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

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Photo of the long staircase in the downtown of the beautiful ancient italian village.
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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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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Passetto
Arch of TrajanPorta PiaLazzaretto of AnconaState Tactile Museum Omero
Basilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioPalazzo Vecchiopiazza della Signoria
DavidGalleria dell'AccademiaCathedral of Santa Maria del FiorePalazzo Pittipiazzale MichelangeloOltrarno
Porta NuovaPiazza del Duomo, PisaLeaning Tower of PisaPiazza dell'AnfiteatroBasilica of San Domenico
Siena Cathedralpiazza del CampoTower of MangiaPubblico Palace

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Day 1

Day 1

  • Ancona - Arrival day
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  • Passetto
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Welcome to Ancona, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 2 nights immersing yourself in Ancona's charm before embarking on the next leg of your journey.

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 Passetto, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Ancona. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Treat yourself to a delicious dinner at Playa Solero, an excellent option for tonight's dining. Looking for something different? Zucchero a Velò offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Il Giardino. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Ancona.

Extend your evening after a delightful meal by visiting Posa Bar, which offers the perfect atmosphere for a night out. Moreover, Bar Four Roses is another popular option for a drink or two. Likewise, Amarillo Beer Bar Ancona also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 6 km, 51 min

  • Arch of Trajan
  • Porta Pia
  • Lazzaretto of Ancona
  • State Tactile Museum Omero
  • 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.

Start by visiting Arch Of Trajan, a prime spot to begin your journey. This culturally significant monument is sure to impress. Next on your list is Porta Pia, another must-visit landmark and underrated monument renowned for its respected features.

While exploring and sightseeing, take time to savor the culture of Ancona by sampling some local delicacies. When you’re ready for more sightseeing, head to Lazzaretto Of Ancona. This heritage-rich museum is an essential place to visit for anyone looking for the full Ancona experience. We also recommend visiting State Tactile Museum Omero, a locally appreciated museum.

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 lovely dining experience at Amarcord, a popular restaurant in Ancona. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Ancona at Bontà delle Marche, 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 Ristorante Pizzeria Da Romano. It’s yet another ideal choice to enhance your time in Ancona tonight.

Let the evening flow smoothly from dinner to drinks at Alla Tazza D'oro, a top-rated bar in the area.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 3

Day 3

  • Ancona
  • Florence
  • More

Drive 277 km, 3 hours 40 min

  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Palazzo Vecchio
  • piazza della Signoria
  • More

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Savor the day by visiting some of the best places to see in Ancona, including a church, an art gallery, a historical landmark, a palace, a public square and much more! Start your adventure at Basilica Of Santa Croce In Florence. This popular church is a must-visit for travelers looking for a unique holiday experience. Make your way to Uffizi Gallery located in Ancona for another exciting encounter.

Next, immerse yourself in the setting of Ponte Vecchio. Its awe-inspiring features will captivate you. After the historical landmark, continue your tour of the city with a visit to Palazzo Vecchio. Visitors usually appreciate the enchanting features of this palace. Next up is Piazza Della Signoria, a highly recommended public square.

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 an authentic adventure.

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.

Savor another day of unforgettable experiences in Italy!

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Day 4

Day 4

  • Florence
  • More

Drive 9 km, 1 hour 21 min

  • David
  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • Palazzo Pitti
  • piazzale Michelangelo
  • Oltrarno
  • 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.

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! David is the perfect place to start. This statue is one of the most well-known places to visit in Florence. Next, head to Galleria Dell'accademia, a captivating art gallery, known for its noteworthy 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 Cathedral Of Santa Maria Del Fiore. This grand church is a highly recommended experience. Nearby, you'll also find Pitti Palace and Piazzale Michelangelo. Visit these for an interesting touch to your journey.

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

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 5

Day 5

  • Florence
  • Siena
  • More

Drive 249 km, 3 hours 42 min

  • Porta Nuova
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Piazza dell'Anfiteatro
  • Basilica of San Domenico
  • More

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Pisa, Lucca, and Siena, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Siena. You’ll stay here for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Porta Nuova. This underrated monument provides an insightful glimpse into the city's identity. Next, discover Piazza Del Duomo, Pisa, a historic public square, promising a delightful encounter.

Continue your sightseeing with a visit to Leaning Tower Of Pisa, a wondrous monument. When you’re done, don’t forget to make a stop at the notable Piazza Dell'anfiteatro. Round off your day at Basilica Of San Domenico, another gem in Florence with culturally significant features to discover.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 6

Day 6

  • Siena
  • More

Drive 1.0 km, 16 min

  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Pubblico Palace
  • 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 well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Siena Cathedral is the first of them. Spend some time admiring this history-steeped church before continuing your journey. Piazza Del Campo is your next stop. This astonishing public square is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Tower Of Mangia. This picture-perfect monument is a sight to behold. To round off your sightseeing experience, visit Pubblico Palace.

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.

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

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.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink. Similarly, Bar Pinacoteca is well-suited for those looking to unwind in a social setting. San Paolo Pub is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 7

Day 7

  • Siena
  • Rome
  • More

Drive 242 km, 3 hours 37 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
  • More

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 2 nights here for some well-deserved relaxation.

Today’s itinerary in Siena covers several incredible sights, including an archeological site, a monument, and a public square. Start your adventure at Colosseum. This world-famous archeological site is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the UNESCO world heritage-designated wonders of Roman Forum, a must-see archeological site 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 Trevi Fountain. This globally renowned monument offers an enriching experience. For a change of pace, head to Pantheon, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to Piazza Navona. These sights offer a fulfilling end to a perfect day.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Rome. 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.

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.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 8

Day 8

  • Rome
  • More

Drive 16 km, 1 hour 34 min

  • Vatican Museums
  • Sistine Chapel
  • St Peter's Basilica
  • Castel Sant'Angelo
  • Piazza di Spagna
  • Spanish Steps
  • 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!

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Vatican Museums.

If you’re looking for more, spend time soaking in the atmosphere of Castel Sant'angelo. This symbolic castle is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Di Spagna, a world-famous 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.

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

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

Treat yourself to a delicious dinner at RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

After enjoying a fulfilling meal, continue your evening at Sant' Eustachio Caffè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yellowsquare Rome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

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

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Day 9

Day 9

  • Rome
  • Ancona
  • More

Drive 339 km, 5 hours

  • Basilica of San Francesco d'Assisi
  • National Archaeological Museum of Umbria
  • The Fontana Maggiore
  • Piazza IV Novembre
  • Perugia Cathedral
  • More

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Ancona, which will be your home away from home for 1 night.

Bring your curiosity for today’s adventure around Rome. Some of the town’s most loved attractions await! Basilica Of San Francesco D'assisi is the perfect place to start. This church is one of the most well-known places to visit in Rome. Next, head to National Archaeological Museum Of Umbria, an often recommended museum, known for its visually striking 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 The Fontana Maggiore. This culturally significant monument is a highly recommended experience. Nearby, you'll also find Piazza Iv Novembre and Perugia Cathedral. Visit these for an interesting touch to your journey.

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 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.

Enjoy a lovely meal at Pizzeria Pulcinella, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Donegal Irish Pub is another top choice with a popular menu. You could also check for a table at Vino E Cucina Miscia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Ancona tonight.

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

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Day 10

Day 10

  • Ancona - Departure day
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  • Piazza del Plebiscito
  • 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.

If you're up for some more sightseeing, we recommend visiting Piazza Del Plebiscito, an enchanting public square before you head out.

Make the most of your final day in Italy by visiting Ancona’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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

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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