5-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Florence

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Experience the freedom of the open road in Italy as you embark on an unforgettable 5-day road trip! This experience caters to every traveler, featuring destinations like Bologna, Florence, Siena, Pisa, and Lucca.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Bologna and 2 nights in Florence. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Bologna, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Ponte Vecchio and 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 Bologna, Florence, Siena, Pisa, and Lucca, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Piazza Maggiore
piazzale MichelangeloBasilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioCathedral of Santa Maria del Fiorepiazza della Signoria
Fortezza MediceaBasilica of San DomenicoSiena Cathedralpiazza del CampoTower of MangiaPubblico Palace
Piazza del Duomo, PisaLeaning Tower of PisaWalls of LuccaSan Michele in ForoPiazza dell'Anfiteatro
Two Towers

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Day 1

Day 1

  • Bologna - Arrival day
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  • Piazza Maggiore
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Welcome to Bologna, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night immersing yourself in Bologna's charm before embarking on the next leg of your journey.

Bologna is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Piazza Maggiore, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Bologna. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Bologna, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Ristorante Ciacco, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Ristorante Ballarini, another top spot with a mouthwatering menu. You might also want to secure a reservation at Sfoglia Rina. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

Raise a toast to the start of your 5-day road trip in Italy!

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Day 2

Day 2

  • Bologna
  • Florence
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Drive 118 km, 2 hours 19 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Bologna, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Piazzale Michelangelo, an extraordinary observation deck in the city. Then, head to Basilica Of Santa Croce In Florence and soak in the ambiance of this culturally significant church.

There are many interesting places to see in Bologna, and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most famous romantic spots of interest. After exploring the art gallery, visit the world-famous Ponte Vecchio. Not far away, you'll also find Cathedral Of Santa Maria Del Fiore. This church is a grand highlight in Bologna. Before wrapping up your self-guided sightseeing tour, head to Piazza Della Signoria, an extraordinary public square in the city.

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 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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Say good night to Florence and look forward to another great day of your road trip in Italy!

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Day 3

Day 3

  • Florence
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Drive 154 km, 2 hours 53 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Pubblico Palace
  • More

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, scenic views, and picturesque spots. Start at Fortezza Medicea (siena), an increasingly popular monument in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this majestic 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 popular enchanting spots of interest. After exploring the church, visit the astonishing Piazza Del Campo. Not far away, you'll also find Tower Of Mangia. This monument is an UNESCO world heritage-listed highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Pubblico Palace, a locally appreciated palace in the city.

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

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

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 4

Day 4

  • Florence
  • Bologna
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Drive 260 km, 3 hours 58 min

  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Walls of Lucca
  • San Michele in Foro
  • Piazza dell'Anfiteatro
  • More

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Lucca. 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 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a public square, a monument, a historical landmark, a church and much more! Begin your adventure at Piazza Del Duomo, Pisa. This is a world-famous public square you should not miss. Another must-see is Leaning Tower Of Pisa, a world-famous monument in Florence.

When you’re ready for the next sight, head to Mura Di Lucca. From there, take a leisurely stroll to San Michele In Foro, another of the city’s curiosity-inducing attractions. We recommend continuing your self-guided tour at Piazza Dell'anfiteatro, a romantic place of interest in the city.

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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Bologna. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely meal at Bononia Cafè, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Via Con Me is another top choice with a popular menu. You could also check for a table at Trattoria Pizzeria La Mela. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

Continue your lively evening at Lime Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Macondo - Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Onda Marina By Night ensures a night out tailored to your taste.

Relax and recharge in preparation for another adventurous day in Italy!

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Day 5

Day 5

  • Bologna - Departure day
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  • Two Towers
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Day 5 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Bologna before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, begin at Two Towers. This captivating monument is a popular place to see in the city.

Make the most of your final day in Italy by visiting Bologna’s iconic markets and shopping establishments in the buzzing Galleria Cavour. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. Elevate your style with pieces from high-end retail stores.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bologna.

If you're in the mood to try something new, consider Trattoria dal Biassanot, another top spot with a mouthwatering menu.

You’ll then say farewell to Bologna. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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