10-Day Italy Road Trip from Bologna traveling west to Milan, Pisa, and Florence

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Explore the best of Italy on a 10-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bologna, Milan, Sarzana, Pisa, and Florence. 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 Bologna, 3 nights in Milan, 1 night in Pisa, and 3 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. Duomo Di Milano Museum and Ponte Vecchio are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Bologna, Milan, Sarzana, Pisa, and Florence, 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

Day 1 – Bologna - arrival day

  • Bologna - Arrival day
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  • Arco Del Meloncello
  • More

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 Arco Del Meloncello or taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Bologna. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

As dinnertime approaches, it's time to head out for a bite to eat in Bologna. 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.

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

Round off your dining experience by visiting Bar Freud E Squisito, a prime location for a drink. Alternatively, explore the distinctive characteristics of Osteria Del Sole, a bar catering to every mood and preference. Macondo - Cocktail Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Raise a toast to the start of your 10-day road trip in Italy!

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Day 2

Day 2 – Bologna, and Milan

  • Milan
  • Bologna
  • More

Drive 223 km, 2 hours 49 min

  • Cattedrale Metropolitana di San Pietro
  • Fontana del Nettuno
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

Dive into day 2 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 Milan. You’ll stay here for 3 nights.

When you’re ready for some sightseeing, make your way to Bologna Cathedral. This much-appreciated catholic cathedral is rated 4.6 out of 5 stars in 3,852 reviews.

Next up is Fountain Of Neptune, Bologna. This fountain has an average rating of 4.7 out of 5 stars from 3,952 visitors.

Another top sightseeing recommendation is Piazza Maggiore. This square has been rated 4.7 out of 5 stars in 64,523 reviews.

Two Towers is another attraction you have the opportunity to visit today. This tower has an average rating of 4.7 out of 5 stars from 25,975 reviews.

To continue your sightseeing, head over to Piazza Santo Stefano. This square is rated an average of 4.8 out of 5 stars in 7,617 reviews.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Milan. Milan offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international, and contemporary dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary, and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Continue your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day in Italy!

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Day 3

Day 3 – Milan

  • Milan
  • More

Drive 1 km, 21 min

  • Teatro alla Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Cathedral Square
  • Palazzo Reale di Milano
  • More

Day 3 of your road trip will take you to the best attractions Milan has to offer. Cherish the 2 nights you have left in Milan by discovering the best things there are to see and do in the city.

When you’re ready for some sightseeing, make your way to La Scala. This much-appreciated opera house is rated 4.7 out of 5 stars in 26,219 reviews.

Next up is Galleria Vittorio Emanuele Ii. This commercial gallery has an average rating of 4.7 out of 5 stars from 91,394 visitors.

Another top sightseeing recommendation is Duomo Di Milano Museum. This art museum has been rated 4.8 out of 5 stars in 138,554 reviews. Every year, 341,609 travelers include this attraction on their travel itinerary.

Cathedral Square is another attraction you have the opportunity to visit today. This sightseeing destination has an average rating of 4.8 out of 5 stars from 7,539 reviews.

To continue your sightseeing, head over to Royal Palace Of Milan. This art museum is rated an average of 4.6 out of 5 stars in 17,538 reviews.

You can learn more about Milan today by going on a tour. Milan offers many top-rated tours and unique experiences that will inspire you. You can browse and select your favorites below.

As you explore more of Milan, 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.

Don’t miss out on dining at Nero 9, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Ristorante la Brisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Milan this evening.

If you’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 4

Day 4 – Milan

  • Milan
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Drive 11 km, 1 hour 16 min

  • Arco della Pace
  • Sempione Park
  • Sforzesco Castle
  • Pinacoteca di Brera
  • Piazza Gae Aulenti
  • More

Day 4 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

An excellent attraction to start your day with is Arch Of Peace. This monument is rated an average of 4.6 out of 5 stars in 27,502 reviews.

Continue your journey at Parco Sempione. This park is rated 4.6 out of 5 stars by 72,914 travelers from near and far.

Milan is also the home of Sforzesco Castle Art Library. This library has an average rating of 4.6 out of 5 stars from 68,714 visitors.

You can continue your self-guided sightseeing tour at Pinacoteca Di Brera. A total of 417 people explore this attraction every year. Rated 4.7 out of 5 stars by 26,077 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Piazza Gae Aulenti. With an average rating of 4.6 out of 5 stars from 30,398 reviews, it’s hard to refuse the opportunity to see this square.

Your discoveries in Milan do not have to stop there. Check out the fantastic selection of tours and tickets offered in Milan on this day of your trip. You can select your tours below.

As dinnertime approaches, it's time to head out for a bite to eat in Milan. 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.

Have a fantastic dining experience at Vento di Sardegna, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Palazzo Parigi Hotel & Grand Spa Milano offers an enticing alternative with its varied menu. Additionally, Galleria Restaurant is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Let the evening flow smoothly from dinner to drinks at Bhangrabar, a top-rated bar in the area. For other recommendations, Rufus Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Ostello Bello Grande offers a memorable night with diverse drink options and excellent service.

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.

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Day 5

Day 5 – Milan, Sarzana, and Pisa

  • Pisa
  • Milan
  • Sarzana
  • More

Drive 295 km, 4 hours 1 min

  • Basilica di Sant'Ambrogio
  • Leonardo da Vinci Museum of Science and Technology
  • Fortezza Firmafede
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Milan, and Sarzana. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Begin your sightseeing with a visit to Basilica Di Sant'ambrogio. This extraordinary church is rated an average of 4.7 out of 5 stars by 12,883 visitors.

Next, make your way to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This top attraction is a technology museum with an average rating of 4.5 out of 5 stars by 22,235 visitors. Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" welcomes 532,084 yearly visitors.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Sarzana. Your travel time is around 2 hours 40 min.

Begin your sightseeing with a visit to Fortezza Di Firmafede. This citadel gets 3,765 visitors each year and is rated an average of 4.4 out of 5 stars in 1,796 reviews.

At the end of the day, you will drive to Pisa, 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 Pisa. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Baribaldi Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Restaurant -Pizzeria Il Mio Capriccio, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Jeffer Cocktails & Friends, a great choice for enjoying the after-dinner hours with a drink. You could also go to Le Parisien Wine Bar, which offers a similarly pleasant setting and great drinks. Another option is Las Volta Cocktailbar, which provides an inviting environment for unwinding after a busy day out.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 6

Day 6 – Pisa, Cascine Vecchie, and Florence

  • Florence
  • Pisa
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Drive 120 km, 1 hour 57 min

  • Piazza dei Cavalieri
  • Leaning Tower of Pisa
  • Piazza del Duomo
  • Cattedrale di Pisa
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
  • More

On day 6 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, and Cascine Vecchie. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Journey into the unknown at Knights' Square, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.5 out of 5 stars from 9,051 reviews.

When you’re ready to continue your sightseeing, Leaning Tower Of Pisa is a recommended place to visit. This bell tower is rated an average of 4.7 out of 5 stars in 116,882 reviews. Based on recent data, the attraction hosts 3,200,000 visitors per year.

Another must-see attraction in Pisa is Piazza Del Duomo, Pisa. Rated an average of 4.7 out of 5 stars by 104,550 travelers, this popular tourist destination in Pisa offers an experience you will remember.

Pisa Cathedral is another popular stop on travelers' itineraries in Pisa. This cathedral promises memorable moments of exploring. Other travelers have rated this attraction 4.8 out of 5 stars in 8,361 reviews.

Set your GPS to Cascine Vecchie and hit the road. Expect a journey of approximately 9 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cascine Vecchie beckons with new experiences!

When you’re ready for some sightseeing, make your way to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This much-appreciated park is rated 4.4 out of 5 stars in 9,632 reviews.

When you’re done exploring for the day, you’ll drive to Florence, where you'll have a hotel waiting for you. Check in and spend some time relaxing before you head out to explore 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 an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative, and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary, and international cuisine in the city.

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, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

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Day 7

Day 7 – Florence

  • Florence
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Drive 3 km, 56 min

  • The Boboli Gardens
  • Ponte Vecchio
  • Uffizi Gallery
  • Palazzo Vecchio
  • Piazza della Signoria
  • More

Day 7 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Your sightseeing of the day begins at The Boboli Gardens, a remarkable park where it’s easy to get lost in exploration. This top attraction is rated an average of 4.2 out of 5 stars in 25,341 reviews.

Next, satisfy your wanderlust at Ponte Vecchio. This deck arch bridge has an average rating of 4.7 out of 5 stars from 118,099 travelers.

Uffizi Gallery is another must-visit attraction. This renowned national museum offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 61,794 travelers and attracting 2,011,219 annual visitors, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Palazzo Vecchio. This well-loved palazzo boasts a 4.7 out of 5-star rating from 19,049 reviews.

When there’s still energy left for exploring, Piazza Della Signoria awaits. If you’ve been interested in experiencing a square, this is a top pick rated 4.8 out of 5 stars by 66,956 previous visitors.

If you have an appetite for more adventure, check out the fantastic selection of tours and tickets offered in Florence on this day of your trip. You'll find the most recommended ones below.

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Enjoy a delicious meal at Trattoria Da Burde, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Ristorante Buca Mario, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Florence this evening.

Raise your glass to another unforgettable day in Italy!

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Day 8

Day 8 – Florence

  • Florence
  • More

Drive 16 km, 1 hour 19 min

  • Parco delle Cascine
  • Accademia Gallery
  • David of Michelangelo
  • Basilica of Santa Croce in Florence
  • Piazzale Michelangelo
  • More

On day 8 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Journey into the unknown at Parco Delle Cascine, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.3 out of 5 stars from 14,875 reviews.

When you’re ready to continue your sightseeing, Galleria Dell'accademia is a recommended place to visit. This national museum is rated an average of 4.6 out of 5 stars in 34,429 reviews. Based on recent data, the attraction hosts 1,719,645 visitors per year.

Another must-see attraction in Florence is David. Rated an average of 4.8 out of 5 stars by 10,476 travelers, this popular tourist destination in Florence offers an experience you will remember.

Basilica Of Santa Croce In Florence is another popular stop on travelers' itineraries in Florence. This church promises memorable moments of exploring. Other travelers have rated this attraction 4.7 out of 5 stars in 28,544 reviews.

Lastly, don't miss out on Piazzale Michelangelo. Rated 4.8 out of 5 stars by 77,744 local and international travelers, it's a popular place to visit.

One of the most unique ways of discovering what else Florence has to offer is by going on a top-rated tour. Be sure to check out all the experiences Florence offers and add your favorites to your Italy travel package 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.

Treat yourself to a delightful dinner at Tijuana, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Djària - American Bar? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Buca Niccolini as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Savor another day of unforgettable experiences in Italy!

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Day 9

Day 9 – Florence, and Bologna

  • Bologna
  • Florence
  • More

Drive 107 km, 2 hours 5 min

  • Cathedral of Santa Maria del Fiore
  • Basilica of Santa Maria Novella
  • Pitti Palace
  • More

On day 9 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 Bologna, where you’ll be staying for 1 night.

Seize the day by visiting some of the best attractions in the area, like Cathedral Of Santa Maria Del Fiore. This extraordinary church has an average rating of 4.8 out of 5 stars from 76,359 visitors.

Next, make your way to Central Market. This point of interest is rated an average of 4.4 out of 5 stars in 43,100 reviews.

While in Florence, we also recommend a visit to Basilica Di Santa Maria Novella, Firenze (fi). This archives has been rated an average of 4.7 out of 5 stars in 23,075 reviews.

If you’re keen to explore even more, then consider a visit to Pitti Palace. This attraction gets around 198,270 yearly visitors. With an average rating of 4.6 out of 5 stars by 23,445 travelers, this art museum is a highly recommended stop on your sightseeing around Florence.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Bologna. Bologna offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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.

Begin your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative, and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Senza Nome, known for its inviting atmosphere. Bar Maurizio is another great option if you’re looking for a place to get the night started. Similarly, Brewdog Bar Bologna provides a great setting to enjoy the night away.

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

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Day 10

Day 10 – Bologna - departure day

  • Bologna - Departure day
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  • Porta Castiglione
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Day 10 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.

On your last day in Italy, take time to indulge in shopping at Bologna’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Kick off the day at Porta Castiglione, a top pick for today’s sightseeing. This city gate is rated an average of 4.4 out of 5 stars in 1,086 reviews.

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

Savor the flavors at Trattoria del Tempo Buono, a top pick for dinner tonight. Alternatively, Cantina Bentivoglio beckons with its unique menu offerings.

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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