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

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Explore the best of Italy on a 9-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Loreto, Bologna, Pisa, Florence, Orvieto, and Rome. 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 2 nights in Ancona, 1 night in Bologna, 2 nights in Florence, and 3 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.

As you hit the open road and drive through Ancona, Loreto, Bologna, Pisa, Florence, Orvieto, and Rome, 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
Arch of Trajan
National Archaeological Museum of the MarchesCattedrale di San CiriacoSanctuary of the Holy House of Loreto
Two TowersPiazza MaggioreKnights' SquarePiazza del Duomo, PisaLeaning Tower of Pisa
Ponte VecchioUffizi Gallerypiazza della SignoriaBasilica of Santa Croce in Florencepiazzale Michelangelo
Cathedral of Santa Maria del FioreCentral MarketGalleria dell'AccademiaWell of St PatrickPonte Vecchio
Castel Sant'AngeloPiazza NavonaPantheonRoman ForumColosseumTrevi Fountain

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Day 1

Day 1

  • Ancona - Arrival day
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  • Arch of Trajan
  • More

Your road trip adventure in Italy begins as soon as you reach Ancona and pick up your car. You’ll stay in Ancona for 1 night 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 Arch Of Trajan or 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 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 delicious dinner at Playa Solero, an excellent option for tonight's dining. Looking for something different? Zucchero a Velò offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Il Giardino. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Ancona.

After savoring a delicious meal, step into the vibrant nightlife at Posa Bar, where the evening is just getting started. In the same way, Bar Four Roses offers a unique charm perfect for experiencing the local bar scene in Ancona. Amarillo Beer Bar Ancona is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day 2

Day 2

  • Ancona
  • Loreto
  • Bologna
  • More

Drive 275 km, 3 hours 28 min

  • National Archaeological Museum of the Marches
  • Cattedrale di San Ciriaco
  • Sanctuary of the Holy House of Loreto
  • More

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

Brace yourself for today’s incredible lineup of attractions in Ancona, featuring an instagrammable, a historically significant, a breathtaking, a profound, and a culturally significant. Start at Museo Archeologico Nazionale Delle Marche, a worthwhile museum in the city. Then, head to Cathedral Basilica Of St. Cyriacus and soak in the ambiance of this stunning church.

When you’re ready to jump back into the car and say goodbye to Ancona, you’ll hit the road in the direction of Loreto. This drive usually takes around 35 min. When you arrive, enjoy some sightseeing.

Take your self-guided tour to Sanctuary Of The Holy House Of Loreto, an interesting church that everyone visiting Loreto should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Begin your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at Bar Al Bricco D'oro, where the evening is just getting started. In the same way, Bar Freud E Squisito offers a unique charm perfect for experiencing the local bar scene in Bologna. Osteria Del Sole is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day 3

Day 3

  • Bologna
  • Pisa
  • Florence
  • More

Drive 279 km, 4 hours 9 min

  • Two Towers
  • Piazza Maggiore
  • Knights' Square
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Bologna and Pisa, 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 Florence. You’ll stay here for 2 nights.

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Two Towers. This breathtaking monument is sure to ignite your curiosity. Next, dive into the romantic features of Piazza Maggiore, a must-visit public square in the city.

Embrace the thrill of the open road as you wave goodbye to Bologna and set your GPS to Pisa. 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 2 hours 15 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Begin your journey at Knights' Square and explore the breathtaking features. Next, make your way to Piazza Del Duomo, Pisa, another highlight in the city. When you’re done exploring the public square, continue to Leaning Tower Of Pisa, a picture-perfect monument.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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.

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

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

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

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Day 4

Day 4

  • Florence
  • More

Drive 7 km, 52 min

  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • 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.

Today, you'll explore some of the most beautiful places in Florence, including a historical landmark, an art gallery, a public square, a church, an observation deck and much more! Start your day with a visit to Ponte Vecchio. This globally renowned historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Uffizi Gallery, which may be one of the most picture-perfect 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 Piazza Della Signoria, one of the city’s most extraordinary public square. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of Santa Croce In Florence and Piazzale Michelangelo.

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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

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Day 5

Day 5

  • Florence
  • Orvieto
  • Rome
  • More

Drive 296 km, 3 hours 55 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Galleria dell'Accademia
  • Well of St Patrick
  • Ponte Vecchio
  • 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 2 vibrant destinations - Florence and Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 3 nights here for some well-deserved relaxation.

A blend of a romantic, an enchanting, an eye-catching, a historic, a culturally significant, a symbolic, an UNESCO world heritage-listed, and a masterful await you in Florence on today’s itinerary. First up is the impressive church, Cathedral Of Santa Maria Del Fiore. It's a standout spot that offers a memorable visit. Afterward, continue to Central Market. A visit to this food market is an enriching experience for all.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Galleria Dell'accademia. This notable art gallery is an essential stop that should not be missed.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Orvieto. Expect your car journey to take a minimum of 1 hour 53 min. When you arrive in Orvieto, it's time to take a break from the road.

Well Of St. Patrick is a captivating monument we recommend making time to visit today. Discover its culturally significant features before continuing your self-guided tour.

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.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended restaurant in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition, known for its delicious mediterranean and creative menu.

Continue your evening by exploring the vibrant nightlife scene at La Botticella Of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Almalu Trastevere, a bar that offers unique local touches. Likewise, Bar Viminale Di Pepi Maurilio provides an excellent alternative for a fun evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 6

Day 6

  • Rome
  • More

Drive 7 km, 1 hour 10 min

  • Castel Sant'Angelo
  • Piazza Navona
  • Pantheon
  • Roman Forum
  • Colosseum
  • Trevi Fountain
  • More

Day 6 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Start by visiting Castel Sant'angelo, a prime spot to begin your journey. This history-steeped castle is sure to impress. Next on your list is Piazza Navona, another must-visit landmark and wondrous public square renowned for its noteworthy 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 Pantheon. This photogenic monument is a remarkable attraction that offers a unique experience. Roman Forum also adds charm to your journey, and Colosseum wraps up your day with its culturally significant appeal.

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

Treat yourself to a delicious dinner at RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 7

Day 7

  • Rome
  • More

Drive 9 km, 1 hour 6 min

  • Altare della Patria
  • Trevi Fountain
  • Piazza di Spagna
  • piazza del Popolo
  • Villa Borghese
  • More

On day 7 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring an enchanting, a photogenic, a historically significant, a symbolic, a noteworthy, a romantic, and a majestic. Start at Altare Della Patria, an interesting monument in the city. Then, head to Piazza Di Spagna and soak in the ambiance of this history-steeped public square.

There are many interesting places to see in Rome and when you are ready for more, go to Piazza Del Popolo. This is one of the city’s most astonishing spots. After exploring the public square, visit the extraordinary Villa Borghese.

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 Rome's best restaurants.

Enjoy a delicious meal at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue your lively evening at The Apartment Bar Roma, a perfect place for winding down or revving up the night, depending on which mood you’re in. Hotel Hassler Roma is another excellent bar that offers a great selection of drinks to suit any mood.

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
  • Ancona
  • More

Drive 312 km, 4 hours 2 min

  • St Peter's Basilica
  • Sistine Chapel
  • Vatican Museums
  • Trevi Fountain
  • More

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Ancona, where you’ll be staying for 1 night.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Vatican City, Vatican City. Your travel time is around 11 min.

Head to St. Peter's Basilica, a world-famous major basilica in Vatican City. This famous chapel is a top recommendation in the area. When you’re ready to explore more, Vatican Museums is an excellent choice.

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

Experience a symphony of flavors at Sot'Ajarchi in Ancona by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Sot'Ajarchi delights its guests with its exceptional variety of meals showcasing delicious seafood and from the marches cuisine. Or, if you're feeling adventurous, why not try Bontà delle Marche? It's another excellent option with a diverse menu.

Round off your dining experience by visiting Alla Tazza D'oro, a prime location for a drink.

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 9

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.

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.

Start your day with a visit to Parco Della Cittadella Di Ancona. This increasingly popular park is a must-visit in the city.

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

Dine in style at Pizzeria Pulcinella, a top recommendation for dinner tonight. Or, for a change of pace, Donegal Irish Pub boasts a menu that's sure to impress.

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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