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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Escape the ordinary with this exciting 10-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. 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 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.

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, accommodations, 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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Pick-up: 10:00
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Day1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
  • More

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 discovering what to see in Ancona 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. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Ancona. Make yourself at home and unwind 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.

Savor the flavors at Playa Solero, a top pick for dinner tonight. Alternatively, Zucchero a Velò beckons with its unique menu offerings. Also, consider Ristorante Il Giardino. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.

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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Day2

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

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

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

Continue your road trip and head to your next destination, Florence. This car ride takes around 3 hours 24 min.

Set out on a self-guided sightseeing tour at Ponte Vecchio and explore the history-steeped features. Next, make your way to Uffizi Gallery, another highlight in Florence. When you’re done exploring the art gallery, continue to Palazzo Vecchio, a visually striking palace.

Nearby, you will also find Loggia Dei Lanzi. This frequently visited public square is a top place to see in the area. Lastly, head to Piazza Della Signoria, an enchanting public square that is perfect for some final exploring in the city.

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 a true cultural experience.

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

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day3

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

Check out the spectacular observation deck, Piazzale Michelangelo. Afterward, continue to Basilica Of Santa Croce In Florence, a church every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Giotto's Bell Tower. This up-and-coming monument is an essential stop. Following that, head to Cathedral Of Santa Maria Del Fiore, another must-visit site that will enhance your experience. Don’t forget to stop by Galleria Dell'accademia, a popular art gallery in the city. Finally, end your day with a visit to Central Market, a visually striking food market that offers the perfect conclusion to your sightseeing of the day.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

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

Raise your glass to another unforgettable day in Italy!

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Day4

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

On day 4 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 1 night.

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

Set your GPS to Siena and hit the road. Expect a journey of approximately 1 hour 10 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

Spend your afternoon discovering Fortezza Medicea (siena), a frequently visited monument known for its picture-perfect features. Next, continue your sightseeing at Basilica Of San Domenico, an increasingly popular church.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Siena Cathedral and uncover the details of this romantic church. Make sure to also explore Pubblico Palace, an intriguing palace. For your last stop, consider Piazza Del Campo, a romantic public square that many travelers find worth the detour.

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

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.

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. Known for great service, it’s a fantastic choice for tonight in Siena.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day5

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

Dive into day 5 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 2 hours 36 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the city's best attractions, visit Castel Sant'angelo, an impressive castle 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 Campo De' Fiori and admire its romantic features.

When you’re ready, continue to Piazza Navona, an iconic public square beloved by locals and tourists alike. Don't miss out on Pantheon, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Altare Della Patria, a remarkable place to see that you won’t regret spending some extra time discovering.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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

Don’t miss out on dining at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

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

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Day6

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 will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Rome.

Rome is brimming with adventures.

Make time for Colosseum, a world-famous archeological site that is worthwhile a visit in the city. Nearby, you’ll find Roman Forum, enchanting visitors with its awe-inspiring appeal. Continue your exploration at Trevi Fountain. This monument is one of the city’s most wondrous spots.

Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Di Spagna. After exploring the public square, head to the impressive Spanish Steps. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Villa Borghese, a place of idyllic interest in Rome.

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.

Rome 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 Rome.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Cap off your dinner by heading to Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day7

Day 7

  • Rome
  • More

Drive 15 km, 1 hour 5 min

  • piazza del Popolo
  • Monti
  • Via del Corso
  • More

On day 7 of your road trip, you will have an entire day to discover what to see in Vatican City. You’ll stay in Rome for 1 night.

At the top of the list of things to do today is to explore Monti, a neighborhood that captures the true essence of Vatican City. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions. Another must-visit is Via del Corso, a street offering a different perspective on Vatican City.

Piazza Del Popolo is an ideal stop early in the day. This astonishing public square is a must-visit in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

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

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Day8

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

Your itinerary for day 8 of your road trip in Italy includes 1 stop and features some of the highlights of Perugia. At the end of the day, enjoy the comforts of a top-rated hotel in Perugia, where you'll spend 1 night.

Fasten your seatbelt and make your way to your next stop — Perugia, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Perugia may take around 2 hours 13 min without traffic disruptions. Upon arrival in Perugia, we highly recommend checking out some of the top attractions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to National Archaeological Museum Of Umbria, a worthwhile museum that everyone visiting Perugia should see. Next, head to Rocca Paolina. This symbolic historical landmark is one of the most often recommended attractions in the region.

If you're keen to see more, don’t miss out on Carducci Gardens, a romantic park popular among locals as well as travelers. Perugia Cathedral is an excellent attraction to visit next. Spend some time learning more about this frequently visited church before you continue your journey. Lastly, visit Piazza Iv Novembre, a romantic public square and a top attraction in the city.

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

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

Enjoy a delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

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.

Savor another day of unforgettable experiences in Italy!

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Day9

Day 9

  • Perugia
  • Assisi
  • 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

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Santa Maria degli Angeli. At the end of the day, you will retreat to the hotel of your choice in Ancona, where will spend 1 night.

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 32 min. Upon your arrival in Santa Maria degli Angeli, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Our first attraction recommendation in Santa Maria degli Angeli is Basilica Of San Francesco D'assisi, a notable church that draws attention for its stunning features. Spend some time soaking in the atmosphere before continuing to Portico Of Monte Frumentario, a culturally significant historical landmark that stands out in the town.

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 Roman Forum And Archaeological Museum, an often recommended archeological site that offers a unique experience. Be sure to also explore Piazza Del Comune, a nearby public square, highly recommended by other travelers. End your self-guided tour at Basilica Di Santa Chiara, a stunning church and the perfect final attraction in Santa Maria degli Angeli.

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

Ancona 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 Ancona.

Enjoy a lovely meal at Amarcord, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Bontà delle Marche is another top choice with a popular menu. You could also check for a table at Ristorante Pizzeria Da Romano. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Ancona tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Alla Tazza D'oro, known for its inviting atmosphere.

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

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Day10

Day 10

  • Ancona - Departure day
  • More
  • 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 frequently visited church is a hotspot among locals.

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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Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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