10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Pescara, Rome, Florence, and Siena

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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.
10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Pescara, Rome, Florence, and Siena
10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Pescara, Rome, Florence, and Siena
10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Pescara, Rome, Florence, and Siena
10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Pescara, Rome, Florence, and Siena
10-Day Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Pescara, Rome, Florence, and Siena
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Escape the ordinary with this exciting 10-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, 1 night in Pescara, 3 nights in Rome, 2 nights in Florence, and 1 night in Siena. 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, Loreto, Pescara, Rome, Florence, Pisa, Siena, 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, 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
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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 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.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Ancona. Make yourself at home and unwind 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.

Continue your lively evening at Posa Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Four Roses is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Amarillo Beer Bar Ancona ensures a night out tailored to your taste.

Raise a toast to the start of your 10-day road trip in Italy!

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Day2

Day 2

  • Ancona
  • Loreto
  • Pescara
  • More

Drive 275 km, 3 hours 42 min

  • Frasassi Caves
  • San Vittore alle Chiuse
  • Sanctuary of the Holy House of Loreto
  • More

On day 2 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. San Vittore and Loreto are on today's agenda. In the evening, you’ll end up in Pescara, where you will stay for 1 night.

When you’ve had your share of Ancona, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of San Vittore. Your travel time is around 52 min.

Our first attraction recommendation in San Vittore is Frasassi Caves, a popular cave system that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to San Vittore Alle Chiuse, a historic church that stands out in the hamlet.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Loreto may take around 59 min. Upon your arrival in Loreto, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Sanctuary Of The Holy House Of Loreto, a notable church known for its stunning features.

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

Pescara 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 Pescara.

Enjoy an outstanding dining experience at Nole, a Bib Gourmand restaurant offering an exceptional italian contemporary and italian menu. Alternatively, if you're in the mood for something different, consider the nearby Bib Gourmand-awardee, Estrò, known for its delicious contemporary and country cooking cuisine. Another highly-recommended place to eat in Pescara is Taverna 58, a renowned Bib Gourmand restaurant and a delicious from abruzzo and traditional menu.

Explore the vibrant nightlife at Posa Caffè Pescara after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Mixer for a great selection of flavorful drinks and a charming setting. Furthermore, Temple Bar Irish Pub is perfect for those looking to extend their night with a touch of local flavor.

Relax and look forward to more memorable moments to come!

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Day3

Day 3

  • Pescara
  • Vatican City
  • Rome
  • More

Drive 226 km, 3 hours 7 min

  • Vatican Museums
  • Saint Peter's Square
  • Sistine Chapel
  • St Peter's Basilica
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

Continue your road trip and head to your next destination, Vatican City, Vatican City. This car ride takes around 2 hours 23 min.

Savor the day by heading to Vatican Museums, a world-famous art museum that draws visitors from near and far.

Next, explore Sistine Chapel, yet another spectacular place to see in the area. After the chapel, make time to go to St. Peter's Basilica.

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.

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

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

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

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Day4

Day 4

  • Rome
  • More

Drive 11 km, 1 hour 19 min

  • Castel Sant'Angelo
  • Piazza Navona
  • Pantheon
  • Trevi Fountain
  • Villa Borghese
  • More

On day 4 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 2 nights.

No visit to Rome is complete without Castel Sant'angelo. This top-rated castle is one of the top attractions in the city. Proceed to Piazza Navona, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Pantheon. This timeless monument is a traveler-favorite. Not far away, you’ll find Trevi Fountain, another key site on your sightseeing itinerary. Villa Borghese is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Rome 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 Rome.

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. Known for great service, it’s a fantastic choice for tonight in Rome.

After savoring a delicious meal, step into the vibrant nightlife at Sant' Eustachio Caffè, where the evening is just getting started. In the same way, Yellowsquare Rome offers a unique charm perfect for experiencing the local bar scene in Rome. Caffè Portofino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Relax and look forward to more memorable moments to come!

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Day5

Day 5

  • Rome
  • More

Drive 3 km, 41 min

  • Altare della Patria
  • Roman Forum
  • Colosseum
  • Trastevere
  • Monti
  • More

Day 5 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Rome.

A visit to Trastevere is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights. Don’t forget to check out Monti as well, a neighborhood that adds another layer to your exploration.

Whatever your travel style is, Altare Della Patria is an essential stop in Rome. This notable monument provides an insightful glimpse into the city's identity. Next, discover Roman Forum, a culturally significant archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Colosseum, a wondrous archeological site.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Rome tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

Raise your glass to another unforgettable day in Italy!

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Day6

Day 6

  • Rome
  • Florence
  • More

Drive 278 km, 3 hours 35 min

  • Piazza di Spagna
  • Spanish Steps
  • piazza del Popolo
  • More

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 2 nights.

Catch Piazza Di Spagna before the crowds roll in. This enchanting public square is sure to ignite your curiosity. Next, dive into the history-steeped features of Spanish Steps, a must-visit public square 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 Piazza Del Popolo, a famous public square.

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.

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.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day7

Day 7

  • Florence
  • More

Drive 4 km, 59 min

  • piazzale Michelangelo
  • Uffizi Gallery
  • piazza della Signoria
  • Ponte Vecchio
  • Oltrarno
  • More

Day 7 offers an itinerary packed with the best things to see in Ancona. You’ll stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

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

Make time for Piazzale Michelangelo, a famous observation deck that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its respected appeal. Continue your exploration at Piazza Della Signoria. This public square is one of the city’s most famous spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Ponte Vecchio.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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 Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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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Day8

Day 8

  • Florence
  • Pisa
  • Siena
  • More

Drive 210 km, 3 hours 24 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • 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 places, which are Florence and Pisa. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

No visit to Florence is complete without Cathedral Of Santa Maria Del Fiore. This widely recognized church is one of the top attractions in the city. Proceed to Central Market, another must-visit attraction.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 1 hour 18 min. When you arrive in Pisa, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Leaning Tower Of Pisa and explore the breathtaking features. Next, make your way to Piazza Del Duomo, Pisa, another highlight in Pisa.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Siena. Siena 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day9

Day 9

  • Siena
  • Assisi
  • Ancona
  • More

Drive 257 km, 4 hours

  • piazza del Campo
  • Siena Cathedral
  • Fortezza Medicea
  • Basilica of San Francesco d'Assisi
  • More

Your itinerary for day 9 of your road trip in Italy includes 2 stops and features some of the highlights of Siena and Santa Maria degli Angeli. At the end of the day, enjoy the comforts of a top-rated hotel in Ancona, where you'll spend 1 night.

Look forward to a unique sightseeing adventure at the top-rated Piazza Del Campo and allow yourself time to explore. Just a short distance away you'll find your next stop, Siena Cathedral, an inviting church that draws visitors from far and near.

Continue your journey to Fortezza Medicea (siena), one of the city’s most worthwhile spots that you shouldn’t miss.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Santa Maria degli Angeli. 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 41 min. Upon reaching Santa Maria degli Angeli, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Basilica Of San Francesco D'assisi is a well-known church we recommend visiting today. Discover its breathtaking features before continuing your self-guided tour.

At the end of the day, you will drive to Ancona, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

Treat yourself to an extraordinary dining experience at Sot'Ajarchi, a Bib Gourmand restaurant offering an incredible seafood and from the marches menu. Alternatively, if your taste buds call for something different, Bontà delle Marche is another top choice with a popular menu.

Continue the enjoyment post-dinner at Alla Tazza D'oro, a cherished local gathering spot renowned for its welcoming atmosphere.

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

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Day10

Day 10

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

Day 10 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Ancona before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, we recommend visiting Parco Della Cittadella Di Ancona, a romantic park before you head out.

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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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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