4-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence
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Explore the best of Italy on a 4-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Florence, Siena, and San Gimignano. 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 and 1 night in Florence. 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. Ponte Vecchio and Piazzale Michelangelo are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Cathedral Of Santa Maria Del Fiore, learn more about the unique Piazza Della Signoria, and immerse yourself in the vibrant atmosphere of Piazza Del Campo.
As you hit the open road and drive through Ancona, Florence, Siena, and San Gimignano, 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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- 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.
As afternoon approaches, head to your chosen hotel in Ancona. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.
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.
If you’re not ready to end the night just yet, Posa Bar offers a perfect venue to relax and savor a drink. Similarly, Bar Four Roses is well-suited for those looking to unwind in a social setting. Amarillo Beer Bar Ancona is another excellent spot to enjoy a nightcap after a delightful meal.
Raise a toast to the start of your 4-day road trip in Italy!
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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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 1 night.
Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazzale Michelangelo. This spectacular observation deck is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Uffizi Gallery, one of the city’s best highlights.
Next, check out Ponte Vecchio, one of the most world-famous places to see in Ancona. This historical landmark is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Cathedral Of Santa Maria Del Fiore. Wander around and soak in the majestic atmosphere this church offers. Then, head to Piazza Della Signoria, a top-rated public square that adds another dimension to your day.
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 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 and reflect on the day's adventures.
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.
Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 3
- Florence
- Ancona
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Drive 392 km, 5 hours 33 min
- Siena Cathedral
- Battistero di San Giovanni Battista
- piazza del Campo
- Tower of Mangia
- Porta San Giovanni
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Dive into day 3 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, 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.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most notable attractions included on the itinerary is Siena Cathedral. This history-steeped church will help you start your sightseeing on top. Then, take a leisurely stroll to Battistero Di San Giovanni Battista and learn what makes this culturally significant church unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the widely recognized Piazza Del Campo. After exploring the public square, head to Tower Of Mangia. This underrated monument is a highlight in Florence. As your day continues, stop by Porta San Giovanni, known for its culturally significant features.
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.
After a day of adventure, treat yourself to an exquisite dinner at one of Ancona's best restaurants.
Treat yourself to a wonderful meal at Amarcord, a top-rated dining spot in Ancona. If you're in the mood for something new, try Bontà delle Marche, another premier location with a delectable menu. You might also want to book a table at Ristorante Pizzeria Da Romano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.
Continue the enjoyment post-dinner at Alla Tazza D'oro, a cherished local gathering spot renowned for its welcoming atmosphere.
Raise your glass to another unforgettable day in Italy!
Day 4
- Ancona - Departure day
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- Cattedrale di San Ciriaco
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Day 4 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 Cathedral Basilica Of St. Cyriacus, a monumental church before you head out.
Maximize your last day in Italy and go on a shopping spree in Ancona’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Ancona.
Treat yourself to a delightful dinner at Pizzeria Pulcinella, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Donegal Irish Pub? It's another excellent option with a diverse 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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