7-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Florence and San Gimignano
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Explore the best of Italy on a 7-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bologna, Florence, Siena, San Gimignano, Pisa, Lucca, Greve in Chianti, and Gaiole in Chianti. 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 3 nights in Bologna, 2 nights in Florence, and 1 night in San Gimignano. 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 Bologna, 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 Bologna, Florence, Siena, San Gimignano, Pisa, Lucca, Greve in Chianti, and Gaiole in Chianti, 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
- Bologna - Arrival day
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- arco del Meloncello
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Welcome to Bologna, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 2 nights immersing yourself in Bologna's charm before embarking on the next leg of your journey.
Bologna 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 Arco Del Meloncello, 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 Bologna. 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 Bologna, it's often a good idea to reserve a table in advance.
Enjoy a delicious meal at Ristorante Ciacco, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Ristorante Ballarini, another top spot with a mouthwatering menu. You might also want to secure a reservation at Sfoglia Rina. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.
Keep the evening going at Bar Al Bricco D'oro, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Freud E Squisito, which offers a similarly pleasant setting and great drinks. Another option is Osteria Del Sole, which provides an inviting environment for unwinding after a busy day out.
Raise a toast to the start of your 7-day road trip in Italy!
Day 2
- Bologna
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Drive 3 km, 42 min
- Pinacoteca Nazionale di Bologna
- Two Towers
- Piazza Santo Stefano
- Piazza Maggiore
- Bologna Cathedral
- Fountain of Neptune, Bologna
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On day 2 of your road trip, you will have an entire day to explore Bologna. You’ll stay in Bologna for 1 night and discover all the best things to see and do in the area.
Bologna is home to plenty of attractions that offer fun adventures, photo-friendly spots, and history-rich sites! Start at Pinacoteca Nazionale Di Bologna, a worthwhile art gallery that is worthwhile a visit in the city. Nearby, you’ll find Two Towers, enchanting visitors with its picture-perfect appeal. Continue your exploration at Piazza Santo Stefano. This public square is one of the city’s most underrated spots.
Enjoy the freedom of exploring Bologna 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 Maggiore. After exploring the public square, head to the up-and-coming Bologna Cathedral. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Fountain Of Neptune, Bologna, a place of photogenic interest in Bologna.
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 Bologna's most popular restaurants, and connect with friendly locals for an authentic adventure.
Dine in style at Bononia Cafè, a top recommendation for dinner tonight. Or, for a change of pace, Via Con Me boasts a menu that's sure to impress. Also, be sure to check out Trattoria Pizzeria La Mela. Known as a local hotspot, it’s a great choice for tonight in Bologna.
Continue your lively evening at Lime Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Macondo - Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Onda Marina By Night ensures a night out tailored to your taste.
Say good night to Bologna and look forward to another great day of your road trip in Italy!
Day 3
- Bologna
- Florence
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Drive 118 km, 2 hours 20 min
- piazzale Michelangelo
- Basilica of Santa Croce in Florence
- Uffizi Gallery
- Ponte Vecchio
- Palazzo Vecchio
- Cathedral of Santa Maria del Fiore
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Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazzale Michelangelo is the first of them. Spend some time admiring this culturally significant observation deck before continuing your journey. Basilica Of Santa Croce In Florence is your next stop. This captivating church is one of the best-rated sights in Bologna.
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 Uffizi Gallery. This instagrammable art gallery is a sight to behold. To round off your sightseeing experience, visit Ponte Vecchio and Palazzo Vecchio. If time allows, end your day with Cathedral Of Santa Maria Del Fiore, a symbolic church that offers a memorable conclusion to your exploration.
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.
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.
Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.
After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.
Celebrate another amazing day of your road trip adventure in Italy!
Day 4
- Florence
- San Gimignano
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Drive 121 km, 2 hours 28 min
- Fortezza Medicea
- Basilica of San Domenico
- Tower of Mangia
- piazza del Campo
- Siena Cathedral
- Piazza del Duomo, San Gimignano
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Dive into day 4 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 San Gimignano. You’ll stay here for 1 night.
Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Fortezza Medicea (siena). This increasingly popular monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of San Domenico, one of the city’s best highlights.
Next, check out Tower Of Mangia, one of the most frequently visited places to see in Florence. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Campo. Wander around and soak in the history-steeped atmosphere this public square offers. Then, head to Siena Cathedral, a top-rated church that adds another dimension to your day. Finally, visit the beloved Piazza Del Duomo, the last of our attraction recommendations for today.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in San Gimignano. San Gimignano 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 San Gimignano's best restaurants.
Savor another day of unforgettable experiences in Italy!
Day 5
- San Gimignano
- Florence
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Drive 193 km, 3 hours 25 min
- Pisa Cathedral
- Piazza del Duomo, Pisa
- Leaning Tower of Pisa
- Walls of Lucca
- Piazza dell'Anfiteatro
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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 Pisa and Lucca. In the evening, you’ll end up in Florence, where you will stay for 1 night.
A blend of family-friendly attractions, breathtaking views, and photo-friendly spots await you in San Gimignano on today’s itinerary. First up is the intriguing church, Pisa Cathedral. Afterward, continue to Piazza Del Duomo, Pisa, a public square every traveler should visit.
As you explore San Gimignano’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Leaning Tower Of Pisa. This globally renowned monument is an essential stop. Following that, head to Mura Di Lucca, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Dell'anfiteatro, an interesting public square in the city.
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.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.
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 evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.
Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!
Day 6
- Florence
- Bologna
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Drive 249 km, 4 hours 18 min
- Castle of Verrazzano
- Castello di Brolio
- Capannelle
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On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Greve in Chianti, San Regolo, and Gaiole in Chianti. When you’re not sightseeing, take time to relax at your selected hotel in Bologna, where you’ll be staying for 1 night.
Savor the day by visiting some of the best places to see in Florence, including a castle and a winery. Start your adventure at Castle Of Verrazzano. This beloved castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Castello Di Brolio located in Florence for another exciting encounter.
Next, immerse yourself in the setting of Capannelle. Its mesmerizing features will captivate you.
When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. 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 delicious dinner at Va Mo Là, an excellent option for tonight's dining. Looking for something different? Trattoria dal Biassanot offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Enoteca da Lucia. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.
If you’re not ready to end the night just yet, Aurum offers a perfect venue to relax and savor a drink. Similarly, Bar Senza Nome is well-suited for those looking to unwind in a social setting. Caffè Ristretto is another excellent spot to enjoy a nightcap after a delightful meal.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 7
- Bologna - Departure day
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- Church of the Holy Savior
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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 Bologna 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 Chiesa Del Santissimo Salvatore, an eye-catching church before you head out.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Bologna's best shopping area, Quadrilatero. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy. Browse through boutiques to find unique and stylish fashion pieces to take home.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bologna.
Have a fantastic dining experience at Pappare' - Bologna, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Mister Coffee Bistrò offers an enticing alternative with its varied menu.
You’ll then say farewell to Bologna. 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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