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

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

Enjoy all that Leaning Tower Of Pisa has to offer. This is an iconic monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a wondrous 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.

When you're ready for some sights, head to Piazzale Michelangelo, an impressive observation deck in Florence. Explore its respected features at your own pace before you continue your journey to your next attraction, Basilica Of Santa Croce In Florence. This notable church is a top recommendation in the area.

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

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

Head back to your accommodation in Florence and get some rest to prepare for another magical day of your road trip in Italy.

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

One of the most world-famous attractions included on the itinerary is Ponte Vecchio. This romantic historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Uffizi Gallery and learn what makes this romantic art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the impressive Piazza Della Signoria. After exploring the public square, head to Cathedral Of Santa Maria Del Fiore. This top-rated church is a highlight in Florence. As your day continues, stop by Galleria Dell'accademia, known for its detailed features. Lastly, don’t forget to check out the popular Central Market. Enjoy exploring this incredible food market at your own pace.

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 Florence's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Siena. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 2 nights.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 10 min.

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

If you're keen to see more, don’t miss out on Siena Cathedral, a visually striking 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 spectacular public square before you continue your journey. Lastly, visit Pubblico Palace, an UNESCO world heritage-designated palace and a top attraction in the city.

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.

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

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

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.

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

On day 5 of your road trip, you’ll start and end your day in Siena, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including San Donato in Poggio and San Gimignano.

Set your GPS to San Donato in Poggio and hit the road. Expect a journey of approximately 42 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Donato in Poggio beckons with new experiences!

One of our top recommendations for your sightseeing is Osservatorio Polifunzionale Del Chianti. Spend some time admiring the picture-perfect features of the astronomical observatory before you continue to your next stop.

After soaking in San Donato in Poggio’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: San Gimignano. Expect your car journey to take a minimum of 32 min. When you arrive in San Gimignano, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Porta San Giovanni. Spend some time admiring the historic features of the monument before you continue to your next stop. Then, head to Galleria Continua. This beloved art gallery is a traveler-favorite in the village.

If you're keen to see more, continue to Palazzo Comunale, Pinacoteca, Torre Grossa. Feed your curiosity by learning something new about the museum. Next, take your journey to Piazza Del Duomo, an underrated public square. Conclude your sightseeing at Chiesa Di Sant'agostino, known for its photogenic features.

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

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

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

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

Say good night to Siena and look forward to another great day of your road trip 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.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 2 hours 36 min, without any stops or traffic disruptions.

Castel Sant'angelo is a spectacular castle we recommend visiting today. Discover its symbolic features before continuing your self-guided tour to Campo De' Fiori, a historic public square that’s well-regarded in the area.

Next, stop by Piazza Navona, a history-steeped public square. While you’re nearby, don’t forget to visit Pantheon, a culturally significant and truly unique monument. End your sightseeing at Altare Della Patria, a captivating monument that’s highly recommended by travelers passing through the city.

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

Rome 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 Rome.

Make sure to reserve a table at La Bottega Roma, 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 Pasta In Corso, 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 Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

As the sun sets, rest up and recharge for the next leg 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 the city and use the provided itinerary to discover what to see in Rome.

Rome is brimming with adventures.

No visit to Rome is complete without Colosseum. This world-famous 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 famous 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.

Rome 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 Rome.

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

Raise your glass and celebrate another amazing day 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 still have 1 night to spend in Rome, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary.

At the top of the list of things to do today is to explore Trastevere, a neighborhood that captures the true essence of Vatican City. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions. Another must-visit is Via del Corso, a street offering a different perspective on Vatican City.

Piazza Del Popolo is perfect for a self-paced visit during the day. This history-steeped public square is sure to impress.

Admire the views and listen to some good music as you drive in the direction of Vatican 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 Vatican Museums, a wondrous art museum that offers a unique experience.

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.

Keep the evening going at The Apartment Bar Roma, a great choice for enjoying the after-dinner hours with a drink. You could also go to Hotel Hassler Roma, which offers a similarly pleasant setting and great drinks.

Relax and look forward to more memorable moments to come!

On day 9 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Naples and Sorrento are on today's agenda. In the evening, you’ll end up in Sorrento, where you will stay for 3 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Naples may take around 2 hours 27 min. Upon your arrival in Naples, you’ll be greeted with the opportunity to do some sightseeing and exploring.

For a more meaningful self-guided tour of the city's best attractions, visit Naples National Archaeological Museum, a locally renowned museum 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 Castel Nuovo and admire its culturally significant features.

When you’re ready, continue to Piazza Del Plebiscito, a widely recognized public square beloved by locals and tourists alike.

Fasten your seatbelt and make your way to your next stop — Sorrento, home to many well-known sights in the region. Keep in mind that your travel time from Naples to Sorrento may take around 10 min without traffic disruptions. Upon arrival in Sorrento, we highly recommend checking out some of the top attractions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to St. Francis Church And Convent, an often recommended church that everyone visiting Sorrento should see.

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

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 delightful dinner at Frankie's Pizza Bar Sorrento Brunch & Vegan, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bougainvillea? It's another excellent option with a diverse menu. Consider reserving a table at Banana Split as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Sorrento.

Continue your lively evening at Leone Rosso Café, a perfect place for winding down or revving up the night, depending on which mood you’re in. Hotel Antiche Mura Sorrento is another excellent bar that offers a great selection of drinks to suit any mood.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter 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.

After soaking in Sorrento’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Positano. Expect your car journey to take a minimum of 36 min. When you arrive in Positano, it's time to take a break from the road.

Spend your afternoon discovering Costiera Amalfitana Positano, a beloved beach known for its awe-inspiring features.

Amalfi’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Positano behind. This drive usually takes around 41 min. Amalfi welcomes you with a multitude of unique vacation experiences.

For a more meaningful self-guided tour of the village's best attractions, visit Amalfi Coast, a spectacular coast that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Ravello may take around 19 min. Upon your arrival in Ravello, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Set out on a self-guided sightseeing tour at Villa Rufolo and explore the romantic features.

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

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.

Don’t miss out on dining at Fuoro51, a top-rated dining destination in Sorrento. If you're in the mood to try something new, consider Hotel Bellevue Syrene, another top spot with a mouthwatering menu. You might also want to secure a reservation at Hotel Villa Fiorita. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Sorrento this evening.

Raise your glass to another unforgettable day in Italy!

On day 11 of your road trip, you'll get the chance to experience Pompei and Alberi. At the end of the day, you'll drive back to Sorrento, where you still have 1 night left to stay.

Whether you decide to explore Pompei on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pompei. This drive usually takes around 48 min, without any stops or traffic disruptions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Archaeological Park Of Pompeii, an interesting archeological site that everyone visiting Pompei should see. Next, head to Basilica. This symbolic archeological site is one of the most often recommended attractions in the region.

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

Sorrento 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 Sorrento.

Enjoy a delicious meal 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.

Your itinerary for day 12 of your road trip in Italy includes 1 stop and features some of the highlights of Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 2 nights.

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

Embrace the thrill of the open road as you wave goodbye to Sorrento and set your GPS to Orvieto. 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 3 hours 58 min. Upon reaching Orvieto, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Set out on a self-guided sightseeing tour at Orvieto Cathedral and explore the history-steeped features. Next, make your way to Orvieto Underground, another highlight in Orvieto. When you’re done exploring the cave system, continue to Torre Del Moro Orvieto, a picture-perfect monument.

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.

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

Unwind after your meal by stepping into Bar Duomo. This venue is celebrated for its extensive drink selections and cozy vibes.

Raise your glass to another unforgettable day in Italy!

Dive into day 14 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Montepulciano and Bargino. At the end of the day, you’ll unwind at one of the finest accommodations in Pisa, where you'll spend 1 night.

Continue your road trip and head to your next destination, Montepulciano. This car ride takes around 1 hour 3 min.

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

Bargino’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Montepulciano behind. This drive usually takes around 1 hour 29 min. Bargino welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Antinori Nel Chianti Classico and explore the romantic features.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.

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

Explore the vibrant nightlife at Bar Mocambo after your meal, a hub for lively evenings and memorable moments. Or, head to Tree for a great selection of flavorful drinks and a charming setting. Furthermore, Chupiteria is perfect for those looking to extend their night with a touch of local flavor.

Savor another day of unforgettable experiences in Italy!