7-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Florence and San Gimignano

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Photo of panoramic view of Bologna,Italy.
Photo of Channel river in Bologna Italy.
Photo of Fontana di Nettuno or Neptune fountain on Piazza Maggiore square at the morning dusk designed by Tommaso Laureti (1565).
Photo of Bologna main square aerial view from Asinelli tower.
Photo of ancient sanctuary of the Madonna di San Luca, old church on the hill.
Photo of quirky castle in the Emilian Apennines, Bologna, Italy.
Photo of Basilica of SantApolinare in Classe.
Photo of View of Basilica di San Petronio on sunrise.
Photo of Sunset view of a small lake located in a park in the center of Bologna, Italy.
Bologna, Italy. View of Basilica di San Petronio on sunrise
Palazzo Re Enzo. Splendid cityscape of Bologna, Italy.
photo of view of Bologna, Italy.
Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
photo of view of Florence,Italy.
photo of view of Florence,Italy.
Photo of Historic center in San Gimignano in Italy by Makalu
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Explore the best of Italy on a 7-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bologna, Florence, Siena, San Gimignano, Pisa, Lucca, Greve in Chianti, and Gaiole in Chianti. 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 Bologna, 2 nights in Florence, and 1 night in San Gimignano. 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, San Gimignano, Pisa, Lucca, Greve in Chianti, and Gaiole in Chianti, 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
arco del Meloncello
Pinacoteca Nazionale di BolognaTwo TowersPiazza Santo StefanoPiazza MaggioreBologna CathedralFountain of Neptune, Bologna
piazzale MichelangeloBasilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioPalazzo VecchioCathedral of Santa Maria del Fiore
Fortezza MediceaBasilica of San DomenicoTower of Mangiapiazza del CampoSiena CathedralPiazza del Duomo, San Gimignano
Pisa CathedralPiazza del Duomo, PisaLeaning Tower of PisaWalls of LuccaPiazza dell'Anfiteatro
Castle of VerrazzanoCastello di BrolioCapannelle
Church of the Holy Savior

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Day 1

Day 1

  • Bologna - Arrival day
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  • arco del Meloncello
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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 2 nights 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 just 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. 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 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.

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

Raise a toast to the start of your 7-day road trip in Italy!

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Day 2

Day 2

  • Bologna
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Drive 3 km, 42 min

  • Pinacoteca Nazionale di Bologna
  • Two Towers
  • Piazza Santo Stefano
  • Piazza Maggiore
  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • More

Day 2 of your road trip across Italy promises a magnificent time exploring Bologna. You have 1 night left in Bologna. Take the opportunity to experience more of the best attractions and activities in the city.

Set out on a day brimming with fun adventures, picturesque spots, and history-rich sites. Start at the often recommended Pinacoteca Nazionale Di Bologna, a visually striking art gallery in Bologna. Next, go to Two Towers.

After visiting Pinacoteca Nazionale Di Bologna and Two Towers, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Piazza Santo Stefano. This romantic public square offers a unique experience. Piazza Maggiore is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Bologna Cathedral, one of the most culturally significant places to visit in Bologna. If you still have some time left for sightseeing, we also recommend stopping by Fountain Of Neptune, Bologna.

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.

Experience shopping bliss at Bologna as you explore Via d'Azeglio. Take a leisurely stroll through unique boutiques and high-end shops, where local treasures are waiting to be found. Beyond shopping, Via d'Azeglio offers more options, including unique attractions, key services, and vibrant events.

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

Enjoy a delicious meal at Bononia Cafè, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Via Con Me, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

Round off your dining experience by visiting Lime Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Macondo - Cocktail Bar, a bar catering to every mood and preference. Bar Onda Marina By Night likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

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Day 3

Day 3

  • Bologna
  • Florence
  • More

Drive 118 km, 2 hours 20 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Palazzo Vecchio
  • Cathedral of Santa Maria del Fiore
  • More

On day 3 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 1 night.

Today’s agenda in Bologna includes an observation deck, a church, an art gallery, a historical landmark, a palace and much more! Piazzale Michelangelo is must-visit observation deck and a great starting point for the day. Next, continue your journey to Basilica Of Santa Croce In Florence, a notable church, located just a leisurely stroll away. Next, head to Uffizi Gallery, a historic art gallery, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bologna. When you're ready, let your sightseeing route take you to the world-famous Ponte Vecchio. If you’re looking for more, Palazzo Vecchio is also a popular attraction that is worthwhile a visit. Lastly, don’t miss Cathedral Of Santa Maria Del Fiore, a place of inviting interest 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 Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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.

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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 4

Day 4

  • Florence
  • San Gimignano
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Drive 121 km, 2 hours 28 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Tower of Mangia
  • piazza del Campo
  • Siena Cathedral
  • Piazza del Duomo, San Gimignano
  • 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 Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in San Gimignano, which will be your home away from home for 1 night.

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Florence. Begin your sightseeing with Fortezza Medicea (siena). This frequently visited monument is one of the top attractions in the city. Proceed to Basilica Of San Domenico, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Tower Of Mangia. This increasingly popular monument is a traveler-favorite. Not far away, you’ll find Piazza Del Campo, another key site on your sightseeing itinerary. Siena Cathedral is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Duomo and uncover why it's recognized as one of the city's most often recommended attractions.

At the end of the day, you will drive to San Gimignano, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

Savor another day of unforgettable experiences in Italy!

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Day 5

Day 5

  • San Gimignano
  • Florence
  • More

Drive 193 km, 3 hours 25 min

  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Walls of Lucca
  • Piazza dell'Anfiteatro
  • 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 - Pisa and Lucca. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Get ready for a day filled with fun adventures, breathtaking views, and picturesque spots in the charming city of San Gimignano. Your adventure starts at Pisa Cathedral, an up-and-coming local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This world-famous public square is known for its grand appeal.

After soaking in the highlights of these sights, take some time to wander San Gimignano's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This culturally significant monument offers a fascinating experience that many visitors find memorable. Mura Di Lucca is also worth visiting, along with Piazza Dell'anfiteatro. These standout landmarks offer unique experiences that add to the day’s enjoyment.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour 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 a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 6

Day 6

  • Florence
  • Bologna
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Drive 249 km, 4 hours 18 min

  • Castle of Verrazzano
  • Castello di Brolio
  • Capannelle
  • More

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Greve in Chianti, San Regolo, and Gaiole in Chianti. When you’re not sightseeing, take time to relax at your selected hotel in Bologna, where you’ll be staying for 1 night.

Get ready to discover some of the most iconic wonders in Florence, including a castle and a winery. Start your day at Castle Of Verrazzano. This respected castle is an underrated place to see in Florence. Then, wander over to Castello Di Brolio. If visually striking sites excite you, this castle will be right up your alley. Nearby, you’ll also find Capannelle. This romantic winery is a favorite among visitors.

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.

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.

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. And don’t miss Ristorante Enoteca da Lucia. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Continue the enjoyment post-dinner at Aurum, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Senza Nome offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffè Ristretto. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 7

Day 7

  • Bologna - Departure day
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  • Church of the Holy Savior
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Day 7 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 Chiesa Del Santissimo Salvatore. This up-and-coming church 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 Via d'Azeglio. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. You can also browse through boutiques for stylish fashion choices. 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.

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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