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 remarkable 10-day road trip! Combine exploration with relaxation on a self-drive tour featuring Ancona, Florence, Siena, Rome, Perugia, and Santa Maria degli Angeli.

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. 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, 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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Day 1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
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Your road trip adventure in Italy begins as soon as you reach Ancona and pick up your car. You’ll stay here for 1 night and explore what to see in Ancona, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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.

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.

Enjoy a delicious meal 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.

If you’re not ready to end the night just yet, Posa Bar offers a perfect venue to relax and savor a drink. Similarly, Bar Four Roses is well-suited for those looking to unwind in a social setting. Amarillo Beer Bar Ancona is another excellent spot to enjoy a nightcap after a delightful meal.

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

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

Catch Ponte Vecchio before the crowds roll in. This romantic historical landmark is sure to ignite your curiosity. Next, dive into the romantic features of Uffizi Gallery, a must-visit art gallery 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 Palazzo Vecchio, an interesting palace. For a change of scene, check out Loggia Dei Lanzi, known for its romantic features. We also recommend visiting Piazza Della Signoria. This public square is a must for anyone looking to experience the city to the fullest.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour 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 Florence, it's often a good idea to reserve a table in advance.

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.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

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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

On day 3 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 1 night.

Whatever your travel style is, Piazzale Michelangelo is an essential stop in Florence. This top-rated observation deck provides an insightful glimpse into the city's identity. Next, discover Basilica Of Santa Croce In Florence, a photogenic church, promising a delightful encounter.

Continue your sightseeing with a visit to Giotto's Bell Tower, an underrated monument. When you’re done, don’t forget to make a stop at the spectacular Cathedral Of Santa Maria Del Fiore. Not far away from the church, you will find the photogenic Central Market, perfect for a quick visit. Round off your day at Galleria Dell'accademia, another gem in Florence with photogenic features to discover.

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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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.

Say good night to Florence and look forward to another great day of your road trip 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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Siena. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 1 night.

Experience Fortezza Medicea (siena), a worthwhile monument in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this symbolic church.

There are many interesting places to see in Florence, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most interesting majestic spots of interest. After exploring the church, visit the frequently visited Pubblico Palace. Not far away, you'll also find Piazza Del Campo. This public square is an UNESCO world heritage-listed highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Tower Of Mangia, a worthwhile monument in the city.

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

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

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass and celebrate another amazing day of your road trip 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

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.

Visiting Castel Sant'angelo is always a good idea. This extraordinary castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Campo De' Fiori, a must-see public square 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 Piazza Navona. This wondrous public square offers an enriching experience. For a change of pace, head to Pantheon, where you can take in photogenic features. Conclude your self-guided sightseeing tour with a visit to Altare Della Patria. These sights offer a fulfilling end to a perfect day.

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

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

Enjoy a delicious meal at La Bottega Roma, a highly-rated dining destination in Rome. If you're eager to try something different, consider Pasta In Corso, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s an excellent 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.

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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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 offers an itinerary packed with the best things to see in Rome. You’ll stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

No visit to Rome is complete without Colosseum. This wondrous archeological site is one of the top attractions in the city. Proceed to Roman Forum, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Trevi Fountain. This world-famous monument is a traveler-favorite. Not far away, you’ll find Piazza Di Spagna, another key site on your sightseeing itinerary. Spanish Steps is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Villa Borghese and uncover why it's recognized as one of the city's most spectacular attractions.

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

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

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.

Head back to your accommodation in Rome and get some rest to prepare for another magical day 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 of your road trip across Italy promises a magnificent time exploring what to see in Vatican City. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you decide to explore Vatican City on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. 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.

To truly experience Rome, make sure to drop by Vatican Museums. This world-famous art museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is St. Peter's Basilica, one of the city’s best highlights.

Next, check out Sistine Chapel, one of the most widely recognized places to see in Rome. This chapel is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Popolo. Wander around and soak in the enchanting atmosphere this public square offers.

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

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

Dine in style at Hotel de Russie, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna Italiana boasts a menu that's sure to impress. Also, be sure to check out The Parrot Bar. Known as a local hotspot, it’s a great choice for tonight in Rome.

Extend your evening after a delightful meal by visiting The Apartment Bar Roma, which offers the perfect atmosphere for a night out. Moreover, Hotel Hassler Roma is another popular option for a drink or two.

Raise your glass and celebrate another amazing day of your road trip 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 place, which are Perugia. At the end of the day, you will retreat to the hotel of your choice in Perugia, where will spend 1 night.

Make a stop at National Archaeological Museum Of Umbria. This worthwhile museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Rocca Paolina located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Carducci Gardens. Its visually striking features will captivate you. After the park, continue your tour of the city with a visit to Perugia Cathedral. Visitors usually appreciate the standout features of this church. Next up is Piazza Iv Novembre, a highly recommended public square. For a change of pace, head to The Fontana Maggiore. As one of the most up-and-coming attractions in Rome, this monument is the perfect place to end your self-guided sightseeing tour.

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

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

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

Explore the vibrant nightlife at Tommi Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Valentina for a great selection of flavorful drinks and a charming setting. Furthermore, Caffe Dal Perugino is perfect for those looking to extend their night with a touch of local flavor.

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

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Santa Maria degli Angeli. At the end of the day, enjoy the comforts of a top-rated hotel in Ancona, where you'll spend 1 night.

Make time for Basilica Of San Francesco D'assisi, a well-known church that is worthwhile a visit in the town. Nearby, you’ll find Portico Of Monte Frumentario, enchanting visitors with its culturally significant appeal. Continue your exploration at Roman Forum And Archaeological Museum. This archeological site is one of the town’s most underrated spots.

Enjoy the freedom of exploring Perugia 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 Del Comune. After exploring the public square, head to the locally appreciated Basilica Di Santa Chiara. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Rocca Maggiore, a place of romantic interest in Perugia.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Ancona. Ancona 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 Ancona's best restaurants.

Savor the flavors at Amarcord, a top pick for dinner tonight. Alternatively, Bontà delle Marche beckons with its unique menu offerings. Also, consider Ristorante Pizzeria Da Romano. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.

If you’re not ready to end the night just yet, Alla Tazza D'oro offers a perfect venue to relax and savor a drink.

Savor another day of unforgettable experiences in Italy!

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Day 10

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, we recommend visiting Cathedral Basilica Of St. Cyriacus, a breathtaking church before you head out.

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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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.
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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