4-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south 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 Bologna, Florence, Siena, San Donato in Poggio, San Gimignano, and Lucca.
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 Bologna 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 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 Piazzale Michelangelo are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Della Signoria, learn more about the unique Piazza Del Campo, and immerse yourself in the vibrant atmosphere of Piazza Maggiore.
As you hit the open road and drive through Bologna, Florence, Siena, San Donato in Poggio, San Gimignano, and Lucca, 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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- Piazza Maggiore
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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 1 night 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 Piazza Maggiore, 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 Bologna. 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 Bologna, it's often a good idea to reserve a table in advance.
Enjoy a lovely meal at Ristorante Ciacco, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Ballarini is another top choice with a popular menu. You could also check for a table at Sfoglia Rina. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.
After your meal, keep the night alive at a bar like Bar Al Bricco D'oro, known for its lively atmosphere. Bar Freud E Squisito is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Osteria Del Sole offers an excellent atmosphere for those looking to amp up the evening.
Raise a toast to the start of your 4-day road trip in Italy!
Day 2
- Bologna
- Siena
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Drive 188 km, 3 hours 25 min
- Basilica of Santa Croce in Florence
- piazza della Signoria
- Ponte Vecchio
- Uffizi Gallery
- piazzale Michelangelo
- 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.
Set out on a day brimming with family-friendly attractions, picturesque spots, and historic treasures. Start at the captivating Basilica Of Santa Croce In Florence, a culturally significant church in Bologna. Next, go to Piazza Della Signoria.
After visiting Basilica Of Santa Croce In Florence and Piazza Della Signoria, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Ponte Vecchio. This awe-inspiring historical landmark offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazzale Michelangelo, one of the most history-steeped places to visit in Bologna. If you still have some time left for sightseeing, we also recommend stopping by Piazza Del Campo.
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.
Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. 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 Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 3
- Siena
- Bologna
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Drive 359 km, 5 hours 1 min
- Osservatorio Polifunzionale del Chianti
- Porta San Giovanni
- Walls of Lucca
- Piazza dell'Anfiteatro
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Dive into day 3 of your remarkable road trip in Italy. Today you will explore San Donato in Poggio, San Gimignano, and Lucca, 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 Bologna. You’ll stay here for 1 night.
Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Osservatorio Polifunzionale Del Chianti, an up-and-coming astronomical observatory in the village. Then, head to Porta San Giovanni and soak in the ambiance of this picture-perfect monument.
There are many interesting places to see in Siena, and when you are ready for more, go to Mura Di Lucca. This is one of the village’s most increasingly popular history-steeped spots of interest. After exploring the historical landmark, visit the interesting Piazza Dell'anfiteatro.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna 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 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.
Round off your dining experience by visiting Lime Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Macondo - Cocktail Bar, a bar catering to every mood and preference. Bar Onda Marina By Night likewise offers a unique atmosphere, perfect for a memorable night out.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 4
- Bologna - Departure day
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- Two Towers
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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 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 Two Towers, an instagrammable monument before you head out.
Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones. Discover boutiques offering an array of stylish fashion choices.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bologna.
Treat yourself to a delightful dinner at Va Mo Là, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria dal Biassanot? It's another excellent option with a diverse 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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