4-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena
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Experience the freedom of the open road in Italy as you embark on an unforgettable 4-day road trip! This experience caters to every traveler, featuring destinations like Florence, Siena, San Gimignano, and Pisa.
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 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 got you covered.
Upon arriving in Florence, 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 Leaning Tower Of Pisa are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Del Duomo, Pisa, learn more about the unique Piazzale Michelangelo, and immerse yourself in the vibrant atmosphere of Cathedral Of Santa Maria Del Fiore.
As you hit the open road and drive through Florence, Siena, San Gimignano, and Pisa, 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
- Florence - Arrival day
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- piazzale Michelangelo
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Say hello to Florence! 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 Florence for 1 night before you continue your adventure!
Florence 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 Piazzale Michelangelo, 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.
Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.
After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.
Raise a toast to the start of your 4-day road trip in Italy!
Day 2
- Florence
- Siena
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Drive 80 km, 1 hour 34 min
- piazza della Signoria
- Ponte Vecchio
- Uffizi Gallery
- Basilica of Santa Croce in Florence
- Siena Cathedral
- piazza del Campo
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Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Florence and Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.
Today, you'll explore some of the most beautiful places in Florence, including a public square, a historical landmark, an art gallery, a church and much more! Start your day with a visit to Piazza Della Signoria. This top-rated public square is a must-visit in the city. When you’re ready for your next discovery, continue to Ponte Vecchio, which may be one of the most grand places you will experience today.
One of the best things about exploring Florence 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 Uffizi Gallery, an astonishing art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of Santa Croce In Florence and Siena Cathedral. End your day with a visit to Piazza Del Campo, a top-rated public square that’s sure to leave a lasting impression.
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.
As you explore more of Siena, 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.
Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.
After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.
Raise your glass to another unforgettable day in Italy!
Day 3
- Siena
- Florence
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Drive 213 km, 3 hours 54 min
- Porta San Giovanni
- Santa Maria della Spina
- Knights' Square
- Leaning Tower of Pisa
- Piazza del Duomo, Pisa
- Pisa Cathedral
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On day 3 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 San Gimignano and Pisa. In the evening, you’ll end up in Florence, where you will stay for 1 night.
Today’s agenda in Siena includes a monument, a church, and a public square. Porta San Giovanni is must-visit monument and a great starting point for the day. Next, continue your journey to Santa Maria Della Spina, a locally appreciated church, located just a leisurely stroll away. Next, head to Knights' Square, an instagrammable public square, also available for your discovery today.
Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the world-famous Leaning Tower Of Pisa. If you’re looking for more, Piazza Del Duomo, Pisa is also an iconic attraction that is worthwhile a visit. Lastly, don’t miss Pisa Cathedral, a place of UNESCO world heritage-listed interest in the village.
When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.
Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.
Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.
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.
Celebrate another amazing day of your road trip adventure in Italy!
Day 4
- Florence - Departure day
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- Cathedral of Santa Maria del Fiore
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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 Florence 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 Of Santa Maria Del Fiore. This famous church is a popular place to see in the city.
Maximize your last day in Italy and go on a shopping spree in Florence’s shopping center, the lively San Lorenzo Market. 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 Florence.
If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu.
You’ll then say farewell to Florence. 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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