11-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, Siena, and Rome
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Explore the best of Italy on a 11-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Rimini, Bologna, Modena, Parma, Florence, Siena, San Gimignano, Greve in Chianti, Rome, and Urbino. 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 Rimini, 2 nights in Bologna, 2 nights in Florence, 2 nights in Siena, and 1 night in Rome. 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. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of Ponte Vecchio.
As you hit the open road and drive through Rimini, Bologna, Modena, Parma, Florence, Siena, San Gimignano, Greve in Chianti, Rome, and Urbino, 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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- Arco di Augusto
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Welcome to Rimini, 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 Rimini's charm before embarking on the next leg of your journey.
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 Arch Of Augustus, 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.
Enjoy a lovely meal at Giusti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Bar Lento is another top choice with a popular menu. You could also check for a table at Amorimini. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rimini tonight.
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 11-day road trip in Italy!
Day 2
- Rimini
- More
Drive 7 km, 58 min
- Cavour Square
- Borgo San Giuliano
- Fountain of the four horses
- Parco Federico Fellini
- La Ruota Panoramica
- Spiaggia libera
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Day 2 of your road trip will take you to the best attractions Rimini has to offer. Cherish the 1 night you have left in Rimini by discovering the best things there are to see and do in the city.
Rimini is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Piazza Cavour, a notable public square that is worthwhile a visit in the city. Nearby, you’ll find Borgo San Giuliano, enchanting visitors with its romantic appeal. Continue your exploration at Fountain Of The Four Horses. This monument is one of the city’s most curiosity-inducing spots.
Enjoy the freedom of exploring Rimini at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Parco Federico Fellini. After exploring the park, head to the up-and-coming La Ruota Panoramica. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Spiaggia Libera, a place of mesmerizing interest in Rimini.
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.
Visit Rimini Centro in Rimini for an unforgettable shopping experience. Browse unique boutiques and stores, each offering delightful surprises. Find unique souvenirs or items to take home, including artisan crafts. After shopping, explore what Rimini Centro has to offer, including attractions, essential services, and vibrant community activities.
As dinnertime approaches, it's time to head out for a bite to eat in Rimini. 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.
Make sure to reserve a table at Osteria Brodo di Giuggiole, an iconic dining spot in Rimini. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Hotel Touring, a popular restaurant in Rimini. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Lo Zodiaco Rimini, a hidden gem nestled in Rimini. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Let the evening flow smoothly from dinner to drinks at Hobo's, a top-rated bar in the area. For other recommendations, Sunflower City Backpacker provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Capogiro offers a memorable night with diverse drink options and excellent service.
Savor another day of unforgettable experiences in Italy!
Day 3
- Rimini
- Bologna
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Drive 120 km, 1 hour 50 min
- Basilica of San Domenico
- Piazza Santo Stefano
- Two Towers
- Bologna Cathedral
- Palazzo Re Enzo
- Piazza Maggiore
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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 Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 2 nights.
Enjoy the perfect balance of relaxation and exploration in Rimini today. One of the most increasingly popular attractions included on the itinerary is Basilica Of San Domenico. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Santo Stefano and learn what makes this visually striking public square unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Two Towers. After exploring the monument, head to Bologna Cathedral. This frequently visited church is a highlight in Rimini. As your day continues, stop by Palazzo Re Enzo, known for its history-steeped features. Lastly, don’t forget to check out the spectacular Piazza Maggiore. Enjoy exploring this incredible public square at your own pace.
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 you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Treat yourself to a delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.
After savoring a delicious meal, step into the vibrant nightlife at Bar Al Bricco D'oro, where the evening is just getting started. In the same way, Bar Freud E Squisito offers a unique charm perfect for experiencing the local bar scene in Bologna. Osteria Del Sole is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 4
- Bologna
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Drive 206 km, 3 hours 9 min
- piazza Grande
- Modena Cathedral
- Torre Civica - Ghirlandina
- Galleria nazionale di Parma
- Palazzo della Pilotta
- Parma Cathedral
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On day 4 of your road trip, you’ll start and end your day in Bologna, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Modena and Parma. You still have 1 night left in Bologna.
Today’s itinerary in Bologna covers several incredible sights, including a public square, a church, a monument, an art gallery, a palace and much more! Start your adventure at Piazza Grande. This frequently visited public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Duomo Di Modena, a must-see church 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 Torre Civica - Ghirlandina. This intriguing monument offers an enriching experience. For a change of pace, head to Galleria Nazionale Di Parma, where you can take in heritage-rich features. Conclude your self-guided sightseeing tour with a visit to Palazzo Della Pilotta and Parma Cathedral. 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 Bologna.
After a day of adventure, treat yourself to an exquisite dinner at one of Bologna's best restaurants.
Treat yourself to a delicious dinner at Bononia Cafè, an excellent option for tonight's dining. Looking for something different? Via Con Me offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Pizzeria La Mela. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.
Keep the evening going at Lime Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Macondo - Cocktail Bar, which offers a similarly pleasant setting and great drinks. Another option is Bar Onda Marina By Night, which provides an inviting environment for unwinding after a busy day out.
Relax and recharge in preparation for another adventurous day in Italy!
Day 5
- Bologna
- Florence
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Drive 111 km, 1 hour 59 min
- Basilica of Santa Croce in Florence
- Bargello National Museum
- Palazzo Vecchio
- Uffizi Gallery
- Ponte Vecchio
- piazza della Signoria
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On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.
Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a church, a museum, a palace, an art gallery, a historical landmark, a public square and much more! Begin your adventure at Basilica Of Santa Croce In Florence. This is a well-known church you should not miss. Another must-see is Bargello National Museum, a worthwhile museum in Bologna.
When you’re ready for the next sight, head to Palazzo Vecchio. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s extraordinary attractions. We recommend continuing your self-guided tour at Ponte Vecchio, a majestic place of interest in the city. If time allows, add Piazza Della Signoria to your itinerary. This spectacular public square offers the perfect finishing touch to your day in Bologna.
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 Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.
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 your glass and celebrate another amazing day of your road trip in Italy!
Day 6
- Florence
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Drive 9 km, 1 hour 21 min
- piazzale Michelangelo
- Cathedral of Santa Maria del Fiore
- Galleria dell'Accademia
- Central Market
- Basilica of Santa Maria Novella
- Oltrarno
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Day 6 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.
Oltrarno is a fantastic place you can explore today in Florence. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Florence-way-of-life and visit all the nearby sights.
Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Piazzale Michelangelo, an astonishing observation deck in the city. Then, head to Cathedral Of Santa Maria Del Fiore and soak in the ambiance of this UNESCO world heritage-listed church.
There are many interesting places to see in Florence, and when you are ready for more, go to Galleria Dell'accademia. This is one of the city’s most popular heritage-rich spots of interest. After exploring the art gallery, visit the well-known Central Market. Not far away, you'll also find Basilica Di Santa Maria Novella, Firenze (fi). This church is an inviting highlight in Florence.
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 delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.
Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 7
- Florence
- Siena
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Drive 77 km, 1 hour 45 min
- Fortezza Medicea
- Basilica of San Domenico
- Siena Cathedral
- Pubblico Palace
- piazza del Campo
- Tower of Mangia
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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 Siena. In the evening, you’ll end up in Siena, where you will stay for 2 nights.
Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, scenic views, and photo-friendly spots. Start at Fortezza Medicea (siena), a locally appreciated monument in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this stunning church.
There are many interesting places to see in Florence, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most captivating inviting spots of interest. After exploring the church, visit the often recommended Pubblico Palace. Not far away, you'll also find Piazza Del Campo. This public square is a history-steeped highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Tower Of Mangia, a worthwhile monument in the city.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 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 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.
After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 8
- Siena
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Drive 154 km, 3 hours 1 min
- Porta San Giovanni
- Piazza del Duomo, San Gimignano
- Town Hall, Picture Gallery and Great Tower
- Chiesa di Sant'Agostino
- Castle of Verrazzano
- Villa Calcinaia - Conti Capponi
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Wake up to day 8 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!
Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most intriguing attractions included on the itinerary is Porta San Giovanni. This UNESCO world heritage-listed monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo and learn what makes this romantic public square unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the up-and-coming Palazzo Comunale, Pinacoteca, Torre Grossa. After exploring the museum, head to Chiesa Di Sant'agostino. This beloved church is a highlight in Siena. As your day continues, stop by Castle Of Verrazzano, known for its history-steeped features. Lastly, don’t forget to check out the increasingly popular Villa Calcinaia - Conti Capponi. Enjoy exploring this incredible winery at your own pace.
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.
Make sure to reserve a table at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo, a hidden gem nestled in Siena. 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 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 9
- Siena
- Rome
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Drive 242 km, 3 hours 37 min
- Colosseum
- Roman Forum
- Trevi Fountain
- Pantheon
- Piazza Navona
- More
Dive into day 9 of your remarkable road trip in Italy. Today you will explore Rome, 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 Rome. You’ll stay here for 1 night.
Today’s agenda in Siena includes an archeological site, a monument, and a public square. Colosseum is must-visit archeological site and a great starting point for the day. Next, continue your journey to Roman Forum, a world-famous archeological site, located just a leisurely stroll away. Next, head to Trevi Fountain, a romantic monument, also available for your discovery today.
Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the iconic Pantheon. If you’re looking for more, Piazza Navona is also a globally renowned attraction that is worthwhile a visit.
When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and spend some time relaxing before you head out to tour the city.
After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.
Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. 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 La Botticella Of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Almalu Trastevere, a bar that offers unique local touches. Likewise, Bar Viminale Di Pepi Maurilio provides an excellent alternative for a fun evening.
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 10
- Rome
- Rimini
- More
Drive 345 km, 4 hours 56 min
- Palazzo Ducale
- National Gallery of the Marche - Ducal Palace of Urbino
- Casa Natale di Raffaello
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Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Urbino. 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.
Savor the day by visiting some of the best places to see in Rome, including a palace and a museum. Start your adventure at Palazzo Ducale. This locally renowned palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Galleria Nazionale Delle Marche located in Rome for another exciting encounter.
Next, immerse yourself in the setting of Casa Santi. Its eye-catching features will captivate you.
At the end of the day, you will drive to Rimini, 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 Rimini's most popular restaurants, and connect with friendly locals for an authentic adventure.
Treat yourself to a wonderful meal at Amarina, a top-rated dining spot in Rimini. If you're in the mood for something new, try Primo Miglio di Conti Mirco, another premier location with a delectable menu. You might also want to book a table at Libeccio. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rimini.
Extend your evening after a delightful meal by visiting Caffè Cavour, which offers the perfect atmosphere for a night out. Moreover, Bar Ilde - Il Baretto Della Buona Piadina is another popular option for a drink or two. Likewise, Bar Malatesta also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Get a good night's sleep and look forward to another great day on the road in Italy!
Day 11
- Rimini - Departure day
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- Malatestiano Temple
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Day 11 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 often recommended church is a popular place to see in the city.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Rimini's best shopping area, Rimini Centro. 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 Rimini.
Treat yourself to a delicious dinner at Ristorante Laura "Darsena Rimini", an excellent option for tonight's dining. Looking for something different? Amerigo offers a tantalizing alternative with its diverse menu. And don’t miss Sabbioni Pizza & Restaurant.
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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