One-Week Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, and Siena
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Explore the best of Italy on a 8-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Rimini, Bologna, Florence, Siena, San Gimignano, and Pisa. 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 Rimini, 1 night in Bologna, 2 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 Rimini, 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 Rimini, Bologna, 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
- Rimini - Arrival day
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- Cavour Square
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Say hello to Rimini! 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 Rimini for 1 night before you continue your adventure!
Rimini 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 Cavour, 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 Rimini. 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 Rimini, it's often a good idea to reserve a table in advance.
Have a fantastic dining experience at Giusti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Bar Lento offers an enticing alternative with its varied menu. Additionally, Amorimini is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rimini.
Continue your lively evening at Sunflower Beach Backpacker Hostels & Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Caffè Il Borgo is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Primo Bacio Città Lounge Bar ensures a night out tailored to your taste.
Raise a toast to the start of your 8-day road trip in Italy!
Day 2
- Rimini
- Bologna
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Drive 123 km, 2 hours 4 min
- Arco di Augusto
- Parco Federico Fellini
- Pinacoteca Nazionale di Bologna
- Two Towers
- International Museum and Library of Music
- Piazza Santo Stefano
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Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Rimini and Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.
Rimini is brimming with adventures. Today’s wonderful stops include a monument, a park, an art gallery, a museum, a public square and much more! Begin your sightseeing adventure at the notable Arch Of Augustus and allow yourself time to explore. Just a short distance away you'll find your next stop, Parco Federico Fellini, a romantic park that draws visitors from far and near.
Continue your journey to Pinacoteca Nazionale Di Bologna, one of the city’s most intriguing spots that you shouldn’t miss. Another great site to visit is the popular Two Towers. When you're finished at the monument, International Museum And Library Of Music awaits your visit. This museum is a respected highlight on today's itinerary. Last up is a public square - the often recommended Piazza Santo Stefano.
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.
As you explore more of Bologna, 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.
Make sure to reserve a table at Ristorante Ciacco, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Ballarini, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sfoglia Rina, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Al Bricco D'oro, known for its inviting atmosphere. Bar Freud E Squisito is another great option if you’re looking for a place to get the night started. Similarly, Osteria Del Sole provides a great setting to enjoy the night away.
Head back to your accommodation in Bologna and get some rest in preparation for another magical day of your road trip in Italy!
Day 3
- Bologna
- Florence
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Drive 120 km, 1 hour 45 min
- Palazzo d'Accursio
- Piazza Maggiore
- Biblioteca Salaborsa
- Bologna Cathedral
- Fountain of Neptune, Bologna
- Palazzo Re Enzo
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Dive into day 3 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Florence. You’ll stay here for 2 nights.
Brace yourself for today’s incredible lineup of attractions in Bologna, featuring family-friendly attractions, breathtaking views, and photo-friendly spots. Start at Palazzo D'accursio, an up-and-coming palace in the city. Then, head to Piazza Maggiore and soak in the ambiance of this history-steeped public square.
There are many interesting places to see in Bologna, and when you are ready for more, go to Biblioteca Salaborsa. This is one of the city’s most increasingly popular history-steeped spots of interest. After exploring the library, visit the up-and-coming Bologna Cathedral. Not far away, you'll also find Fountain Of Neptune, Bologna. This monument is a symbolic highlight in Bologna. Before wrapping up your self-guided sightseeing tour, head to Palazzo Re Enzo, an often recommended palace in the city.
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.
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.
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.
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.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 4
- Florence
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Drive 4 km, 1 hour 5 min
- piazzale Michelangelo
- Ponte Vecchio
- Uffizi Gallery
- Palazzo Vecchio
- piazza della Signoria
- Cathedral of Santa Maria del Fiore
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Day 4 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Florence 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 visually striking observation deck before continuing your journey. Ponte Vecchio is your next stop. This timeless historical landmark is one of the best-rated sights in Florence.
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 historic art gallery is a sight to behold. To round off your sightseeing experience, visit Palazzo Vecchio and Piazza Della Signoria. If time allows, end your day with Cathedral Of Santa Maria Del Fiore, an enchanting church that offers a memorable conclusion to your exploration.
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.
Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.
Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.
Savor another day of unforgettable experiences in Italy!
Day 5
- Florence
- Siena
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Drive 77 km, 1 hour 44 min
- Fortezza Medicea
- Basilica of San Domenico
- Fontebranda
- Siena Cathedral
- Pubblico Palace
- piazza del Campo
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Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of 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 2 nights.
Florence is home to plenty of attractions that offer fun adventures, breathtaking views, and picturesque spots! Start at Fortezza Medicea (siena), a frequently visited monument that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of San Domenico, enchanting visitors with its stunning appeal. Continue your exploration at Fontebranda. This historical landmark is one of the city’s most increasingly popular spots.
Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Siena Cathedral. After exploring the church, head to the often recommended Pubblico Palace. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Del Campo, a place of visually striking interest in Florence.
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.
Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.
Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.
To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.
Savor another day of unforgettable experiences in Italy!
Day 6
- Siena
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Drive 82 km, 1 hour 40 min
- SanGimignano1300
- Town Hall, Picture Gallery and Great Tower
- Piazza del Duomo, San Gimignano
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Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena 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 San Gimignano.
Today’s itinerary in Siena covers several incredible sights, including a museum and a public square. Start your adventure at Sangimignano1300. This up-and-coming museum is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Palazzo Comunale, Pinacoteca, Torre Grossa, a must-see museum in the village.
Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Piazza Del Duomo. This up-and-coming public square offers an enriching experience. These sights offer a fulfilling end to a perfect day.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Siena.
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.
Celebrate another amazing day of your road trip adventure in Italy!
Day 7
- Siena
- Rimini
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Drive 420 km, 5 hours 8 min
- Knights' Square
- Leaning Tower of Pisa
- Piazza del Duomo, Pisa
- Pisa Cathedral
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On day 7 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. In the evening, you’ll end up in Rimini, 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 city of Siena. Your adventure starts at Knights' Square, an underrated local hot spot. Another notable attraction to explore is Leaning Tower Of Pisa. This world-famous monument is known for its respected 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 Piazza Del Duomo, Pisa. This stunning public square offers a fascinating experience that many visitors find memorable. Pisa Cathedral is also worth visiting.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rimini. Rimini offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rimini. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Enjoy a delicious meal at Osteria Brodo di Giuggiole, a highly-rated dining destination in Rimini. If you're eager to try something different, consider Hotel Touring, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Lo Zodiaco Rimini. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rimini this evening.
Explore the vibrant nightlife at Hobo's after your meal, a hub for lively evenings and memorable moments. Or, head to Sunflower City Backpacker for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Capogiro is perfect for those looking to extend their night with a touch of local flavor.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 8
- Rimini - Departure day
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- Malatestiano Temple
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Day 8 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Rimini 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 Malatestiano Temple, a culturally significant church 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 Rimini.
Have a fantastic dining experience at Amarina, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Primo Miglio di Conti Mirco offers an enticing alternative with its varied menu.
You’ll then say farewell to Rimini. 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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