Two-Week Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to Florence, Siena, Rome, Sorrento, and Perugia

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 3 nights.

Continue your road trip and head to your next destination, Florence. This car ride takes around 3 hours 18 min.

One of our top recommendations for your sightseeing is Piazzale Michelangelo. Spend some time admiring the romantic features of the observation deck before you continue to your next stop. Then, head to Galleria Dell'accademia. This locally renowned art gallery is a traveler-favorite in the city.

If you're keen to see more, continue to Central Market. Feed your curiosity by learning something new about the food market. Next, take your journey to Basilica Di Santa Maria Novella, Firenze (fi), an interesting church.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Florence.

Florence is brimming with adventures.

Visiting Cathedral Of Santa Maria Del Fiore is always a good idea. This astonishing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Ponte Vecchio, a must-see historical landmark in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Uffizi Gallery. This spectacular art gallery offers an enriching experience. For a change of pace, head to Palazzo Vecchio, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Piazza Della Signoria and Basilica Of Santa Croce In Florence These sights offer a fulfilling end to a perfect day.

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.

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 Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 4 of your road trip, you'll get the chance to experience Pisa. At the end of the day, you'll drive back to Florence, where you still have 1 night left to stay.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Pisa.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 1 hour 16 min. When you arrive in Pisa, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Piazza Del Duomo, Pisa and explore the UNESCO world heritage-listed features. Next, make your way to Pisa Cathedral, another highlight in Pisa.

Nearby, you will also find Leaning Tower Of Pisa. This timeless monument is a top place to see in the area.

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

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

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 6 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 still have 1 night to spend in Siena, there’s no need to rush. Experience Bargino, Greve in Chianti, and San Regolo to the fullest today with this curated day itinerary.

Fasten your seatbelt and make your way to your next stop — Bargino, home to many well-known sights in the region. Keep in mind that your travel time from Siena to Bargino may take around 40 min without traffic disruptions. Upon arrival in Bargino, 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 Antinori Nel Chianti Classico, an underrated winery that everyone visiting Bargino should see.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Greve in Chianti may take around 28 min. Upon your arrival in Greve in Chianti, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Set out on a self-guided sightseeing tour at Castle Of Verrazzano and explore the enchanting features.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Regolo. This drive usually takes around 59 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Castello Di Brolio, an up-and-coming castle in San Regolo. Explore its romantic features at your own pace before you continue your journey.

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

Siena 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 Siena.

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.

Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand. Bar Pinacoteca is another bar that offers an enjoyable setting. Similarly, San Paolo Pub is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Rome, where you’ll be staying for 3 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Rome may take around 2 hours 36 min. Upon your arrival in Rome, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Castel Sant'angelo, a spectacular castle known for its grand features. Next, continue your sightseeing at Basilica Di Santa Maria Maggiore, an interesting church.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Trevi Fountain and uncover the details of this enchanting monument. Make sure to also explore Pantheon, a timeless monument. For your last stop, consider Piazza Navona, a romantic public square that many travelers find worth the detour.

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

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

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.

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Almalu Trastevere is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Viminale Di Pepi Maurilio offers an excellent atmosphere for those looking to amp up the evening.

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

Wake up to day 8 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Vatican City and Rome. With 2 nights to stay in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Whether you decide to explore Vatican City on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Make sure to visit Trastevere, a popular neighborhood in Vatican City. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner. You can also explore Via del Corso today, a street that’s well worth a visit.

Whatever your travel style is, Piazza Del Popolo is an essential stop in Rome. This spectacular public square provides an insightful glimpse into the city's identity.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Vatican City.

Next, continue your sightseeing at Sistine Chapel, a famous chapel.

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

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

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 9 offers an itinerary packed with the best things to see in Ancona. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Whatever your travel style is, Colosseum is an essential stop in Rome. This globally renowned archeological site provides an insightful glimpse into the city's identity. Next, discover Arch Of Constantine, a historic monument, promising a delightful encounter.

Continue your sightseeing with a visit to Roman Forum, a world-famous archeological site. When you’re done, don’t forget to make a stop at the captivating Capitoline Museums. Not far away from the museum, you will find the romantic Spanish Steps, perfect for a quick visit. Round off your day at Piazza Di Spagna, another gem in Rome with history-steeped features to discover.

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

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. Known for great service, it’s a fantastic choice for tonight in Rome.

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.

Raise your glass to another unforgettable day in Italy!

On day 10 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Alberi and Sorrento are on today's agenda. In the evening, you’ll end up in Sorrento, where you will stay for 2 nights.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Alberi. 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 56 min. Upon reaching Alberi, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Belvedere Sorrento is an up-and-coming observation deck we recommend visiting today. Discover its gorgeous features before continuing your self-guided tour.

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 Alberi to Sorrento may take around 13 min without traffic disruptions. Upon arrival in Sorrento, we highly recommend checking out some of the top attractions.

Our first attraction recommendation in Sorrento is Museo Correale Di Terranova, an underrated museum that draws attention for its respected features. Spend some time soaking in the atmosphere before continuing to Cathedral Of Saints Philip And James, a culturally significant church that stands out in the village.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Sorrento. Sorrento offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Make sure to reserve a table at Frankie's Pizza Bar Sorrento Brunch & Vegan, an iconic dining spot in Sorrento. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bougainvillea, a popular restaurant in Sorrento. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Banana Split, a hidden gem nestled in Sorrento. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Leone Rosso Café, which offers the perfect atmosphere for a night out. Moreover, Hotel Antiche Mura Sorrento is another popular option for a drink or two.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 11 of your road trip, you’ll start and end your day in Sorrento, where you have 1 night left to stay.

Positano is brimming with adventures.

When you’re ready to jump back into the car and say goodbye to Sorrento, you’ll hit the road in the direction of Positano. This drive usually takes around 36 min.

For a more meaningful self-guided tour of the village's best attractions, visit Costiera Amalfitana Positano, an often recommended 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.

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

One of our top recommendations for your sightseeing is Giardini Principessa Di Piemonte. Spend some time admiring the gorgeous features of the park before you continue to your next stop. Then, head to Villa Rufolo. This popular historical landmark is a traveler-favorite in the village.

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

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.

Make sure to reserve a table at Fuoro51, an iconic dining spot in Sorrento. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Hotel Bellevue Syrene, a popular restaurant in Sorrento. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Hotel Villa Fiorita, a hidden gem nestled in Sorrento. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Raise your glass to another unforgettable day in Italy!

Dive into day 12 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Perugia. At the end of the day, you’ll unwind at one of the finest accommodations in Perugia, where you'll spend 2 nights.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the city.

After soaking in Sorrento’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Perugia. Expect your car journey to take a minimum of 4 hours 38 min. When you arrive in Perugia, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Etruscan Arch and explore the stunning features. Next, make your way to Perugia Cathedral, another highlight in Perugia. When you’re done exploring the church, continue to Piazza Iv Novembre, a symbolic public square.

Nearby, you will also find The Fontana Maggiore. This intriguing monument is a top place to see in the area.

At the end of the day, you will drive to Perugia, 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 Perugia's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a lovely dining experience at Ristorante Settimo Sigillo, a popular restaurant in Perugia. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Perugia at Caffè Baglioni, 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 Bar Pellas. It’s yet another ideal choice to enhance your time in Perugia tonight.

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

Raise your glass to another unforgettable day in Italy!

On day 13 of your road trip, you’ll start and end your day in Perugia, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Perugia and Santa Maria degli Angeli.

Awaiting your discovery is the beloved Rocca Paolina, a history-steeped historical landmark in Perugia.

When you’re ready to jump back into the car and say goodbye to Perugia, you’ll hit the road in the direction of Santa Maria degli Angeli. This drive usually takes around 28 min.

Basilica Of San Francesco D'assisi is a popular church we recommend visiting today. Discover its picture-perfect features before continuing your self-guided tour to Piazza Del Comune, an enchanting public square that’s well-regarded in the area.

Next, stop by Basilica Di Santa Chiara, a stunning church. While you’re nearby, don’t forget to visit Rocca Maggiore, a history-steeped and truly unique castle.

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

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

Treat yourself to a delicious dinner at La Taverna, an excellent option for tonight's dining. Looking for something different? Ristorante del Sole offers a tantalizing alternative with its diverse menu. And don’t miss Al Mangiar Bene. Known for great service, it’s a fantastic choice for tonight in Perugia.

Let the evening flow smoothly from dinner to drinks at Caffè Fortebraccio, a top-rated bar in the area. For other recommendations, Caffe Del Banco provides a perfect setting for rounding out your night with style and great drinks. Likewise, Dempsey's Perugia offers a memorable night with diverse drink options and excellent service.

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

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Recanati. At the end of the day, you will retreat to the hotel of your choice in Ancona, where will spend 1 night.

Fasten your seatbelt and make your way to your next stop — Recanati, home to many well-known sights in the region. Keep in mind that your travel time from Perugia to Recanati may take around 1 hour 55 min without traffic disruptions. Upon arrival in Recanati, we highly recommend checking out some of the top attractions.

Savor the day by heading to Villa Colloredo Mels Museum, a curiosity-inducing museum that draws visitors from near and far. When you're done, continue to Basilica Cattedrale Di San Flaviano, where you can soak in the heritage-rich surroundings.

Next, explore Leopardi's House, yet another worthwhile place to see in the area.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. 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 Ancona. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at Amarcord, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bontà delle Marche? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Pizzeria Da Romano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Ancona.

Cap off your dinner by heading to Alla Tazza D'oro, ideal for a leisurely evening with a drink in hand.

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.