9-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to 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, Florence, Pisa, Castellina in Chianti, Greve in Chianti, Rome, Tivoli, and Santa Maria degli Angeli. 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, 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. 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, Castellina in Chianti, Greve in Chianti, Rome, Tivoli, and Santa Maria degli Angeli, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

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

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

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

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Lazzaretto of Ancona
piazzale MichelangeloUffizi GalleryPonte VecchioCathedral of Santa Maria del Fiorepiazza della Signoria
“Tuttomondo” (Keith Haring)Santa Maria del Carmine, PisaKnights' SquareLeaning Tower of PisaPisa CathedralPiazza del Duomo, Pisa
Parco Sculture del ChiantiRocca di Castellina in ChiantiCastle of VerrazzanoIl Molino di Grace
ColosseumRoman ForumTrevi FountainPantheonPiazza Navona
Vatican MuseumsSistine ChapelSt Peter's BasilicaAltare della PatriaPiazza di SpagnaTrastevere

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Day 1

Day 1

  • Ancona - Arrival day
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  • Lazzaretto of Ancona
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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 Lazzaretto Of Ancona, 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.

Enjoy a lovely dining experience at Playa Solero, a popular restaurant in Ancona. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Ancona at Zucchero a Velò, 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 Ristorante Il Giardino. It’s yet another ideal choice to enhance your time in Ancona tonight.

After your meal, keep the night alive at a bar like Posa Bar, known for its lively atmosphere. Bar Four Roses is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Amarillo Beer Bar Ancona offers an excellent atmosphere for those looking to amp up the evening.

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
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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.

Bring your curiosity for today’s adventure around Ancona. Some of the city’s most loved attractions await! Piazzale Michelangelo is the perfect place to start. This observation deck is one of the most spectacular places to visit in Ancona. Next, head to Uffizi Gallery, an extraordinary art gallery, known for its historic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Ponte Vecchio. This visually striking historical landmark is a highly recommended experience. Nearby, you'll also find Cathedral Of Santa Maria Del Fiore and Piazza Della Signoria. Visit these for an interesting touch to your journey.

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 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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 3

Day 3

  • Florence
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Drive 197 km, 3 hours 10 min

  • “Tuttomondo” (Keith Haring)
  • Santa Maria del Carmine, Pisa
  • Knights' Square
  • Leaning Tower of Pisa
  • Pisa Cathedral
  • Piazza del Duomo, Pisa
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Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 2 nights in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at “tuttomondo” (keith Haring). This photogenic art installation is a highlight of any visit in the city. Then, enjoy Santa Maria Del Carmine, Pisa, another culturally significant attraction that never fails to captivate visitors. Next, head over to Knights' Square, one of the city’s most intriguing attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Leaning Tower Of Pisa. This detailed monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Pisa Cathedral, a worthwhile church, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Duomo, Pisa before you head back to your hotel.

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

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 meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 4

Day 4

  • Florence
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Drive 186 km, 3 hours 53 min

  • Parco Sculture del Chianti
  • Rocca di Castellina in Chianti
  • Castle of Verrazzano
  • Il Molino di Grace
  • More

Wake up to day 4 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Bring your curiosity for today’s adventure around Florence. Some of the hamlet’s most loved attractions await! Parco Sculture Del Chianti is the perfect place to start. This sculpture garden is one of the most up-and-coming places to visit in Florence. Next, head to Rocca Di Castellina In Chianti, an up-and-coming castle, known for its history-steeped features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Castle Of Verrazzano. This romantic castle is a highly recommended experience. Nearby, you'll also find Il Molino Di Grace. Visit these for an interesting touch to your journey.

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

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.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 5

Day 5

  • Florence
  • Rome
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Drive 279 km, 4 hours 3 min

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

On day 5 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 Rome. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Discover a day packed with fun adventures, scenic views, and photo-friendly spots in Florence. Begin your sightseeing with Colosseum. This globally renowned archeological site is one of the top attractions in the city. Proceed to Roman Forum, another must-visit attraction.

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 Trevi Fountain. This iconic monument is a traveler-favorite. Not far away, you’ll find Pantheon, another key site on your sightseeing itinerary. Piazza Navona is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

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Day 6

Day 6

  • Rome
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Drive 13 km, 1 hour 21 min

  • Vatican Museums
  • Sistine Chapel
  • St Peter's Basilica
  • Altare della Patria
  • Piazza di Spagna
  • Trastevere
  • More

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

One of the most iconic places you can visit today in Vatican City is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Start your adventure at Vatican Museums. This iconic art museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Sistine Chapel located in Rome for another exciting encounter.

Next, immerse yourself in the setting of St. Peter's Basilica. After the major basilica, continue your tour of the city with a visit to Altare Della Patria. Visitors usually appreciate the culturally significant features of this monument. Next up is Piazza Di Spagna, a highly recommended public square.

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

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

Enjoy a delicious meal 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.

Round off your dining experience by visiting Sant' Eustachio Caffè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yellowsquare Rome, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 7

Day 7

  • Rome
  • More

Drive 74 km, 2 hours 4 min

  • Hadrian's Villa
  • Villa d'Este
  • Fontana dell'Organo
  • Fontana dell'Ovato (o di Tivoli)
  • Villa Gregoriana
  • Grande Cascata di Tivoli
  • More

On day 7 of your road trip, you’ll start and end your day in Rome, where you'll stay for 1 night more.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Hadrian's Villa. This culturally significant archeological site is sure to ignite your curiosity. Next, dive into the romantic features of Villa D'este, a must-visit palace in the town.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Fontana Dell'organo, a locally appreciated monument. For a change of scene, check out Fontana Dell'ovato (o Di Tivoli), known for its enchanting features. We also recommend visiting Villa Gregoriana. This park is a must for anyone looking to experience the town to the fullest. Lastly, end your day with a visit to Grande Cascata Di Tivoli, yet another beloved attraction in Rome.

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 Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar. It’s yet another ideal choice to enhance your time in Rome tonight.

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

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

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Day 8

Day 8

  • Rome
  • Ancona
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Drive 324 km, 4 hours 55 min

  • Basilica of San Francesco d'Assisi
  • Piazza del Comune
  • Basilica di Santa Chiara
  • Eremo delle Carceri
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Dive into day 8 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Ancona. You’ll stay here for 1 night.

Start by visiting Basilica Of San Francesco D'assisi, a prime spot to begin your journey. This breathtaking church is sure to impress. Next on your list is Piazza Del Comune, another must-visit landmark and frequently visited public square renowned for its enchanting features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Basilica Di Santa Chiara. This majestic church is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Eremo Delle Carceri, a worthwhile monastery.

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.

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

Savor the flavors at Amarcord, a top pick for dinner tonight. Alternatively, Bontà delle Marche beckons with its unique menu offerings. Also, consider Ristorante Pizzeria Da Romano. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.

After savoring a delicious meal, step into the vibrant nightlife at Alla Tazza D'oro, where the evening is just getting started.

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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  • Piazza del Plebiscito
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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, we recommend visiting Piazza Del Plebiscito, a visually striking public square before you head out.

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

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

Savor the flavors at Pizzeria Pulcinella, a top pick for dinner tonight. Alternatively, Donegal Irish Pub beckons with its unique menu offerings.

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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