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

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Experience the freedom of the open road in Italy as you embark on an unforgettable 11-day road trip! This experience caters to every traveler, featuring destinations like Ancona, Florence, Pisa, Lucca, Siena, San Gimignano, Volterra, Rome, Santa Maria degli Angeli, and Perugia.

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 Siena, 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, Lucca, Siena, San Gimignano, Volterra, Rome, Santa Maria degli Angeli, and Perugia, 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
Palazzo PittiPonte VecchioUffizi Gallerypiazza della Signoria
DavidGalleria dell'AccademiaCentral MarketCathedral of Santa Maria del FioreBasilica of Santa Croce in Florencepiazzale Michelangelo
“Tuttomondo” (Keith Haring)Leaning Tower of PisaPiazza del Duomo, PisaPisa CathedralWalls of Lucca
Fortezza MediceaVista Panoramica de SienaSiena Cathedralpiazza del CampoPubblico PalacePorta Pispini
Piazza del Duomo, San GimignanoChiesa di Sant'AgostinoCathedral of Santa Maria AssuntaParco Archeologico "Enrico Fiumi"Etruscan Museum "Mario Guarnacci"

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Day 1

Day 1

  • Ancona - Arrival day
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  • Piazza del Plebiscito
  • More

Say hello to Ancona! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Ancona for 1 night before you continue your adventure!

Ancona is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Piazza Del Plebiscito, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Ancona. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Ancona, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Playa Solero, a top-rated dining spot in Ancona. If you're in the mood for something new, try Zucchero a Velò, another premier location with a delectable menu. You might also want to book a table at Ristorante Il Giardino. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Posa Bar, known for its inviting atmosphere. Bar Four Roses is another great option if you’re looking for a place to get the night started. Similarly, Amarillo Beer Bar Ancona provides a great setting to enjoy the night away.

Raise a toast to the start of your 11-day road trip in Italy!

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Day 2

Day 2

  • Ancona
  • Florence
  • More

Drive 285 km, 3 hours 37 min

  • Palazzo Pitti
  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • More

On day 2 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Today’s itinerary in Ancona covers several incredible sights, including a palace, a historical landmark, an art gallery, a public square and much more! Start your adventure at Pitti Palace. This well-known palace is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the awe-inspiring wonders of Ponte Vecchio, a must-see historical landmark in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Uffizi Gallery. This famous art gallery offers an enriching experience. For a change of pace, head to Piazza Della Signoria, where you can take in noteworthy features.

At the end of the day, you will drive to Florence, 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 Florence, 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.

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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

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Day 3

Day 3

  • Florence
  • More

Drive 9 km, 1 hour 19 min

  • David
  • Galleria dell'Accademia
  • Central Market
  • Cathedral of Santa Maria del Fiore
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Get ready for a day filled with family-friendly attractions, picturesque spots, and history-rich sites in the charming city of Florence. Your adventure starts at David, an interesting local hot spot. Another notable attraction to explore is Galleria Dell'accademia.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Central Market. This instagrammable food market offers a fascinating experience that many visitors find memorable. Cathedral Of Santa Maria Del Fiore is also worth visiting, along with Basilica Of Santa Croce In Florence. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazzale Michelangelo. This impressive observation deck provides a fitting finale to your sightseeing.

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 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 Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for 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 4

Day 4

  • Florence
  • More

Drive 195 km, 3 hours 18 min

  • “Tuttomondo” (Keith Haring)
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Walls of Lucca
  • More

On day 4 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 1 night more, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary!

Today’s itinerary in Florence covers several incredible sights, including an art installation, a monument, a public square, a church, a historical landmark and much more! Start your adventure at “tuttomondo” (keith Haring). This locally appreciated art installation is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Leaning Tower Of Pisa, a must-see monument in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Piazza Del Duomo, Pisa. This timeless public square offers an enriching experience. For a change of pace, head to Pisa Cathedral, where you can take in symbolic features. Conclude your self-guided sightseeing tour with a visit to Mura Di Lucca and Mura Di Lucca. These sights offer a fulfilling end to a perfect day.

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

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.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Following your dinner, dive into the local bar culture at Gosh*. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Antico Caffè Del Moro - Art Bar Firenze, the perfect place for those looking to experience the best of the nightlife. Similarly, Quelo Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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
  • Siena
  • More

Drive 79 km, 2 hours 6 min

  • Fortezza Medicea
  • Vista Panoramica de Siena
  • Siena Cathedral
  • piazza del Campo
  • Pubblico Palace
  • Porta Pispini
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Florence is brimming with adventures. Today’s wonderful stops include a monument, an observation deck, a church, a public square, a palace, a historical landmark and much more! Begin your sightseeing adventure at the underrated Fortezza Medicea (siena). Just a short distance away is Vista Panoramica De Siena, a visually striking observation deck that draws visitors from far and near.

Continue your journey to Siena Cathedral, one of the city’s most notable spots that you shouldn’t miss. Another great site to visit is the extraordinary Piazza Del Campo. Last up on today’s itinerary is a palace. Make your way to Pubblico Palace for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Florence.

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!

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Day 6

Day 6

  • Siena
  • More

Drive 132 km, 2 hours 55 min

  • Piazza del Duomo, San Gimignano
  • Chiesa di Sant'Agostino
  • Cathedral of Santa Maria Assunta
  • Parco Archeologico "Enrico Fiumi"
  • Etruscan Museum "Mario Guarnacci"
  • More

On day 6 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Bring your curiosity for today’s adventure around Siena. Some of the village’s most loved attractions await. Piazza Del Duomo is the perfect place to start. This public square is one of the most intriguing places to visit in Siena. Next, head to Chiesa Di Sant'agostino, a locally appreciated church, known for its photogenic 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 Cathedral Of Santa Maria Assunta. This breathtaking church offers a unique experience that is highly recommended. Meanwhile, Parco Archeologico "enrico Fiumi" adds its own distinct charm to your journey. Finish your day with a visit to Etruscan Museum "mario Guarnacci", a respected museum in Siena.

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

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.

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Pinacoteca, a bar that offers unique local touches. Likewise, San Paolo Pub provides an excellent alternative for a fun evening.

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 7

Day 7

  • Siena
  • Rome
  • More

Drive 237 km, 3 hours 39 min

  • Castel Sant'Angelo
  • Campo de' Fiori
  • Piazza Navona
  • Pantheon
  • Altare della Patria
  • Circus Maximus
  • More

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Castel Sant'angelo. This history-steeped castle is a highlight of any visit in the city. Then, enjoy Campo De' Fiori, another respected attraction that never fails to captivate visitors. Next, head over to Piazza Navona, one of the city’s most timeless attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This instagrammable monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Altare Della Patria, a well-known monument, and take a stroll around the area.

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

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.

Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

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Day 8

Day 8

  • Rome
  • More

Drive 15 km, 58 min

  • Vatican Museums
  • Sistine Chapel
  • St Peter's Basilica
  • piazza del Popolo
  • Trastevere
  • Monti
  • More

On day 8 of your road trip, you will have an entire day to explore Vatican City. You’ll stay in Rome for 2 nights and discover all the best things to see and do in the area.

A top thing to do today is to explore Trastevere, a must-see neighborhood in Vatican City. It's the perfect starting point for touring the top attractions in the area. You can also visit Monti, an ideal neighborhood for continued sightseeing.

Rome is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Vatican Museums, a globally renowned art museum that is worthwhile a visit in the city. Continue your exploration at St. Peter's Basilica. This major basilica is one of the city’s most globally renowned spots.

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

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.

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino 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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Day 9

Day 9

  • Rome
  • More

Drive 10 km, 1 hour 21 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Piazza di Spagna
  • Spanish Steps
  • Villa Borghese
  • More

Day 9 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Colosseum. This world-famous archeological site provides an insightful glimpse into the city's identity. Next, discover Roman Forum, an UNESCO world heritage-listed archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Trevi Fountain, a wondrous monument. When you’re done, don’t forget to make a stop at the globally renowned Piazza Di Spagna. Round off your day at Spanish Steps, another gem in Rome with visually striking features to discover.

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.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

Savor another day of unforgettable experiences in Italy!

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Day 10

Day 10

  • Rome
  • Ancona
  • More

Drive 343 km, 5 hours 1 min

  • Church of Santa Maria sopra Minerva in Assisi
  • Basilica of San Francesco d'Assisi
  • National Gallery
  • Piazza IV Novembre
  • More

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Church Of Santa Maria Sopra Minerva In Assisi. This beloved church provides an insightful glimpse into the town's identity. Next, discover Basilica Of San Francesco D'assisi, a historic church, promising a delightful encounter.

Continue your sightseeing with a visit to National Gallery, a beloved art gallery. When you’re done, don’t forget to make a stop at the intriguing Piazza Iv Novembre.

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 long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Ancona. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely dining experience at Amarcord, 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 Bontà delle Marche, 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 Pizzeria Da Romano. It’s yet another ideal choice to enhance your time in Ancona tonight.

To truly maximize your evening out, consider visiting Alla Tazza D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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 11

Day 11

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

Day 11 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.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

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 for something new, try Donegal Irish Pub, another premier location with a delectable 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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