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

On day 2 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Fasten your seatbelt and make your way to your next stop — Florence, home to many well-known sights in the region. Keep in mind that your travel time from Ancona to Florence may take around 3 hours 18 min without traffic disruptions. Upon arrival in Florence, we highly recommend checking out some of the top attractions.

Spend your afternoon discovering Piazzale Michelangelo, a spectacular observation deck known for its culturally significant features. Next, continue your sightseeing at Galleria Dell'accademia, a locally renowned art gallery.

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 Central Market and uncover the details of this eye-catching food market. Make sure to also explore Basilica Di Santa Maria Novella, Firenze (fi), a captivating 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.

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

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

On day 3 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 2 nights.

Start your day at Cathedral Of Santa Maria Del Fiore. This romantic church is a famous place to see in Florence. Then, wander over to Ponte Vecchio. If grand sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This picture-perfect art gallery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Palazzo Vecchio is a notable spot in the city that will captivate you with its unique charm. When you’re done at the palace, don’t forget to check out the grand Piazza Della Signoria. Take a moment to appreciate the fascinating details of this spectacular public square. Wrap up your self-guided tour of Florence's top attractions with a visit to Basilica Of Santa Croce 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.

Florence 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 Florence.

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.

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.

Savor another day of unforgettable experiences in Italy!

Greet day 4 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, 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 Pisa.

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 1 hour 16 min, without any stops or traffic disruptions.

Piazza Del Duomo, Pisa is a timeless public square we recommend visiting today. Discover its historic features before continuing your self-guided tour to Pisa Cathedral, a stunning church that’s well-regarded in the area.

While you’re nearby, don’t forget to visit Leaning Tower Of Pisa, a picture-perfect and truly unique monument.

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

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.

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

Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

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

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Bargino, Greve in Chianti, and San Regolo. With 1 night to stay in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Bargino is brimming with adventures.

Continue your road trip and head to your next destination, Bargino. This car ride takes around 40 min.

For a more meaningful self-guided tour of the village's best attractions, visit Antinori Nel Chianti Classico, a locally appreciated winery that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

Set your GPS to Greve in Chianti and hit the road. Expect a journey of approximately 28 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greve in Chianti beckons with new experiences!

One of our top recommendations for your sightseeing is Castle Of Verrazzano. Spend some time admiring the romantic features of the castle before you continue to your next stop.

Fasten your seatbelt and make your way to your next stop — San Regolo, home to many well-known sights in the region. Keep in mind that your travel time from Greve in Chianti to San Regolo may take around 59 min without traffic disruptions. Upon arrival in San Regolo, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Castello Di Brolio. Spend some time admiring the history-steeped features of the castle before you continue to your next stop.

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

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

Make sure to reserve a table at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo, 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 your meal, keep the night alive at a bar like Charlie Mixology Bar Di Aldinucci Riccardo, known for its lively atmosphere. Bar Pinacoteca is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, San Paolo Pub offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

Your itinerary for day 7 of your road trip in Italy includes 1 stop and features some of the highlights of Rome. At the end of the day, enjoy the comforts of a top-rated hotel in Rome, where you'll spend 3 nights.

Rome’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 2 hours 36 min. Rome welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Castel Sant'angelo, a widely recognized castle that draws visitors from near and far. When you're done, continue to Basilica Di Santa Maria Maggiore, where you can soak in the culturally significant surroundings.

Next, explore Trevi Fountain, yet another globally renowned place to see in the area. After the monument, make time to go to Pantheon. This culturally significant monument is well worth the visit. Lastly, head to Piazza Navona, an iconic public square you won’t want to miss.

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

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

Enjoy a delicious meal 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.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 8 of your road trip, you’ll start and end your day in Rome, where you have 2 nights left to stay.

Don’t miss Trastevere today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks. While you’re in the area, consider visiting Via del Corso, another street that adds to the charm of Vatican City.

Visiting Piazza Del Popolo is always a good idea. This famous public square is a place that is appreciated by travelers and locals alike.

Vatican City welcomes you with a multitude of unique vacation experiences.

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 globally renowned art museum that offers a unique experience.

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

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

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.

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.

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

Day 9 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.

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.

Colosseum brings Rome's character to life. This picture-perfect archeological site is a highlight of any visit in the city. Then, enjoy Arch Of Constantine, another masterful attraction that never fails to captivate visitors. Next, head over to Roman Forum, one of the city’s most globally renowned attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Capitoline Museums. This breathtaking museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Di Spagna, a wondrous public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Spanish Steps before you head back to your hotel.

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.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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.

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

Dive into day 10 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Alberi and Sorrento. At the end of the day, you’ll unwind at one of the finest accommodations in Sorrento, where you'll spend 2 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Alberi. This drive usually takes around 2 hours 56 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Belvedere Sorrento, an underrated observation deck in Alberi. Explore its awe-inspiring features at your own pace before you continue your journey.

Sorrento’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Alberi behind. This drive usually takes around 13 min. Sorrento welcomes you with a multitude of unique vacation experiences.

For a more meaningful self-guided tour of the village's best attractions, visit Museo Correale Di Terranova, a locally appreciated 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 Cathedral Of Saints Philip And James and admire its culturally significant features.

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.

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

Treat yourself to a wonderful meal at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top-rated dining spot in Sorrento. If you're in the mood for something new, try Bougainvillea, another premier location with a delectable menu. You might also want to book a table at Banana Split. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Sorrento.

Continue your evening by exploring the vibrant nightlife scene at Leone Rosso Café, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Antiche Mura Sorrento, a bar that offers unique local touches.

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

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

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.

Set out on a self-guided sightseeing tour at Costiera Amalfitana Positano and explore the mesmerizing features.

After soaking in Positano’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Ravello. Expect your car journey to take a minimum of 58 min. When you arrive in Ravello, it's time to take a break from the road.

Giardini Principessa Di Piemonte is a curiosity-inducing park we recommend visiting today. Discover its romantic features before continuing your self-guided tour to Villa Rufolo, a visually striking historical landmark that’s well-regarded in the area.

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 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 consistently gains high praises from customers, it’s an ideal choice in Sorrento tonight.

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

On day 12 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Perugia. When you’re not sightseeing, take time to relax at your chosen hotel in Perugia, where you’ll be staying for 2 nights.

When you’re ready to jump back into the car and say goodbye to Sorrento, you’ll hit the road in the direction of Perugia. This drive usually takes around 4 hours 38 min.

Our first attraction recommendation in Perugia is Etruscan Arch, an up-and-coming historical landmark that draws attention for its historic features. Spend some time soaking in the atmosphere before continuing to Perugia Cathedral, a culturally significant church that stands out in the 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 Piazza Iv Novembre, an increasingly popular public square that offers a unique experience. Be sure to also explore The Fontana Maggiore, a nearby monument, highly recommended by other travelers.

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

Perugia 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 Perugia.

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.

Round off your dining experience by visiting Tommi Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Valentina, a bar catering to every mood and preference. Caffe Dal Perugino likewise offers a unique atmosphere, perfect for a memorable night out.

Celebrate another amazing day of your road trip adventure 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.

Make time for Rocca Paolina, a frequently visited historical landmark that is worthwhile a visit in the city.

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

Spend your afternoon discovering Basilica Of San Francesco D'assisi, a captivating church known for its majestic features. Next, continue your sightseeing at Piazza Del Comune, an up-and-coming public square.

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 Basilica Di Santa Chiara and uncover the details of this breathtaking church. Make sure to also explore Rocca Maggiore, an often recommended castle.

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

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

Treat yourself to a delightful dinner at La Taverna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante del Sole? It's another excellent option with a diverse menu. Consider reserving a table at Al Mangiar Bene as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

Round off your dining experience by visiting Caffè Fortebraccio, a prime location for a drink. Alternatively, explore the distinctive characteristics of Caffe Del Banco, a bar catering to every mood and preference. Dempsey's Perugia likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

On day 14 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Recanati are on today's agenda. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

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

When you’ve had your share of Perugia, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Recanati. Your travel time is around 1 hour 55 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Villa Colloredo Mels Museum, an increasingly popular museum that everyone visiting Recanati should see. Next, head to Basilica Cattedrale Di San Flaviano. This culturally significant church is one of the most increasingly popular attractions in the region.

If you're keen to see more, don’t miss out on Leopardi's House, a visually striking museum popular among locals as well as travelers.

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

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.

After enjoying a fulfilling meal, continue your evening at Alla Tazza D'oro, ideal for those looking to unwind with a drink in a comfortable setting.

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