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.

Brace yourself for today’s incredible lineup of attractions in Pisa, featuring fun adventures, scenic views, and picturesque spots. Start at Leaning Tower Of Pisa, a globally renowned monument in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this stunning public square.

There are many interesting places to see in Pisa, and when you are ready for more, go to Pisa Cathedral. This is one of the city’s most locally appreciated breathtaking spots of interest. After exploring the church, visit the famous Piazzale Michelangelo. Not far away, you'll also find Basilica Of Santa Croce In Florence. This church is a culturally significant highlight in Pisa.

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

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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

Get a good night's sleep and look forward to another great day on the road 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 Florence by discovering the best things there are to see and do in the city.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Ponte Vecchio is the first of them. Spend some time admiring this romantic historical landmark before continuing your journey. Uffizi Gallery is your next stop. This extraordinary art gallery is one of the best-rated sights in Florence.

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 Piazza Della Signoria. This majestic public square is a sight to behold. To round off your sightseeing experience, visit Cathedral Of Santa Maria Del Fiore and Galleria Dell'accademia. If time allows, end your day with Central Market, an eye-catching food market that offers a memorable conclusion to your exploration.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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.

A blend of family-friendly attractions, scenic views, and picturesque spots await you in Florence on today’s itinerary. First up is the often recommended 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 well-known 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 up-and-coming palace in the city. Finally, end your day with a visit to Porta Pispini, a culturally significant historical landmark that offers the perfect conclusion to your sightseeing of the day.

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

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Savor another day of unforgettable experiences in Italy!

On day 5 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience San Donato in Poggio and San Gimignano to the fullest today with this curated day itinerary!

Today, you'll explore some of the most beautiful places in Siena, including an astronomical observatory, a monument, an art gallery, a museum, a public square, a church and much more! Start your day with a visit to Osservatorio Polifunzionale Del Chianti. This up-and-coming astronomical observatory is a must-visit in the village. When you’re ready for your next discovery, continue to Porta San Giovanni, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Siena 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 Galleria Continua, a worthwhile art gallery in the village. If you’re up for more discoveries, don’t forget to reserve some time for Palazzo Comunale, Pinacoteca, Torre Grossa and Piazza Del Duomo. End your day with a visit to Chiesa Di Sant'agostino, an often recommended church that’s sure to leave a lasting impression.

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

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

Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Savor another day of unforgettable experiences in Italy!

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Rome, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Rome. You’ll stay here for 3 nights.

Start by visiting Castel Sant'angelo, a prime spot to begin your journey. This respected castle is sure to impress. Next on your list is Campo De' Fiori, another must-visit landmark and extraordinary public square renowned for its historic features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Navona. This enchanting public square is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Pantheon, a world-famous monument. Nearby, you'll also find Altare Della Patria, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Circus Maximus and wrap up your day with its breathtaking appeal.

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.

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.

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.

Following your dinner, dive into the local bar culture at La Botticella Of Poggi Giovanni. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Almalu Trastevere, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 7 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 2 nights and discover all the best things to see and do in the area.

Get ready for a day filled with fun adventures, scenic views, and picturesque spots in the charming city of Rome. Your adventure starts at Colosseum, a globally renowned local hot spot. Another notable attraction to explore is Roman Forum. This timeless archeological site is known for its picture-perfect appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Trevi Fountain. This history-steeped monument offers a fascinating experience that many visitors find memorable. Piazza Di Spagna is also worth visiting, along with Spanish Steps. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Villa Borghese. This spectacular park provides a fitting finale to your sightseeing.

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.

Enjoy a lovely dining experience at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

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

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

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights. You should also check out Via del Corso, a street offering more opportunities to enjoy the city’s vibrant atmosphere and landmarks.

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 astonishing 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.

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.

Following your dinner, dive into the local bar culture at The Apartment Bar Roma. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Hotel Hassler Roma, the perfect place for those looking to experience the best of the nightlife.

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

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Naples and Sorrento. At the end of the day, you will enjoy the comforts of a top-rated hotel in Sorrento, which will be your home away from home for 3 nights.

Today, you'll explore some of the most beautiful places in Rome, including a museum, a castle, a public square, a church and much more! Start your day with a visit to Naples National Archaeological Museum. This interesting museum is a must-visit in the city. When you’re ready for your next discovery, continue to Castel Nuovo, which may be one of the most respected places you will experience today.

One of the best things about exploring Rome on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza Del Plebiscito, an extraordinary public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for St. Francis Church And Convent.

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

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.

Dine in style at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top recommendation for dinner tonight. Or, for a change of pace, Bougainvillea boasts a menu that's sure to impress. Also, be sure to check out Banana Split. Known as a local hotspot, it’s a great choice for tonight in Sorrento.

Unwind after your meal by stepping into Leone Rosso Café. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Antiche Mura Sorrento offers a dynamic and energetic atmosphere for a glass or two.

Head back to your accommodation in Sorrento and get some rest in preparation for another magical 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 will return to Sorrento for your remaining 2 nights in the town 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 Positano, Amalfi, and Ravello.

Costiera Amalfitana Positano is must-visit beach and a great starting point for the day. Next, continue your journey to Amalfi Coast, an impressive coast, located just a leisurely stroll away. Next, head to Villa Rufolo, a romantic historical landmark, also available for your discovery today.

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

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

Enjoy a lovely meal at Fuoro51, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Hotel Bellevue Syrene is another top choice with a popular menu. You could also check for a table at Hotel Villa Fiorita. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Sorrento tonight.

Raise your glass to another unforgettable day in Italy!

On day 11 of your road trip, you’ll start and end your day in Sorrento, but spend part of the day exploring places of interest outside the immediate town. On today's itinerary, you'll find attractions in Pompei and Alberi. You still have 1 night left in Sorrento.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Sorrento allows for both. Start by heading to Archaeological Park Of Pompeii. This notable archeological site provides an insightful glimpse into the town's identity. Next, discover Basilica, an UNESCO world heritage-listed archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to View Of The Sorrento Peninsula, a frequently visited point of interest.

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

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

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

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

Bring your curiosity for today’s adventure around Sorrento. Some of the town’s most loved attractions await! Orvieto Cathedral is the perfect place to start. This church is one of the most captivating places to visit in Sorrento. Next, head to Orvieto Underground, a locally appreciated cave system, known for its photogenic 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 Torre Del Moro Orvieto. This picture-perfect monument is a highly recommended experience. Visit these for an interesting touch to your journey.

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

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Duomo, a well-loved spot among locals and tourists.

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

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Fortezza Medicea. This beloved castle is a visually striking place to see in Orvieto. Continue your discovery at Az. Agr. Crociani Susanna Crociani, an eye-catching winery with stories to tell.

As you stroll around Orvieto, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Antinori Nel Chianti Classico. This frequently visited winery offers an enchanting encounter with Orvieto. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Orvieto.

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

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.

Cap off your dinner by heading to Bar Mocambo, ideal for a leisurely evening with a drink in hand. Tree is another bar that offers an enjoyable setting. Similarly, Chupiteria is also a popular place to go on a night out, perfect for relaxing and socializing.

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