One-Week Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, and Siena

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Escape the ordinary with this exciting 8-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

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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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Cavour Square
Arco di AugustoParco Federico FelliniPinacoteca Nazionale di BolognaTwo TowersInternational Museum and Library of MusicPiazza Santo Stefano
Palazzo d'AccursioPiazza MaggioreBiblioteca SalaborsaBologna CathedralFountain of Neptune, BolognaPalazzo Re Enzo
piazzale MichelangeloPonte VecchioUffizi GalleryPalazzo Vecchiopiazza della SignoriaCathedral of Santa Maria del Fiore
Fortezza MediceaBasilica of San DomenicoFontebrandaSiena CathedralPubblico Palacepiazza del Campo
SanGimignano1300Town Hall, Picture Gallery and Great TowerPiazza del Duomo, San Gimignano
Knights' SquareLeaning Tower of PisaPiazza del Duomo, PisaPisa Cathedral
Malatestiano Temple

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Day 1

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.

Don’t miss out on dining at Giusti, a top-rated dining destination in Rimini. If you're in the mood to try something new, consider Bar Lento, another top spot with a mouthwatering menu. You might also want to secure a reservation at Amorimini. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rimini this evening.

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!

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Day 2

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
  • More

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 route brings fun adventures, photo-friendly spots, and historic treasures. The first attraction of today is Arch Of Augustus. This popular monument is a heritage-rich place to see in Rimini. Continue your discovery at Parco Federico Fellini, an eye-catching park with stories to tell.

As you stroll around Rimini, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pinacoteca Nazionale Di Bologna. This worthwhile art gallery offers an instagrammable encounter with Rimini. Next, make your way to Two Towers to add another highlight to your day. After that, visit International Museum And Library Of Music, an increasingly popular museum that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Santo Stefano, a worthwhile 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 Rimini.

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.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 3

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
  • More

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Palazzo D'accursio. This intriguing palace provides an insightful glimpse into the city's identity. Next, discover Piazza Maggiore, a symbolic public square, promising a delightful encounter.

Continue your sightseeing with a visit to Biblioteca Salaborsa, an underrated library. When you’re done, don’t forget to make a stop at the worthwhile Bologna Cathedral. Not far away from the church, you will find the instagrammable Palazzo Re Enzo, perfect for a quick visit. Round off your day at Fountain Of Neptune, Bologna, another gem in Bologna with symbolic features to discover.

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.

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 delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

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Day 4

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
  • More

Day 4 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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This visually striking observation deck is sure to ignite your curiosity. Next, dive into the grand features of Ponte Vecchio, a must-visit historical landmark in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Uffizi Gallery, an impressive art gallery. For a change of scene, check out Palazzo Vecchio, known for its enchanting features. We also recommend visiting Piazza Della Signoria. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Cathedral Of Santa Maria Del Fiore, yet another famous attraction 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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 5

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
  • More

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 family-friendly attractions, breathtaking views, and picturesque spots! Start at Fortezza Medicea (siena), an underrated monument that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of San Domenico, enchanting visitors with its breathtaking 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 locally appreciated Pubblico Palace. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Del Campo, a place of history-steeped interest in Florence.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and spend some time relaxing before you head out to tour the city.

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.

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip in Italy!

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Day 6

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
  • More

On day 6 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Prepare for a day full of family-friendly attractions, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Sangimignano1300. This often recommended museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Palazzo Comunale, Pinacoteca, Torre Grossa, one of the village’s best highlights.

Next, check out Piazza Del Duomo, one of the most frequently visited places to see in Siena. This public square is a favorite among locals and travelers alike.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

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 Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub 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.

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Day 7

Day 7

  • Siena
  • Rimini
  • More

Drive 420 km, 5 hours 8 min

  • Knights' Square
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • More

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Pisa. When you’re not sightseeing, take time to relax at your selected hotel in Rimini, where you’ll be staying 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 Knights' Square, a locally appreciated public square in the city. Then, head to Leaning Tower Of Pisa and soak in the ambiance of this UNESCO world heritage-designated monument.

There are many interesting places to see in Siena, and when you are ready for more, go to Piazza Del Duomo, Pisa. This is one of the city’s most timeless historic spots of interest. After exploring the public square, visit the increasingly popular Pisa Cathedral.

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.

Indulge in a memorable dining experience at one of Rimini's most popular restaurants, and connect with friendly locals for an authentic adventure.

Savor the flavors at Osteria Brodo di Giuggiole, a top pick for dinner tonight. Alternatively, Hotel Touring beckons with its unique menu offerings. Also, consider Ristorante Lo Zodiaco Rimini. With its consistent customer satisfaction, it’s an excellent option for dining in Rimini tonight.

Keep the excitement of the evening going by visiting a bar or two. Hobo's is an excellent place to start. You could also check out Sunflower City Backpacker, offering a different kind of charm. A last recommendation for the day is Bar Capogiro. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

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Day 8

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 photogenic church before you head out.

Maximize your last day in Italy and go on a shopping spree in Rimini’s shopping center, the lively Rimini Centro. Browse for souvenirs to remind you of your wonderful journey in Italy. Discover boutiques with stylish fashion choices to upgrade your wardrobe.

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 in the mood to try something new, consider Primo Miglio di Conti Mirco, another top spot with a mouthwatering 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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