One-Week 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 8-day road trip! This experience caters to every traveler, featuring destinations like Ancona, Florence, Pisa, Siena, San Gimignano, and Rome.
This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Ancona, 2 nights in Florence, 1 night in Siena, and 1 night 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, Siena, San Gimignano, and Rome, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.
Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.
This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.
The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!
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Day 1
- Ancona - Arrival day
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- Parco Della Cittadella di 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 2 nights 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 Parco Della Cittadella Di 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.
Treat yourself to a delicious dinner at Playa Solero, an excellent option for tonight's dining. Looking for something different? Zucchero a Velò offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Il Giardino. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Ancona.
After savoring a delicious meal, step into the vibrant nightlife at Posa Bar, where the evening is just getting started. In the same way, Bar Four Roses offers a unique charm perfect for experiencing the local bar scene in Ancona. Amarillo Beer Bar Ancona is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Raise a toast to the start of your 8-day road trip in Italy!
Day 2
- Ancona
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Drive 17 km, 1 hour 18 min
- Parco Belvedere Posatora
- Lazzaretto of Ancona
- Piazza del Plebiscito
- Arch of Trajan
- Grotta Azzurra Pathway
- Passetto
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Day 2 of your road trip across Italy promises a magnificent time exploring Ancona. You have 1 night left in Ancona. Take the opportunity to experience more of the best attractions and activities in the city.
Today’s itinerary in Ancona covers several incredible sights, including a park, a museum, a public square, a monument, a cave and much more! Start your adventure at Parco Belvedere Posatora. This beloved park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Lazzaretto Of Ancona, a must-see museum 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 Plebiscito. This worthwhile public square offers an enriching experience. For a change of pace, head to Arch Of Trajan, where you can take in picture-perfect features. Conclude your self-guided sightseeing tour with a visit to Grotta Azzurra Pathway and Passetto. These sights offer a fulfilling end to a perfect day.
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 Ancona. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
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.
Continue your evening by exploring the vibrant nightlife scene at Alla Tazza D'oro, a prime destination for a thrilling night out.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 3
- Ancona
- Florence
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Drive 277 km, 3 hours 40 min
- Basilica of Santa Croce in Florence
- Uffizi Gallery
- Ponte Vecchio
- Palazzo Vecchio
- piazza della Signoria
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.
Today’s well-planned self-sightseeing route offers several fun adventures, photo-friendly spots, and history-rich sites. Whether you decide to explore Ancona on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Basilica Of Santa Croce In Florence is the first of them. Spend some time admiring this heritage-rich church before continuing your journey. Uffizi Gallery is your next stop. This astonishing art gallery is one of the best-rated sights in Ancona.
Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Ponte Vecchio. This history-steeped historical landmark is a sight to behold. To round off your sightseeing experience, visit Palazzo Vecchio and Piazza Della Signoria.
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.
Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.
Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.
Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.
Get a good night's sleep and look forward to another great day on the road in Italy!
Day 4
- Florence
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Drive 196 km, 3 hours 7 min
- Santa Maria della Spina
- Palazzo Blu
- Knights' Square
- Leaning Tower of Pisa
- Pisa Cathedral
- Piazza del Duomo, Pisa
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On day 4 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Santa Maria Della Spina is the first of them. Spend some time admiring this romantic church before continuing your journey. Palazzo Blu is your next stop. This locally appreciated art gallery is one of the best-rated sights in Florence.
Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Knights' Square. This stunning public square is a sight to behold. To round off your sightseeing experience, visit Leaning Tower Of Pisa and Pisa Cathedral. If time allows, end your day with Piazza Del Duomo, Pisa, a historic public square that offers a memorable conclusion to your exploration.
When you’re done exploring for the day, you’ll return to Florence and your accommodation.
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.
Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 5
- Florence
- Siena
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Drive 158 km, 2 hours 58 min
- Siena Cathedral
- piazza del Campo
- Tower of Mangia
- Porta San Giovanni
- SanGimignano1300
- Piazza del Duomo, San Gimignano
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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 Siena and San Gimignano. In the evening, you’ll end up in Siena, where you will stay for 1 night.
Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Siena Cathedral. This interesting church is one of the top attractions in the city. Proceed to Piazza Del Campo, 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 Tower Of Mangia. This often recommended monument is a traveler-favorite. Not far away, you’ll find Porta San Giovanni, another key site on your sightseeing itinerary. Sangimignano1300 is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Duomo and uncover why it's recognized as one of the city's most locally appreciated attractions.
At the end of the day, you will drive to Siena, 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 Siena's best restaurants.
Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.
Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 6
- Siena
- Rome
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Drive 242 km, 3 hours 37 min
- Colosseum
- Roman Forum
- Trevi Fountain
- Pantheon
- Piazza Navona
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Embark on another extraordinary experience on day 6 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 1 night.
Start by visiting Colosseum, a prime spot to begin your journey. This UNESCO world heritage-designated archeological site is sure to impress. Next on your list is Roman Forum, another must-visit landmark and iconic archeological site renowned for its UNESCO world heritage-listed features.
While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Trevi Fountain. This history-steeped monument is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Pantheon, a globally renowned monument. Nearby, you'll also find Piazza Navona, ready to add charm to your journey.
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 lovely meal at La Bottega Roma, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Pasta In Corso is another top choice with a popular menu. You could also check for a table at Trattoria Vecchia Roma. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.
After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Celebrate another amazing day of your road trip adventure in Italy!
Day 7
- Rome
- Ancona
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Drive 313 km, 4 hours 17 min
- St Peter's Basilica
- Sistine Chapel
- Obelisk of St Peter's Square
- Vatican Museums
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Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Vatican City. 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.
Start your day with a visit to St. Peter's Basilica. This wondrous major basilica is a must-visit in the city.
One of the best things about exploring Rome 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 Obelisk Of St Peter's Square, an increasingly popular point of interest in the city. If you’re up for more discoveries, don’t forget to reserve some time for Vatican Museums.
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.
As dinnertime approaches, it's time to head out for a bite to eat in Ancona. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
Have a fantastic dining experience at Pizzeria Pulcinella, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Donegal Irish Pub offers an enticing alternative with its varied menu. Additionally, Vino E Cucina Miscia is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Ancona.
Savor another day of unforgettable experiences in Italy!
Day 8
- Ancona - Departure day
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- Cattedrale di San Ciriaco
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Day 8 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 Cathedral Basilica Of St. Cyriacus. This beloved church is a popular place to see in the city.
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.
Have a fantastic dining experience at Mixer Bar, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria La Bottega Di Pinocchio offers an enticing alternative with its varied 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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