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

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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, Siena, Rome, Perugia, and Santa Maria degli Angeli. 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 2 nights in Ancona, 2 nights in Florence, 1 night in Siena, 3 nights in Rome, and 1 night in Perugia. 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, Siena, Rome, Perugia, and Santa Maria degli Angeli, 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
Piazza del Plebiscito
Ponte VecchioUffizi GalleryPalazzo VecchioLoggia dei Lanzipiazza della Signoria
piazzale MichelangeloBasilica of Santa Croce in FlorenceGiotto's Bell TowerCathedral of Santa Maria del FioreGalleria dell'AccademiaCentral Market
Fortezza MediceaBasilica of San DomenicoSiena CathedralPubblico Palacepiazza del CampoTower of Mangia
Castel Sant'AngeloCampo de' FioriPiazza NavonaPantheonAltare della Patria
ColosseumRoman ForumTrevi FountainPiazza di SpagnaSpanish StepsVilla Borghese

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Day 1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
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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 1 night 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 Piazza Del Plebiscito, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Ancona. Make yourself at home and enjoy some downtime before heading 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 Ancona, it's often a good idea to reserve a table in advance.

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

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

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

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Day 2

Day 2

  • Ancona
  • Florence
  • More

Drive 285 km, 3 hours 35 min

  • Ponte Vecchio
  • Uffizi Gallery
  • Palazzo Vecchio
  • Loggia dei Lanzi
  • piazza della Signoria
  • More

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Savor the day by visiting some of the best places to see in Ancona, including a historical landmark, an art gallery, a palace, a public square and much more! Start your adventure at Ponte Vecchio. This wondrous historical landmark 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 Palazzo Vecchio. Its visually striking features will captivate you. After the palace, continue your tour of the city with a visit to Loggia Dei Lanzi. Visitors usually appreciate the romantic features of this public square. Next up is Piazza Della Signoria, a highly recommended public square.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence. 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 lovely dining experience at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

  • Florence
  • More

Drive 6 km, 1 hour 28 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Giotto's Bell Tower
  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • Central Market
  • More

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This enchanting observation deck is sure to ignite your curiosity. Next, dive into the culturally significant features of Basilica Of Santa Croce In Florence, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Giotto's Bell Tower, a curiosity-inducing monument. For a change of scene, check out Cathedral Of Santa Maria Del Fiore, known for its grand features. We also recommend visiting Galleria Dell'accademia. This art gallery is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Central Market, yet another locally renowned attraction in Florence.

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 Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. 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 Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 4

Day 4

  • Florence
  • Siena
  • More

Drive 77 km, 1 hour 45 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
  • Tower of Mangia
  • More

Dive into day 4 of your remarkable road trip in Italy. Today you will explore 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 1 night.

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This culturally significant monument is sure to impress. Next on your list is Basilica Of San Domenico, another must-visit landmark and curiosity-inducing church renowned for its respected features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Siena Cathedral. This romantic church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Pubblico Palace, an underrated palace. Nearby, you'll also find Piazza Del Campo, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Tower Of Mangia and wrap up your day with its culturally significant appeal.

At the end of the day, you will drive to Siena, 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 5

Day 5

  • Siena
  • Rome
  • More

Drive 234 km, 3 hours 24 min

  • Castel Sant'Angelo
  • Campo de' Fiori
  • Piazza Navona
  • Pantheon
  • Altare della Patria
  • More

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 3 nights.

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. Castel Sant'angelo is the first of them. Spend some time admiring this visually striking castle before continuing your journey. Campo De' Fiori is your next stop. This spectacular 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 Piazza Navona. This visually striking public square is a sight to behold. To round off your sightseeing experience, visit Pantheon and Altare Della Patria.

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

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

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.

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.

Savor another day of unforgettable experiences in Italy!

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Day 6

Day 6

  • Rome
  • More

Drive 10 km, 1 hour 21 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • Villa Borghese
  • More

Day 6 of your road trip across Italy promises a magnificent time exploring Rome. You have 2 nights left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Set out on a day brimming with fun adventures, breathtaking views, and photo-friendly spots. Start at the iconic Colosseum, an UNESCO world heritage-designated archeological site in Rome. Next, go to Roman Forum.

After visiting Colosseum and Roman Forum, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Trevi Fountain. This history-steeped monument offers a unique experience. Piazza Di Spagna is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Spanish Steps, one of the most history-steeped places to visit in Rome. If you still have some time left for sightseeing, we also recommend stopping by Villa Borghese.

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

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.

To truly maximize your evening out, consider visiting Sant' Eustachio Caffè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yellowsquare Rome, another bar with an inviting ambiance. Similarly, Caffè Portofino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 7

Day 7

  • Rome
  • More

Drive 15 km, 1 hour 5 min

  • Vatican Museums
  • St Peter's Basilica
  • Sistine Chapel
  • piazza del Popolo
  • Monti
  • Via del Corso
  • More

Day 7 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Make sure to visit Monti, 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.

Vatican Museums is must-visit art museum and a great starting point for the day. Next, continue your journey to St. Peter's Basilica, a wondrous major basilica, located just a leisurely stroll away.

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 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.

Enjoy a delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Let the evening flow smoothly from dinner to drinks at The Apartment Bar Roma, a top-rated bar in the area. For other recommendations, Hotel Hassler Roma provides a perfect setting for rounding out your night with style and great drinks.

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 8

Day 8

  • Rome
  • Perugia
  • More

Drive 175 km, 2 hours 36 min

  • National Archaeological Museum of Umbria
  • Rocca Paolina
  • Carducci Gardens
  • Perugia Cathedral
  • Piazza IV Novembre
  • The Fontana Maggiore
  • More

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

Today’s agenda in Rome includes a museum, a historical landmark, a park, a church, a public square, a monument and much more! National Archaeological Museum Of Umbria is must-visit museum and a great starting point for the day. Next, continue your journey to Rocca Paolina, a locally appreciated historical landmark, located just a leisurely stroll away. Next, head to Carducci Gardens, a visually striking park, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the curiosity-inducing Perugia Cathedral. If you’re looking for more, Piazza Iv Novembre is also a locally appreciated attraction that is worthwhile a visit. Lastly, don’t miss The Fontana Maggiore, a place of picture-perfect interest in the city.

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

As you explore more of Perugia, 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 Ristorante Settimo Sigillo, an excellent option for tonight's dining. Looking for something different? Caffè Baglioni offers a tantalizing alternative with its diverse menu. And don’t miss Bar Pellas. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

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

Raise your glass to another unforgettable day in Italy!

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Day 9

Day 9

  • Perugia
  • Ancona
  • More

Drive 157 km, 2 hours 55 min

  • Basilica of San Francesco d'Assisi
  • Portico of Monte Frumentario
  • Roman Forum and Archaeological Museum
  • Piazza del Comune
  • Basilica di Santa Chiara
  • Rocca Maggiore
  • 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. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Perugia is brimming with adventures. Today’s wonderful stops include a church, a historical landmark, an archeological site, a public square, a castle and much more! Begin your sightseeing adventure at the locally renowned Basilica Of San Francesco D'assisi and allow yourself time to explore. Just a short distance away you'll find your next stop, Portico Of Monte Frumentario, a breathtaking historical landmark that draws visitors from far and near.

Continue your journey to Roman Forum And Archaeological Museum, one of the town’s most worthwhile spots that you shouldn’t miss. Another great site to visit is the up-and-coming Piazza Del Comune. When you're finished at the public square, Basilica Di Santa Chiara awaits your visit. This church is a respected highlight on today's itinerary. Last up is a castle - the often recommended Rocca Maggiore.

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.

Make sure to reserve a table at Amarcord, an iconic dining spot in Ancona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bontà delle Marche, a popular restaurant in Ancona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Pizzeria Da Romano, a hidden gem nestled in Ancona. 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 Alla Tazza D'oro, a top-rated bar in the area.

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

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Day 10

Day 10

  • Ancona - Departure day
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  • Cattedrale di San Ciriaco
  • 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, begin at Cathedral Basilica Of St. Cyriacus. This worthwhile church is a popular place to see in the city.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Ancona's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

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

If you're in the mood to try something new, consider Donegal Irish Pub, another top spot with a mouthwatering 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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