10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to Florence, Siena, and Rome

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Explore the best of Italy on a 10-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Florence, Pisa, Lucca, Siena, Rome, Santa Maria degli Angeli, and Perugia. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Ancona, 2 nights in Florence, 2 nights in Siena, and 2 nights in Rome. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Ancona, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of St. Peter's Basilica.

As you hit the open road and drive through Ancona, Florence, Pisa, Lucca, Siena, Rome, Santa Maria degli Angeli, and Perugia, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Piazza del Plebiscito
Parco Belvedere PosatoraPassettoLazzaretto of AnconaCattedrale di San CiriacoLanterna rossa
Ponte VecchioUffizi Gallerypiazza della Signoria
Central MarketCathedral of Santa Maria del FioreGalleria dell'AccademiaDavidpiazzale Michelangelo
Campo santoPiazza del Duomo, PisaLeaning Tower of PisaPiazza dell'AnfiteatroFortezza Medicea
Porta Camollia, SienaPalazzo SalimbeniSiena Cathedralpiazza del CampoPorta Romana

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Day 1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
  • More

Say hello to Ancona! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Ancona for 2 nights before you continue your adventure!

Ancona is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Piazza Del Plebiscito or taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Ancona. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in 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 Ancona, it's often a good idea to reserve a table in advance.

Don’t miss out on dining at Playa Solero, a top-rated dining destination in Ancona. If you're in the mood to try something new, consider Zucchero a Velò, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Il Giardino. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Ancona this evening.

Following your dinner, dive into the local bar culture at Posa Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Four Roses, the perfect place for those looking to experience the best of the nightlife. Similarly, Amarillo Beer Bar Ancona provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise a toast to the start of your 10-day road trip in Italy!

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Day 2

Day 2

  • Ancona
  • More

Drive 20 km, 1 hour 40 min

  • Parco Belvedere Posatora
  • Passetto
  • Lazzaretto of Ancona
  • Cattedrale di San Ciriaco
  • Lanterna rossa
  • More

Day 2 offers a multitude of experiences. You will stay in Ancona for 1 night more, offering you enough time to explore at a relaxed pace.

Discover a day packed with family-friendly attractions, romantic experiences, and natural wonders in Ancona. Begin your sightseeing with Parco Belvedere Posatora. This often recommended park is one of the top attractions in the city. Proceed to Passetto, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Ancona, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Lazzaretto Of Ancona. This increasingly popular museum is a traveler-favorite. Not far away, you’ll find Cathedral Basilica Of St. Cyriacus, another key site on your sightseeing itinerary. Conclude your day at Lanterna Rossa and uncover why it's recognized as one of the city's most up-and-coming attractions.

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

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

Enjoy a delicious meal at Amarcord, a top-rated dining destination in Ancona. If you're in the mood to try something new, consider Bontà delle Marche, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Pizzeria Da Romano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Ancona this evening.

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

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

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Day 3

Day 3

  • Ancona
  • Florence
  • More

Drive 285 km, 3 hours 33 min

  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • More

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

When you arrive in Florence, it's time to take a break from the road.

Make your way to Ponte Vecchio, an iconic historical landmark that draws attention for its grand features. Spend some time soaking in the atmosphere before continuing to Uffizi Gallery, a romantic art gallery that stands out in the city. Next, visit Piazza Della Signoria, an impressive public square that offers a unique experience.

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.

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

Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 4

Day 4

  • Florence
  • More

Drive 11 km, 57 min

  • Central Market
  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • David
  • piazzale Michelangelo
  • More

Day 4 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Central Market. This well-known food market provides an insightful glimpse into the city's identity. Next, discover Cathedral Of Santa Maria Del Fiore, a romantic church, promising a delightful encounter.

Continue your sightseeing with a visit to Galleria Dell'accademia, a well-known art gallery. When you’re done, don’t forget to make a stop at the locally renowned David. Round off your day at Piazzale Michelangelo, another gem in Florence with enchanting features to discover.

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

After a 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.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!

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Day 5

Day 5

  • Florence
  • Pisa
  • Lucca
  • Siena
  • More

Drive 251 km, 3 hours 52 min

  • Campo santo
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Piazza dell'Anfiteatro
  • Fortezza Medicea
  • More

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Pisa, Lucca, and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Fasten your seatbelt and make your way to your next stop. Pisa, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Florence to Pisa may take around 1 hour 15 min without traffic disruptions. Upon arrival in Pisa, we highly recommend checking out some of the top attractions.

Take your self-guided tour to Campo Santo, an underrated cemetery that everyone visiting Pisa should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Next, head to Piazza Del Duomo, Pisa. This picture-perfect public square is one of the most globally renowned attractions in the region. Don’t miss out on Leaning Tower Of Pisa, a historic monument, popular among locals as well as travelers.

Set your GPS to Lucca and hit the road. Expect a journey of approximately 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Lucca beckons with new experiences!

Begin your journey at Piazza Dell'anfiteatro and explore the enchanting features.

When you’re ready to jump back into the car and say goodbye to Lucca, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 45 min. When you arrive, enjoy some sightseeing.

One of our top recommendations for your sightseeing is Fortezza Medicea (siena). Spend some time admiring the historic features of the monument before you continue to your next stop.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Siena. Siena offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 6

Day 6

  • Siena
  • More

Drive 4 km, 1 hour 9 min

  • Porta Camollia, Siena
  • Palazzo Salimbeni
  • Siena Cathedral
  • piazza del Campo
  • Porta Romana
  • More

On day 6 of your road trip, you will have an entire day to explore Siena. You’ll stay in Siena for 1 night and discover all the best things to see and do in the area.

Today’s itinerary in Siena covers several incredible sights, including a monument, a palace, a church, a public square and much more! Start your adventure at Porta Camollia, Siena. This locally appreciated monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the respected wonders of Palazzo Salimbeni, a must-see palace 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 Siena Cathedral. This well-known church offers an enriching experience. For a change of pace, head to Piazza Del Campo, where you can take in its UNESCO world heritage-designated features. Conclude your self-guided sightseeing tour with a visit to Porta Romana. This culturally significant monument offers a fulfilling end to a perfect day.

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

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

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

To truly maximize your evening out, consider visiting Charlie Mixology Bar Di Aldinucci Riccardo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Pinacoteca, another bar with an inviting ambiance. Similarly, San Paolo Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise your glass to another unforgettable day in Italy!

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Day 7

Day 7

  • Siena
  • Rome
  • More

Drive 234 km, 3 hours 27 min

  • piazza del Popolo
  • Piazza di Spagna
  • Trevi Fountain
  • Piazza Navona
  • Pantheon
  • More

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 2 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 38 min. Rome welcomes you with a multitude of unique vacation experiences.

Head to Piazza Del Popolo, a famous public square in Rome. Explore its romantic features at your own pace before you continue your journey to your next sight, Piazza Di Spagna. This timeless public square is a top recommendation in the area. When you’re ready to explore more, Trevi Fountain is an excellent choice. Spend some time discovering what some claim to be the most visually striking monument in the region. Next, continue your sightseeing at the world-famous Piazza Navona and discover what makes this public square unique. If you’re up for one more stop in the city, head to Pantheon, a culturally significant monument many travelers find worthwhile the visit.

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

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

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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 on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

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Day 8

Day 8

  • Rome
  • More

Drive 8 km, 45 min

  • St Peter's Basilica
  • Roman Forum
  • Colosseum
  • Trastevere
  • Via del Corso
  • More

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 will return to Rome for 1 night more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await. Roman Forum is the perfect place to start. This archeological site is one of the most world-famous places to visit in Rome. Next, head to Colosseum, a globally renowned archeological site, known for its picture-perfect features.

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

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

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.

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.

Savor another day of unforgettable experiences in Italy!

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Day 9

Day 9

  • Rome
  • Assisi
  • Perugia
  • Ancona
  • More

Drive 339 km, 4 hours 47 min

  • Basilica of San Francesco d'Assisi
  • National Gallery
  • Piazza IV Novembre
  • More

On day 9 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Continue your road trip and head to your next destination, Santa Maria degli Angeli. This car ride takes around 2 hours 25 min.

Spend your afternoon discovering Basilica Of San Francesco D'assisi, a notable church known for its stunning features.

After soaking in Santa Maria degli Angeli’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 29 min. When you arrive in Perugia, it's time to take a break from the road.

Head to National Gallery, an increasingly popular art gallery in Perugia. Explore its eye-catching features at your own pace before you continue your journey to your next sight, Piazza Iv Novembre. This locally appreciated public square is a top recommendation in the area.

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.

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

Enjoy a delicious meal at Pizzeria Pulcinella, a top-rated dining destination in Ancona. If you're in the mood to try something new, consider Donegal Irish Pub, another top spot with a mouthwatering menu. You might also want to secure a reservation at Vino E Cucina Miscia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Ancona this evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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Day 10

Day 10

  • Ancona - Departure day
  • More
  • Parco Della Cittadella di Ancona
  • More

Day 10 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Ancona before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Ancona on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Parco Della Cittadella Di Ancona is the first of them. Spend some time admiring this visually striking park before continuing your journey.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Ancona.

Have a fantastic dining experience at Mixer Bar, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria La Bottega Di Pinocchio offers an enticing alternative with its varied menu.

You’ll then say farewell to Ancona. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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