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

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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, Florence, Pisa, Siena, San Gimignano, Rome, Naples, Pompei, Ravello, and Amalfi. 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, 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 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, 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, 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
Piazza del Plebiscito
piazzale MichelangeloUffizi GalleryPonte VecchioCathedral of Santa Maria del Fiorepiazza della Signoria
Knights' SquareLeaning Tower of PisaAngelo CadutoPisa CathedralPiazza del Duomo, Pisa
Loggia del Papa, Sienapiazza del CampoBattistero di San Giovanni BattistaSiena CathedralPiazza del Duomo, San Gimignano
ColosseumRoman ForumTrevi FountainPiazza NavonaPantheon
St Peter's BasilicaPiazza di SpagnaTrastevereMontiVia del Corso

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Day 1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
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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 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 Piazza Del Plebiscito, 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.

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.

Explore the vibrant nightlife at Posa Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Four Roses for a great selection of flavorful drinks and a charming setting. Furthermore, Amarillo Beer Bar Ancona is perfect for those looking to extend their night with a touch of local flavor.

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

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Day 2

Day 2

  • Ancona
  • Florence
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Drive 279 km, 3 hours 58 min

  • piazzale Michelangelo
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • More

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 3 nights.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Piazzale Michelangelo. This extraordinary observation deck is a visually striking place to see in Ancona. Continue your discovery at Uffizi Gallery, a historic art gallery with stories to tell.

As you stroll around Ancona, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Ponte Vecchio. This timeless historical landmark offers a visually striking encounter with Ancona. Cathedral Of Santa Maria Del Fiore is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Ancona.

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

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

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

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

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Day 3

Day 3

  • Florence
  • More

Drive 197 km, 2 hours 57 min

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

At the end of the day, you'll drive back to Florence, where you'll stay for 2 nights more.

Start your day with a visit to Knights' Square. This locally appreciated public square is a must-visit in the city. When you’re ready for your next discovery, continue to Leaning Tower Of Pisa, which may be one of the most remarkable 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 Angelo Caduto, a frequently visited sightseeing destination in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pisa Cathedral and Piazza Del Duomo, Pisa.

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

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

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Day 4

Day 4

  • Florence
  • More

Drive 178 km, 3 hours 13 min

  • Loggia del Papa, Siena
  • piazza del Campo
  • Battistero di San Giovanni Battista
  • Siena Cathedral
  • Piazza del Duomo, San Gimignano
  • More

On day 4 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Loggia Del Papa, Siena. This frequently visited monument provides an insightful glimpse into the city's identity. Next, discover Piazza Del Campo, an enchanting public square, promising a delightful encounter.

Continue your sightseeing with a visit to Battistero Di San Giovanni Battista, an often recommended church. When you’re done, don’t forget to make a stop at the interesting Siena Cathedral. Round off your day at Piazza Del Duomo, another gem in Florence with inviting features to discover.

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 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.

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

Unwind after your meal by stepping into Gosh*. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Quelo Bar, another top-rated bar in the area.

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
  • Rome
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Drive 279 km, 4 hours 5 min

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

Dive into day 5 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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Colosseum. This culturally significant archeological site is sure to ignite your curiosity. Next, dive into the historic features of Roman Forum, a must-visit archeological site 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 Trevi Fountain, a timeless monument. For a change of scene, check out Piazza Navona, known for its enchanting features.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and spend some time relaxing before you head out to tour the city.

As you 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.

Enjoy a delicious meal at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 6

Day 6

  • Rome
  • More

Drive 11 km, 44 min

  • St Peter's Basilica
  • Piazza di Spagna
  • Trastevere
  • Monti
  • Via del Corso
  • More

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

Trastevere is a neighborhood that stands out as one of the must-see places in Vatican City. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Rome is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at St. Peter's Basilica, a wondrous major basilica that is worthwhile a visit in the city. Nearby, you’ll find Piazza Di Spagna, enchanting visitors with its awe-inspiring 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.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 7

Day 7

  • Rome
  • Naples
  • More

Drive 283 km, 3 hours 58 min

  • Castel Nuovo
  • piazza del Plebiscito
  • Ovo Castle
  • Archaeological Park of Pompeii
  • More

On day 7 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 Naples and Pompei. In the evening, you’ll end up in Naples, where you will stay for 1 night.

Start by visiting Castel Nuovo, a prime spot to begin your journey. This breathtaking castle is sure to impress. Next on your list is Piazza Del Plebiscito, another must-visit landmark and famous public square renowned for its romantic 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 Ovo Castle. This history-steeped castle is a remarkable attraction that offers a unique experience. Archaeological Park Of Pompeii also adds charm to your journey.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Naples. 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 L'Oca Nera Irish Pub, a popular restaurant in Naples. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Naples at Mimì alla Ferrovia, 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 Spuzzulè Winebar. It’s yet another ideal choice to enhance your time in Naples tonight.

After your meal, keep the night alive at a bar like Happening Cocktail Bar, known for its lively atmosphere. Shanti Art Musik Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Gran Caffè Gambrinus offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 8

Day 8

  • Naples
  • Ancona
  • More

Drive 534 km, 7 hours 19 min

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Ravello and Amalfi. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Ancona. You will spend 1 night here for some well-deserved relaxation.

Naples is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Villa Rufolo, a captivating historical landmark that is worthwhile a visit in the village. Continue your exploration at Saint Andrew's Fountain Amalfi. This monument is one of the village’s most locally appreciated spots.

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

Indulge in a memorable dining experience at one of Ancona's most popular restaurants, and connect with friendly locals for an authentic adventure.

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

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

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

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Day 9

Day 9

  • Ancona - Departure day
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  • Parco Della Cittadella di Ancona
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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 popular place to see in the city.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Ancona's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

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

If you're eager to try something different, consider Donegal Irish Pub, another top spot with a tantalizing 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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