14-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, Siena, Rome, Naples, and Amalfi

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

Knights' Square is perfect for a self-paced visit during the day. This historic public square is sure to impress. Next on your list is Leaning Tower Of Pisa, another must-visit landmark and iconic monument renowned for its noteworthy features.

While exploring and sightseeing, take time to savor the culture of Pisa by sampling some local delicacies. When you’re ready for more sightseeing, head to Pisa Cathedral. This majestic church is an essential place to visit for anyone looking for the full Pisa experience. We also recommend visiting Piazza Del Duomo, Pisa, a wondrous public square. Nearby, you'll also find Battistero Di San Giovanni, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Campo Santo and wrap up your day with its historic appeal.

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.

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

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

Day 3 offers an itinerary packed with the best things to see in Pisa. You’ll stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Cathedral Of Santa Maria Del Fiore leaves a lasting impression. This church is one of the most widely recognized places to visit in Florence. Next, head to Piazza Della Signoria, a famous 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 Palazzo Vecchio. This enchanting palace is a highly recommended experience. Nearby, you'll also find Ponte Vecchio and Uffizi Gallery Visit these for an interesting touch to your journey. Finish the day with a visit to Basilica Of Santa Croce In Florence, a culturally significant church in Florence.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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 delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

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

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

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 10 min.

When you're ready for some sights, head to Fortezza Medicea (siena), an up-and-coming monument in Siena. Explore its culturally significant features at your own pace before you continue your journey to your next attraction, Basilica Of San Domenico. This beloved church is a top recommendation in the area.

When you’re ready to explore more, Siena Cathedral is an excellent choice. Spend some time discovering what some claim to be the most history-steeped church in the region. Next, continue your sightseeing at the frequently visited Pubblico Palace and discover what makes this palace unique. If you’re up for one more stop in the city, head to Piazza Del Campo, an UNESCO world heritage-designated public square many travelers find the visit worthwhile.

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

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

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.

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.

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

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Siena, 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 San Gimignano.

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

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

Continue your road trip and head to your next destination, San Gimignano. This car ride takes around 50 min.

Set out on a self-guided sightseeing tour at Sangimignano1300 and explore the history-steeped features. Next, make your way to Palazzo Comunale, Pinacoteca, Torre Grossa, another highlight in San Gimignano. When you’re done exploring the museum, continue to Piazza Del Duomo, a symbolic public square.

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

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

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

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Relax and look forward to more memorable moments to come!

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.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Rome. 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 2 hours 38 min. Upon reaching Rome, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Villa Borghese is a famous park we recommend visiting today. Discover its romantic features before continuing your self-guided tour to Spanish Steps, a visually striking public square that’s well-regarded in the area.

Next, stop by Piazza Di Spagna, a romantic public square. While you’re nearby, don’t forget to visit Trevi Fountain, a history-steeped and truly unique monument. End your sightseeing at Pantheon, a globally renowned 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.

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.

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.

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.

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.

Day 8 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Rome.

To truly experience Rome, make sure to drop by 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 Altare Della Patria, one of the most popular 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, Campo De' Fiori. Wander around and soak in the romantic atmosphere this public square offers. Then, head to Piazza Navona, a top-rated public square that adds another dimension to your day. Finally, visit the famous Castel Sant'angelo, the last of our attraction recommendations for today.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine.

Have a fantastic dining experience at Hotel de Russie, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Taverna Italiana offers an enticing alternative with its varied menu. Additionally, The Parrot Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Naples. At the end of the day, enjoy the comforts of a top-rated hotel in Naples, where you'll spend 2 nights.

Naples’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 2 hours 30 min. Naples welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Spaccanapoli, an increasingly popular street that everyone visiting Naples should see. Next, head to Naples National Archaeological Museum. This photogenic museum is one of the most well-known attractions in the region.

If you're keen to see more, don’t miss out on Castel Sant'elmo, a breathtaking castle popular among locals as well as travelers. Piazza Del Plebiscito is an excellent attraction to visit next. Spend some time learning more about this extraordinary public square before you continue your journey.

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

Naples 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 Naples.

Enjoy a delicious meal at L'Oca Nera Irish Pub, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Mimì alla Ferrovia, another top spot with a mouthwatering menu. You might also want to secure a reservation at Spuzzulè Winebar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.

Let the evening flow smoothly from dinner to drinks at Happening Cocktail Bar, a top-rated bar in the area. For other recommendations, Shanti Art Musik Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Gran Caffè Gambrinus offers a memorable night with diverse drink options and excellent service.

Relax and look forward to more memorable moments to come!

Wake up to day 10 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Ottaviano, Ercolano, and Pompei. With 1 night to stay in Naples, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Set your GPS to Ottaviano and hit the road. Expect a journey of approximately 43 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Ottaviano beckons with new experiences!

Savor the day by heading to Mount Vesuvius, a locally appreciated volcano that draws visitors from near and far.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Ercolano. This drive usually takes around 26 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the city's best attractions, visit Archaeological Park Of Herculaneum, an often recommended archeological site that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

Pompei’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Ercolano behind. This drive usually takes around 18 min. Pompei welcomes you with a multitude of unique vacation experiences.

Our first attraction recommendation in Pompei is Archaeological Park Of Pompeii, a notable archeological site that draws attention for its UNESCO world heritage-listed features.

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

Naples 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 Naples.

Enjoy a delicious meal at Antica Pizzeria Di Matteo, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Mercure Napoli Centro Angioino, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Lazzara Trattoria e Pizzeria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.

Explore the vibrant nightlife at Archivio Storico - Cocktail Bar & Wonderfood after your meal, a hub for lively evenings and memorable moments. Or, head to Archeobar for a great selection of flavorful drinks and a charming setting. Furthermore, Babette Pub is perfect for those looking to extend their night with a touch of local flavor.

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

Dive into day 11 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Bomerano and Amalfi. At the end of the day, you’ll unwind at one of the finest accommodations in Amalfi, where you'll spend 2 nights.

When you’re ready to jump back into the car and say goodbye to Naples, you’ll hit the road in the direction of Bomerano. This drive usually takes around 1 hour 5 min.

Our first attraction recommendation in Bomerano is Li Cannati - Sentiero Degli Dei, a worthwhile hiking area that draws attention for its romantic features.

When you’re ready to jump back into the car and say goodbye to Bomerano, you’ll hit the road in the direction of Amalfi. This drive usually takes around 31 min.

Set out on a self-guided sightseeing tour at Antico Arsenale Della Repubblica Di Amalfi and explore the historic features. Next, make your way to Saint Andrew's Fountain Amalfi, another highlight in Amalfi.

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

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 Amalfi, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Pasticceria Pansa Amalfi, a highly-rated dining destination in Amalfi. If you're eager to try something different, consider Grand Hotel Excelsior Amalfi, another top spot with a tantalizing menu. You might also want to secure a reservation at Lido Azzurro. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Amalfi this evening.

After savoring a delicious meal, step into the vibrant nightlife at Bar Della Valle, where the evening is just getting started.

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

On day 12 of your road trip in Italy, you’ll start and end your day in Amalfi, but spend the day exploring what’s beyond the village. Since you still have 1 night to spend in Amalfi, there’s no need to rush. Experience Positano, Furore, Castiglione, and Ravello to the fullest today with this curated day itinerary.

When you’ve had your share of Amalfi, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Positano. Your travel time is around 47 min.

For a more meaningful self-guided tour of the village's best attractions, visit Costiera Amalfitana Positano, an up-and-coming beach that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’re ready to jump back into the car and say goodbye to Positano, you’ll hit the road in the direction of Furore. This drive usually takes around 26 min.

Set out on a self-guided sightseeing tour at Fiordo Di Furore and explore the eye-catching features.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Castiglione. This drive usually takes around 25 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 Villa Cimbrone Gardens, an increasingly popular botanical garden that everyone visiting Castiglione should see.

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

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

Enjoy a lovely meal at Ristorante Il Chiostro, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Gerry's pub is another top choice with a popular menu. You could also check for a table at Pizzeria Donna Stella. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Amalfi tonight.

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