay for 2 nights more.

Start by visiting Costiera Amalfitana Positano, a prime spot to begin your journey. This peaceful beach is sure to impress.

While exploring and sightseeing, take time to savor the culture of Sorrento by sampling some local delicacies. When you’re ready for more sightseeing, head to Villa Rufolo. This visually striking historical landmark is an essential place to visit for anyone looking for the full Sorrento experience.

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.

Have a fantastic dining experience at Fuoro51, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Hotel Bellevue Syrene offers an enticing alternative with its varied menu. Additionally, Hotel Villa Fiorita is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Sorrento.

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

Wake up to day 11 of your extraordinary road trip in Italy. With 1 night left in Sorrento, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

Today's adventure in Sorrento promises more breathtaking discoveries and enriching experiences! Begin at Archaeological Park Of Pompeii. This stunning archeological site is a highlight of any visit in the town. Then, enjoy Basilica, another standout attraction that never fails to captivate visitors.

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

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 Fauno Bar, an excellent option for tonight's dining. Looking for something different? L'Antica Trattoria offers a tantalizing alternative with its diverse menu. And don’t miss Hotel Continental. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Sorrento.

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

Dive into day 12 of your remarkable road trip in Italy. Today you will explore Orvieto, 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 Orvieto. You’ll stay here for 2 nights.

Get ready for an exciting day in Sorrento. Today’s sightseeing agenda includes a church, a cave system, and a monument. Begin your adventure at Orvieto Cathedral. This is a locally renowned church you should not miss. Another must-see is Orvieto Underground, a frequently visited cave system in Sorrento.

When you’re ready for the next sight, head to Torre Del Moro Orvieto.

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 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.

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

Savor another day of unforgettable experiences 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.

Brace yourself for today’s incredible lineup of attractions in Orvieto, featuring fun adventures, romantic experiences, and scenic views. Start at Fortezza Medicea, a frequently visited castle in the town. Then, head to Az. Agr. Crociani Susanna Crociani and soak in the ambiance of this romantic winery.

There are many interesting places to see in Orvieto, and when you are ready for more, go to Antinori Nel Chianti Classico. This is one of the town’s most up-and-coming instagrammable spots of interest.

When you’re done exploring for the day, you’ll drive to your hotel in Pisa. 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 Pisa's best restaurants.

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

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

Raise your glass to another unforgettable day in Italy!