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

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Experience the freedom of the open road in Italy as you embark on an unforgettable 10-day road trip! This experience caters to every traveler, featuring destinations like Ancona, Florence, Pisa, Lucca, Siena, Rome, Santa Maria degli Angeli, and Perugia.

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

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

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

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

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

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

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

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

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
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
  • More

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

Ancona is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out 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.

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.

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

Today's adventure in Ancona promises more breathtaking discoveries and enriching experiences! Begin at Arch Of Trajan. This masterful monument is a highlight of any visit in the city. Then, enjoy Porta Pia, another culturally significant attraction that never fails to captivate visitors. Next, head over to Lazzaretto Of Ancona, one of the city’s most locally appreciated attractions, known for its photogenic features.

If you’re looking for more, spend time soaking in the atmosphere of State Tactile Museum Omero. This remarkable museum is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

As you explore more of Ancona, 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.

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.

Unwind after your meal by stepping into Alla Tazza D'oro. This venue is celebrated for its extensive drink selections and cozy vibes.

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

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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.

Get ready for a day filled with family-friendly attractions, photo-friendly spots, and historic treasures in the charming city of Ancona. Your adventure starts at Basilica Of Santa Croce In Florence, a notable local hot spot. Another notable attraction to explore is Uffizi Gallery. This famous art gallery is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Ancona's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Ponte Vecchio. This romantic historical landmark offers a fascinating experience that many visitors find memorable. Palazzo Vecchio is also worth visiting, along with Piazza Della Signoria. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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 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.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile 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 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 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

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

Set out on a day brimming with fun adventures, picturesque spots, and historic treasures. Next, go to Galleria Dell'accademia.

After visiting David and Galleria Dell'accademia, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Cathedral Of Santa Maria Del Fiore. This UNESCO world heritage-designated church offers a unique experience. Pitti Palace is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazzale Michelangelo, one of the most grand places to visit 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.

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

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences 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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 3 vibrant destinations - Pisa, Lucca, and Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Porta Nuova is the perfect place to start. This monument is one of the most increasingly popular places to visit in Florence. Next, head to Piazza Del Duomo, Pisa, a globally renowned public square, known for its picture-perfect 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 Leaning Tower Of Pisa. This masterful monument is a highly recommended experience. Nearby, you'll also find Piazza Dell'anfiteatro and Basilica Of San Domenico. Visit these for an interesting touch to your journey.

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

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

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

Day 6 of your road trip across Italy promises a magnificent time exploring Siena. You have 1 night left in Siena. Take the opportunity to experience more of the best attractions and activities in the city.

Start by visiting Siena Cathedral, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Piazza Del Campo, another must-visit landmark and impressive public square renowned for its respected features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Tower Of Mangia. This UNESCO world heritage-designated monument is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Pubblico Palace, a beloved 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.

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

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day 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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Rome, 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 Rome. You’ll stay here for 2 nights.

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 timeless archeological site is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant 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 timeless monument offers an enriching experience. For a change of pace, head to Pantheon, where you can take in heritage-rich 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 you explore more of Rome, 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.

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 enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Rome for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Vatican City and Rome.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Next, go to Sistine Chapel.

Castel Sant'angelo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Di Spagna, one of the most romantic places to visit in Rome. If you still have some time left for sightseeing, we also recommend stopping by Spanish Steps.

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.

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

Savor another day of unforgettable experiences 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.

Today’s route brings family-friendly attractions, breathtaking views, and photo-friendly spots. The first attraction of today is Basilica Of San Francesco D'assisi. This popular church is a picture-perfect place to see in Rome. Continue your discovery at National Archaeological Museum Of Umbria, a visually striking museum with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to The Fontana Maggiore. This curiosity-inducing monument offers a historic encounter with Rome. Next, make your way to Piazza Iv Novembre to add another highlight to your day. After that, visit Perugia Cathedral, a curiosity-inducing church that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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

Make sure to reserve a table at Pizzeria Pulcinella, 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 Donegal Irish Pub, 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 Vino E Cucina Miscia, a hidden gem nestled in Ancona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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Day 10

Day 10

  • Ancona - Departure day
  • More
  • 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, begin at Piazza Del Plebiscito. This frequently visited public square 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.

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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