7-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena
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Escape the ordinary with this exciting 7-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!
This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 4 nights in Florence and 2 nights 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, Pisa, Lucca, Siena, San Gimignano, Castellina in Chianti, 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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Day 1
- Florence - Arrival day
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- Cathedral of Santa Maria del Fiore
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Welcome to Florence, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 3 nights immersing yourself in Florence's charm before embarking on the next leg of your journey.
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 Cathedral Of Santa Maria Del Fiore, 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.
Enjoy a lovely dining experience at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.
Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.
Raise a toast to the start of your 7-day road trip in Italy!
Day 2
- Florence
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Drive 9 km, 1 hour 16 min
- Galleria dell'Accademia
- piazza della Signoria
- Ponte Vecchio
- Uffizi Gallery
- Basilica of Santa Croce in Florence
- piazzale Michelangelo
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Day 2 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.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Galleria Dell'accademia. This interesting art gallery provides an insightful glimpse into the city's identity. Next, discover Piazza Della Signoria, a remarkable public square, promising a delightful encounter.
Continue your sightseeing with a visit to Ponte Vecchio, a globally renowned historical landmark. When you’re done, don’t forget to make a stop at the top-rated Uffizi Gallery. Not far away from the art gallery, you will find the romantic Piazzale Michelangelo, perfect for a quick visit. Round off your day at Basilica Of Santa Croce In Florence, another gem in Florence with culturally significant 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.
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.
Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.
Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.
Say good night to Florence and look forward to another great day of your road trip in Italy!
Day 3
- Florence
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Drive 196 km, 3 hours 14 min
- Piazza del Duomo, Pisa
- Leaning Tower of Pisa
- Guinigi Tower
- San Michele in Foro
- Walls of Lucca
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Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa and Lucca.
Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Del Duomo, Pisa. This historic public square is sure to ignite your curiosity. Next, dive into the picture-perfect features of Leaning Tower Of Pisa, a must-visit monument 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 Guinigi Tower, an intriguing monument. For a change of scene, check out San Michele In Foro, known for its stunning features. We also recommend visiting Mura Di Lucca. This historical landmark is a must for anyone looking to experience the city to the fullest.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.
Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. 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 4
- Florence
- Siena
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Drive 162 km, 2 hours 55 min
- Siena Cathedral
- piazza del Campo
- Pubblico Palace
- Parco della Rocca
- SanGimignano1300
- Piazza del Duomo, San Gimignano
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On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.
Discover a day packed with fun adventures, romantic experiences, and scenic views in Florence. Begin your sightseeing with Siena Cathedral. This well-known 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 Pubblico Palace. This worthwhile palace is a traveler-favorite. Not far away, you’ll find Parco Della Rocca, 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 often recommended 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.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time 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!
Day 5
- Siena
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Drive 73 km, 1 hour 58 min
- Castello di Brolio
- Tumulo di Montecalvario
- Rocca di Castellina in Chianti
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Wake up to day 5 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!
Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Castello Di Brolio. This beloved castle is a respected place to see in Siena. Continue your discovery at Tumulo Di Montecalvario, a photogenic archeological site with stories to tell.
As you stroll around Siena, take in the distinct atmosphere and learn what makes this hamlet so unique. Maximize your sightseeing with a visit to Rocca Di Castellina In Chianti. This often recommended castle offers a visually striking encounter with Siena. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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.
Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.
After your delicious meal, get a taste of the vibrant nightlife with a visit to Charlie Mixology Bar Di Aldinucci Riccardo, known for its inviting atmosphere. Bar Pinacoteca is another great option if you’re looking for a place to get the night started. Similarly, San Paolo Pub provides a great setting to enjoy the night away.
Relax and recharge in preparation for another adventurous day in Italy!
Day 6
- Siena
- Florence
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Drive 308 km, 4 hours 33 min
- Basilica of San Francesco d'Assisi
- Rocca Maggiore
- The Fontana Maggiore
- Piazza IV Novembre
- Perugia Cathedral
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On day 6 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 Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Florence, where you will stay for 1 night.
Get ready for a day filled with family-friendly attractions, breathtaking views, and photo-friendly spots in the charming town of Siena. Your adventure starts at Basilica Of San Francesco D'assisi, a captivating local hot spot. Another notable attraction to explore is Rocca Maggiore. This frequently visited castle is known for its grand appeal.
After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to The Fontana Maggiore. This detailed monument offers a fascinating experience that many visitors find memorable. Piazza Iv Novembre is also worth visiting, along with Perugia Cathedral. These standout landmarks offer unique experiences that add to the day’s enjoyment.
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.
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.
Treat yourself to a delightful dinner at Tijuana, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Djària - American Bar? It's another excellent option with a diverse menu. Consider reserving a table at The Florence Irish Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 7
- Florence - Departure day
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- Oltrarno
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Day 7 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.
At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.
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 Florence.
If you're in the mood to try something new, consider Essenziale, another top spot with a mouthwatering 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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