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Road trips in Italy

3-Day Italy Self-Drive Road Trip With Itinerary Starting in Bologna

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Photo of panoramic view of Bologna,Italy.

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Explore the best of Italy on a remarkable 3-day road trip! Combine exploration with relaxation on a self-drive tour featuring Bologna, Florence, and San Gimignano.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Bologna. 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 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 Piazzale Michelangelo are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Bologna, Florence, and San Gimignano, 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, accommodations, 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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Day1

Day 1

Bologna - Arrival day
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Piazza Maggiore
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Your road trip adventure in Italy begins as soon as you reach Bologna and pick up your car. You’ll stay here for 2 nights and explore what to see in Bologna, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Bologna. Make yourself at home and unwind 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 Bologna, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Ristorante Ciacco, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Ballarini? It's another excellent option with a diverse menu. Consider reserving a table at Sfoglia Rina as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

Extend your evening after a delightful meal by visiting Bar Al Bricco D'oro, which offers the perfect atmosphere for a night out. Moreover, Bar Freud E Squisito is another popular option for a drink or two. Likewise, Osteria Del Sole also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise a toast to the start of your 3-day road trip in Italy!

Day2

Day 2

Bologna
Florence
San Gimignano
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Drive 312 km, 4 hours 58 min

Cathedral of Santa Maria del Fiore
Ponte Vecchio
Uffizi Gallery
piazzale Michelangelo
Porta San Giovanni
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On day 2 of your road trip, you’ll start and end your day in Bologna, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Florence and San Gimignano.

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Florence. Expect your car journey to take a minimum of 1 hour 33 min. When you arrive in Florence, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Cathedral Of Santa Maria Del Fiore and explore the UNESCO world heritage-designated features. Next, make your way to Ponte Vecchio, another highlight in Florence. When you’re done exploring the historical landmark, continue to Uffizi Gallery, a picture-perfect art gallery.

Nearby, you will also find Piazzale Michelangelo. This widely recognized observation deck is a top place to see in the area.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Gimignano may take around 51 min. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Porta San Giovanni, an often recommended monument that everyone visiting San Gimignano should see.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Bologna.

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 Bononia Cafè, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Via Con Me, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

After your meal, keep the night alive at a bar like Lime Bar, known for its lively atmosphere. Macondo - Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Onda Marina By Night offers an excellent atmosphere for those looking to amp up the evening.

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

Day3

Day 3

Bologna - Departure day
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Two Towers
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Day 3 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, we recommend visiting Two Towers, a culturally significant monument before you head out.

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 vacation. 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.

Treat yourself to a delicious dinner at Va Mo Là, an excellent option for tonight's dining. Looking for something different? Trattoria dal Biassanot offers a tantalizing alternative with its diverse 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!

How it works

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Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

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