One-Week Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, and Siena
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Experience the freedom of the open road in Italy as you embark on an unforgettable 8-day road trip! This experience caters to every traveler, featuring destinations like Rimini, Bologna, 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 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.
Find your way to your hotel in Rimini. 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 Rimini, it's often a good idea to reserve a table in advance.
Savor the flavors at Giusti, a top pick for dinner tonight. Alternatively, Bar Lento beckons with its unique menu offerings. Also, consider Amorimini. With its consistent customer satisfaction, it’s an excellent option for dining in Rimini tonight.
Let the evening flow smoothly from dinner to drinks at Sunflower Beach Backpacker Hostels & Bar, a top-rated bar in the area. For other recommendations, Caffè Il Borgo provides a perfect setting for rounding out your night with style and great drinks. Likewise, Primo Bacio Città Lounge Bar offers a memorable night with diverse drink options and excellent service.
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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On day 2 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 Rimini and Bologna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.
Today’s itinerary in Rimini covers several incredible sights, including a monument, a park, an art gallery, a museum, a public square and much more! Start your adventure at Arch Of Augustus. This well-known monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Parco Federico Fellini, a must-see park in the city.
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 Pinacoteca Nazionale Di Bologna. This often recommended art gallery offers an enriching experience. For a change of pace, head to Two Towers, where you can take in breathtaking features. Conclude your self-guided sightseeing tour with a visit to International Museum And Library Of Music and Piazza Santo Stefano. These sights offer a fulfilling end to a perfect day.
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.
After a day of adventure, treat yourself to an exquisite dinner at one of Bologna's best restaurants.
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.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing 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
- 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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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.
Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and photo-friendly spots. 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. Palazzo D'accursio is the first of them. Spend some time admiring this breathtaking palace before continuing your journey. Piazza Maggiore is your next stop. This spectacular public square 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 Biblioteca Salaborsa. This photogenic library is a sight to behold. To round off your sightseeing experience, visit Bologna Cathedral and Fountain Of Neptune, Bologna. If time allows, end your day with Palazzo Re Enzo, a historic palace 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 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 Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.
To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.
Savor another day of unforgettable experiences 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.
Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Piazzale Michelangelo, an extraordinary observation deck in the city. Then, head to Ponte Vecchio and soak in the ambiance of this romantic historical landmark.
There are many interesting places to see in Florence, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most extraordinary historic spots of interest. After exploring the art gallery, visit the locally renowned Palazzo Vecchio. Not far away, you'll also find Piazza Della Signoria. This public square is a visually striking highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Cathedral Of Santa Maria Del Fiore, a widely recognized church in the city.
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 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.
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.
Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.
Raise your glass and celebrate another amazing day of your road trip 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.
Today’s route brings family-friendly attractions, breathtaking views, and picturesque spots. The first attraction of today is Fortezza Medicea (siena). This underrated monument is a culturally significant place to see in Florence. Continue your discovery at Basilica Of San Domenico, a historic church with stories to tell.
As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Fontebranda. This intriguing historical landmark offers an eye-catching encounter with Florence. Next, make your way to Siena Cathedral to add another highlight to your day. After that, visit Pubblico Palace, an up-and-coming palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Del Campo, a top-rated public square in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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.
Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.
Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.
As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in 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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On day 6 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.
Today’s itinerary in Siena covers several incredible sights, including a museum and a public square. Start your adventure at Sangimignano1300. This worthwhile 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 increasingly popular 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.
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 Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.
After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Get a good night's sleep and look forward to another great day on the road 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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Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Pisa. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rimini. You will spend 1 night here for some well-deserved relaxation.
Get ready to discover some of the most iconic wonders in Siena, including a public square, a monument, and a church. Start your day at Knights' Square. This breathtaking public square is a curiosity-inducing place to see in Siena. Then, wander over to Leaning Tower Of Pisa. If picture-perfect sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Del Duomo, Pisa. This breathtaking public square is a favorite among visitors.
Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pisa Cathedral is a worthwhile spot in the city that will captivate you with its unique charm.
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.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rimini. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Enjoy a delicious meal at Osteria Brodo di Giuggiole, a top-rated dining destination in Rimini. If you're in the mood to try something new, consider Hotel Touring, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Lo Zodiaco Rimini. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rimini this evening.
Unwind after your meal by stepping into Hobo's. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Sunflower City Backpacker offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Capogiro, another top-rated bar in the area.
Celebrate another amazing day of your road trip adventure in Italy!
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, begin at Malatestiano Temple. This locally appreciated church is a popular place to see in the city.
Make the most of your final day in Italy by visiting Rimini’s iconic markets and shopping establishments in the buzzing Rimini Factory Outlet. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Rimini.
If you're eager to try something different, consider Primo Miglio di Conti Mirco, another top spot with a tantalizing 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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