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

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Photo of Bright summer view from flying drone of Cattedrale di San Ciriaco church and San Gregorio Illuminatore - Catholic church. Stunning morning cityscape of Ancona town, Italy, Europe.
Photo of the long staircase in the downtown of the beautiful ancient italian village.
9-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Rome, and Naples
9-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Rome, and Naples
9-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Rome, and Naples
9-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Rome, and Naples
9-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Rome, and Naples
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Escape the ordinary with this exciting 9-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Ancona, 3 nights in Florence, 2 nights in Rome, and 1 night in Naples. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

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

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

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Ancona, Florence, Pisa, Siena, San Gimignano, Rome, Naples, Pompei, Ravello, and Amalfi, 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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Day1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
  • 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 1 night 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 Piazza Del Plebiscito. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

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.

Don’t miss out on dining 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.

Unwind after your meal by stepping into Posa Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Four Roses offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Amarillo Beer Bar Ancona, another top-rated bar in the area.

Raise a toast to the start of your 9-day road trip in Italy!

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Day2

Day 2

  • Ancona
  • Florence
  • More

Drive 278 km, 3 hours 49 min

  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • More

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 3 nights.

When you’re ready to jump back into the car and say goodbye to Ancona, you’ll hit the road in the direction of Florence. This drive usually takes around 3 hours 21 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Basilica Of Santa Croce In Florence, an interesting church that everyone visiting Florence should see. Next, head to Uffizi Gallery. This picture-perfect art gallery is one of the most widely recognized attractions in the region.

If you're keen to see more, don’t miss out on Ponte Vecchio, a visually striking historical landmark popular among locals as well as travelers. Cathedral Of Santa Maria Del Fiore is an excellent attraction to visit next. Spend some time learning more about this famous church before you continue your journey. Lastly, visit Piazza Della Signoria, a history-steeped public square and a top attraction in the city.

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.

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

Enjoy a delicious meal at Ristorante Oliviero 1962, a 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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day3

Day 3

  • Florence
  • Pisa
  • More

Drive 197 km, 2 hours 59 min

  • Knights' Square
  • Leaning Tower of Pisa
  • Angelo Caduto
  • Pisa Cathedral
  • Campo santo
  • Piazza del Duomo, Pisa
  • More

On day 3 of your road trip, you’ll start and end your day in Florence, where you still have 2 nights left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 1 hour 17 min.

One of our top recommendations for your sightseeing is Knights' Square. Spend some time admiring the awe-inspiring features of the public square before you continue to your next stop. Then, head to Leaning Tower Of Pisa. This world-famous monument is a traveler-favorite in the city.

If you're keen to see more, continue to Angelo Caduto. Feed your curiosity by learning something new about the point of interest. Next, take your journey to Pisa Cathedral, an increasingly popular church. Conclude your sightseeing at Campo Santo, known for its UNESCO world heritage-listed features.

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

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Savor another day of unforgettable experiences in Italy!

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Day4

Day 4

  • Florence
  • Siena
  • San Gimignano
  • More

Drive 181 km, 3 hours 18 min

  • Pubblico Palace
  • Tower of Mangia
  • piazza del Campo
  • Siena Cathedral
  • Porta San Giovanni
  • Piazza del Duomo, San Gimignano
  • More

Wake up to day 4 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Siena and San Gimignano. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Siena’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 15 min. Siena welcomes you with a multitude of unique vacation experiences.

Spend your afternoon discovering Pubblico Palace, an often recommended palace known for its historic features. Next, continue your sightseeing at Tower Of Mangia, an intriguing monument.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Del Campo and uncover the details of this history-steeped public square. Make sure to also explore Siena Cathedral, a well-known church.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: San Gimignano. Expect your car journey to take a minimum of 42 min. When you arrive in San Gimignano, it's time to take a break from the road.

When you're ready for some sights, head to Porta San Giovanni, a curiosity-inducing monument in San Gimignano. Explore its picture-perfect features at your own pace before you continue your journey to your next attraction, Piazza Del Duomo. This intriguing public square is a top recommendation in the area.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

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.

Enjoy a lovely dining experience at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day5

Day 5

  • Florence
  • Rome
  • More

Drive 279 km, 4 hours 3 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
  • 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 1 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 2 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 3 hours 9 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Colosseum, an iconic archeological site in Rome. Explore its UNESCO world heritage-designated features at your own pace before you continue your journey to your next attraction, Roman Forum. This wondrous archeological site is a top recommendation in the area.

When you’re ready to explore more, Trevi Fountain is an excellent choice. Spend some time discovering what some claim to be the most romantic monument in the region. Next, continue your sightseeing at the iconic Pantheon and discover what makes this monument unique. If you’re up for one more stop in the city, head to Piazza Navona, a history-steeped public square many travelers find the visit worthwhile.

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

After a 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.

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

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

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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Day6

Day 6

  • Rome
  • Vatican City
  • More

Drive 17 km, 1 hour 44 min

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

On day 6 of your road trip, you’ll start and end your day in Rome, where you have 1 night left to stay.

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.

Castel Sant'angelo makes a great addition to your morning plans. This famous castle is a romantic place to see in Rome. Continue your discovery at Piazza Di Spagna, an enchanting public square with stories to tell.

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 Spanish Steps. This widely recognized public square offers an enchanting encounter with Rome. 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 in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Vatican City, Vatican City. Expect your car journey to take a minimum of 12 min. When you arrive in Vatican City, it's time to take a break from the road.

For a more meaningful self-guided tour of the city's best attractions, visit Vatican Museums, a timeless art museum that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’re ready, continue to Sistine Chapel, a top-rated chapel beloved by locals and tourists alike.

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

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

Don’t miss out on dining at 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.

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

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

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Day7

Day 7

  • Rome
  • Naples
  • Pompei
  • More

Drive 279 km, 3 hours 42 min

  • Naples National Archaeological Museum
  • piazza del Plebiscito
  • Archaeological Park of Pompeii
  • Basilica
  • More

Your itinerary for day 7 of your road trip in Italy includes 2 stops and features some of the highlights of Naples and Pompei. At the end of the day, enjoy the comforts of a top-rated hotel in Naples, where you'll spend 1 night.

Continue your road trip and head to your next destination, Naples. This car ride takes around 2 hours 27 min.

Spend your afternoon discovering Naples National Archaeological Museum, a well-known museum known for its photogenic features. Next, continue your sightseeing at Piazza Del Plebiscito, an astonishing public square.

Admire the views and listen to some good music as you drive in the direction of Pompei.

When you're ready for some sights, head to Archaeological Park Of Pompeii, a well-known archeological site in Pompei. Explore its breathtaking features at your own pace before you continue your journey to your next attraction, Basilica. This underrated archeological site is a top recommendation in the area.

At the end of the day, you will drive to Naples, 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 Naples's best restaurants.

Make sure to reserve a table at L'Oca Nera Irish Pub, an iconic dining spot in Naples. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Mimì alla Ferrovia, a popular restaurant in Naples. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Spuzzulè Winebar, a hidden gem nestled in Naples. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Happening Cocktail Bar, ideal for a leisurely evening with a drink in hand. Shanti Art Musik Bar is another bar that offers an enjoyable setting. Similarly, Gran Caffè Gambrinus is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day8

Day 8

  • Naples
  • Ravello
  • Amalfi
  • Ancona
  • More

Drive 534 km, 7 hours 19 min

  • Villa Rufolo
  • Amalfi Coast
  • Saint Andrew's Fountain Amalfi
  • More

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Ravello and Amalfi. At the end of the day, you’ll unwind at one of the finest accommodations in Ancona, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Naples and set your GPS to Ravello. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 10 min. Upon reaching Ravello, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Set out on a self-guided sightseeing tour at Villa Rufolo and explore the respected features.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Amalfi may take around 20 min. Upon your arrival in Amalfi, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Savor the day by heading to Amalfi Coast, a famous coast that draws visitors from near and far. When you're done, continue to Saint Andrew's Fountain Amalfi, where you can soak in the breathtaking surroundings.

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

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 Amarcord, a top recommendation for dinner tonight. Or, for a change of pace, Bontà delle Marche boasts a menu that's sure to impress. Also, be sure to check out Ristorante Pizzeria Da Romano. Known as a local hotspot, it’s a great choice for tonight in Ancona.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Alla Tazza D'oro stands out as an excellent choice for a post-dinner cocktail.

Savor another day of unforgettable experiences in Italy!

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Day9

Day 9

  • Ancona - Departure day
  • More
  • Parco Della Cittadella di Ancona
  • More

Day 9 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 Parco Della Cittadella Di Ancona. This intriguing park is a hotspot among locals.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Ancona.

If you're in the mood to try something new, consider Donegal Irish Pub, another top spot with a mouthwatering menu.

You’ll then say farewell to Ancona. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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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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