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!
Itinerary summary
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Day 1
- Ancona - Arrival day
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- Passetto
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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 in Ancona for 2 nights and explore the best things to see and do, 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 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.
Dine in style at Playa Solero, a top recommendation for dinner tonight. Or, for a change of pace, Zucchero a Velò boasts a menu that's sure to impress. Also, be sure to check out Ristorante Il Giardino. Known as a local hotspot, it’s a great choice for tonight in Ancona.
Following your dinner, dive into the local bar culture at Posa Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Four Roses, the perfect place for those looking to experience the best of the nightlife. Similarly, Amarillo Beer Bar Ancona provides excellent drinks and a great atmosphere, ensuring a memorable night out.
Raise a toast to the start of your 10-day road trip in Italy!
Day 2
- Ancona
- More
Drive 8 km, 54 min
- Grotta Azzurra Pathway
- State Tactile Museum Omero
- Lazzaretto of Ancona
- Arch of Trajan
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Day 2 of your road trip across Italy promises a magnificent time exploring Ancona. You have 1 night left in Ancona. Take the opportunity to experience more of the best attractions and activities in the city.
Get ready for a day filled with fun adventures, romantic experiences, and natural wonders in the charming city of Ancona. Your adventure starts at Grotta Azzurra Pathway, an intriguing local hot spot. Another notable attraction to explore is State Tactile Museum Omero. This frequently visited museum is known for its instagrammable 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 Lazzaretto Of Ancona. This symbolic museum offers a fascinating experience that many visitors find memorable. Arch Of Trajan is also worth visiting.
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.
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 gains consistently high praises from customers, it’s an ideal choice in Ancona tonight.
Continue the enjoyment post-dinner at Alla Tazza D'oro, a cherished local gathering spot renowned for its welcoming atmosphere.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 3
- Ancona
- Florence
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Drive 286 km, 3 hours 57 min
- The Boboli Gardens
- Palazzo Pitti
- Ponte Vecchio
- Uffizi Gallery
- Palazzo Vecchio
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On day 3 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.
Get ready to discover some of the most iconic wonders in Ancona, including a botanical garden, a palace, a historical landmark, an art gallery and much more! Start your day at The Boboli Gardens. This detailed botanical garden is a captivating place to see in Ancona. Then, wander over to Pitti Palace. If awe-inspiring sites excite you, this palace will be right up your alley. Nearby, you’ll also find Ponte Vecchio. This visually striking historical landmark is a favorite among visitors.
Ancona offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Uffizi Gallery is a widely recognized spot in the city that will captivate you with its unique charm. When you’re done at the art gallery, don’t forget to check out the visually striking Palazzo Vecchio. Take a moment to appreciate the fascinating details of this locally renowned palace in Ancona.
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.
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 Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.
Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.
Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!
Day 4
- Florence
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Drive 6 km, 1 hour 29 min
- piazzale Michelangelo
- Basilica of Santa Croce in Florence
- Monument to Dante Alighieri
- Cathedral of Santa Maria del Fiore
- Galleria dell'Accademia
- Central Market
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On day 4 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.
Today, you'll explore some of the most beautiful places in Florence, including an observation deck, a church, a monument, an art gallery, a food market and much more! Start your day with a visit to Piazzale Michelangelo. This top-rated observation deck is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of Santa Croce In Florence, which may be one of the most instagrammable places you will experience today.
One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Monument To Dante Alighieri, an underrated monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Cathedral Of Santa Maria Del Fiore and Galleria Dell'accademia.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.
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.
Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 5
- Florence
- Siena
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Drive 249 km, 3 hours 53 min
- Piazza del Duomo, Pisa
- Leaning Tower of Pisa
- Walls of Lucca
- Piazza dell'Anfiteatro
- Basilica of San Domenico
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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.
Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Florence. Begin your sightseeing with Piazza Del Duomo, Pisa. This wondrous public square is one of the top attractions in the city. Proceed to Leaning Tower Of Pisa, another must-visit attraction that enhances the city’s allure.
As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Mura Di Lucca. This underrated historical landmark is a traveler-favorite. Not far away, you’ll find Piazza Dell'anfiteatro, another key site on your sightseeing itinerary. Conclude your day at Basilica Of San Domenico and uncover why it's recognized as one of the city's most increasingly popular attractions.
When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and spend some time relaxing 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 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.
Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.
Say good night to Siena and look forward to another great day of your road trip in Italy!
Day 6
- Siena
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Drive 1.0 km, 16 min
- Siena Cathedral
- piazza del Campo
- Tower of Mangia
- Pubblico Palace
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Day 6 offers a multitude of experiences. You will stay in Siena for 1 night more, offering you enough time to explore at a relaxed pace.
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 extraordinary public square renowned for its visually striking features.
While exploring and sightseeing, take time to savor the ambiance of Siena by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Tower Of Mangia. This breathtaking monument is a remarkable attraction that offers a unique experience. Pubblico Palace also adds charm 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.
As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.
Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.
After enjoying a fulfilling meal, continue your evening at Charlie Mixology Bar Di Aldinucci Riccardo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Pinacoteca offers a welcoming atmosphere for easing into the nightlife. Similarly, San Paolo Pub provides an excellent environment for a relaxed and enjoyable evening.
Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip in Italy!
Day 7
- Siena
- Rome
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Drive 242 km, 3 hours 39 min
- Colosseum
- Roman Forum
- Trevi Fountain
- Piazza Navona
- Pantheon
- Capitoline Hill
- 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.
Get ready for a day filled with fun adventures, scenic views, and photo-friendly spots in the charming city of Siena. Your adventure starts at Colosseum, a globally renowned local hot spot. Another notable attraction to explore is Roman Forum. This iconic archeological site is known for its picture-perfect appeal.
After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Trevi Fountain. This history-steeped monument offers a fascinating experience that many visitors find memorable. Piazza Navona is also worth visiting, along with Pantheon. 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 Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
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.
Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic 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.
Relax and recharge in preparation for another adventurous day in Italy!
Day 8
- Rome
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Drive 17 km, 1 hour 39 min
- St Peter's Basilica
- Sistine Chapel
- Vatican Museums
- Castel Sant'Angelo
- piazza del Popolo
- Spanish Steps
- Trastevere
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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!
Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and take advantage of the nearby must-see sights located nearby.
Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at St. Peter's Basilica.
In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Vatican Museums, a timeless art museum. For a change of scene, check out Castel Sant'angelo, known for its romantic features.
When you’re done exploring for the day, you’ll return to Rome and your accommodation.
As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, 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 DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.
Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.
Raise your glass to another unforgettable day in Italy!
Day 9
- Rome
- Ancona
- More
Drive 339 km, 4 hours 59 min
- Basilica of San Francesco d'Assisi
- National Archaeological Museum of Umbria
- The Fontana Maggiore
- Perugia Cathedral
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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.
Start by visiting Basilica Of San Francesco D'assisi, a prime spot to begin your journey. This stunning church is sure to impress. Next on your list is National Archaeological Museum Of Umbria, another must-visit landmark and underrated museum renowned for its respected features.
While exploring and sightseeing, take time to savor the ambiance of Rome by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to The Fontana Maggiore. This historic monument is a remarkable attraction that offers a unique experience. Perugia Cathedral also adds charm to your journey.
At the end of the day, you will drive to Ancona, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.
After a day of adventure, treat yourself to an exquisite dinner at one of Ancona's best restaurants.
Savor the flavors at Pizzeria Pulcinella, a top pick for dinner tonight. Alternatively, Donegal Irish Pub beckons with its unique menu offerings. Also, consider Vino E Cucina Miscia. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.
Raise your glass to another unforgettable day in Italy!
Day 10
- Ancona - Departure day
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- Piazza del Plebiscito
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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, an enchanting public square before you head out.
Make the most of your final day in Italy by visiting Ancona’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Ancona.
Treat yourself to a delicious dinner at Mixer Bar, an excellent option for tonight's dining. Looking for something different? Osteria La Bottega Di Pinocchio offers a tantalizing alternative with its diverse menu. And don’t miss La Cantineta.
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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