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

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Explore the best of Italy on a 10-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Florence, Pisa, Lucca, Siena, Rome, Santa Maria degli Angeli, and Perugia. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

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

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

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

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

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

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

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

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

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Driver’s age is 30 - 65
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Itinerary summary

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

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Day 1

Day 1

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

Ancona is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Passetto, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Ancona. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in 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 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.

Cap off your dinner by heading to Posa Bar, ideal for a leisurely evening with a drink in hand. Bar Four Roses is another bar that offers an enjoyable setting. Similarly, Amarillo Beer Bar Ancona is also a popular place to go on a night out, perfect for relaxing and socializing.

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.

Immerse yourself in Ancona’s rich culture with today's sightseeing itinerary. Start your journey at Arch Of Trajan. This picture-perfect monument is sure to ignite your curiosity. Next, dive into the stunning features of Porta Pia, a must-visit monument 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 Lazzaretto Of Ancona, an increasingly popular museum. For a change of scene, check out State Tactile Museum Omero, known for its eye-catching features.

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 Ancona. 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.

Treat yourself to a wonderful meal at Amarcord, a top-rated dining spot in Ancona. If you're in the mood for something new, try Bontà delle Marche, another premier location with a delectable menu. You might also want to book a table at Ristorante Pizzeria Da Romano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Alla Tazza D'oro, a well-loved spot among locals and tourists.

Savor another day of unforgettable experiences 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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and history-rich sites. Whether you decide to explore Ancona on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Basilica Of Santa Croce In Florence is the first of them. Spend some time admiring this photogenic church before continuing your journey. Uffizi Gallery is your next stop. This widely recognized art gallery is one of the best-rated sights in Ancona.

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 Ponte Vecchio. This awe-inspiring historical landmark is a sight to behold. To round off your sightseeing experience, visit Palazzo Vecchio and Piazza Della Signoria.

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

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day in Italy!

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Day 4

Day 4

  • Florence
  • More

Drive 9 km, 1 hour 21 min

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

Day 4 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! David is the perfect place to start. This statue is one of the most locally renowned places to visit in Florence. Next, head to Galleria Dell'accademia, a notable art gallery, known for its noteworthy features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Cathedral Of Santa Maria Del Fiore. This UNESCO world heritage-designated church is a highly recommended experience. Nearby, you'll also find Pitti Palace and Piazzale Michelangelo. Visit these for an interesting touch to your journey.

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

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

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 5

Day 5

  • Florence
  • Siena
  • More

Drive 249 km, 3 hours 42 min

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Pisa, Lucca, and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Today’s route brings family-friendly attractions, picturesque spots, and historic treasures. The first attraction of today is Porta Nuova. This frequently visited monument is a heritage-rich place to see in Florence. Continue your discovery at Piazza Del Duomo, Pisa, a majestic public square with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Leaning Tower Of Pisa. This wondrous monument offers a culturally significant encounter with Florence. Next, make your way to Piazza Dell'anfiteatro to add another highlight to your day. After that, visit Basilica Of San Domenico, 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 Florence.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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

On day 6 of your road trip, you will have an entire day to explore Siena. You’ll stay in Siena for 1 night and discover all the best things to see and do in the area.

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

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

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Pinacoteca is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, San Paolo Pub ensures a night out tailored to your taste.

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

  • Siena
  • Rome
  • More

Drive 242 km, 3 hours 37 min

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 2 nights.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Colosseum is the perfect place to start. This archeological site is one of the most globally renowned places to visit in Siena. Next, head to Roman Forum, a globally renowned archeological site, 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 Trevi Fountain. This romantic monument is a highly recommended experience. Nearby, you'll also find Pantheon and Piazza Navona. Visit these for an interesting touch to your journey.

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 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.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

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 in Italy.

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Day 8

Day 8

  • Rome
  • More

Drive 16 km, 1 hour 34 min

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

On day 8 of your road trip in Italy, you’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 1 night more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Vatican Museums.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to St. Peter's Basilica. Next, make your way to Castel Sant'angelo to add another highlight to your day. After that, visit Piazza Di Spagna, an iconic public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Spanish Steps, an extraordinary public square in the city. 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.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

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 and reflect on the day's adventures.

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

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

Celebrate another amazing day of your road trip adventure 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

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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 Ancona. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, breathtaking views, and picturesque spots. Start at Basilica Of San Francesco D'assisi, a locally renowned church in the town. Then, head to National Archaeological Museum Of Umbria and soak in the ambiance of this visually striking museum.

There are many interesting places to see in Rome, and when you are ready for more, go to The Fontana Maggiore. This is one of the town’s most up-and-coming historic spots of interest. After exploring the monument, visit the often recommended Piazza Iv Novembre. Not far away, you'll also find Perugia Cathedral. This church is a culturally significant highlight in Rome.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. Check in and spend some time relaxing 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 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.

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

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Day 10

Day 10

  • Ancona - Departure day
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  • Piazza del Plebiscito
  • More

Day 10 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Ancona before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

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

On your last day in Italy, take time to indulge in shopping at Ancona’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

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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