Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Florence to Bologna, Venice, and Milan

On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, where you'll stay for 1 night, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Florence, and meet locals along the way!

Make time for Piazza Della Signoria, an impressive public square that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its romantic appeal. Continue your exploration at Ponte Vecchio. This historical landmark is one of the city’s most timeless 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 Pitti Palace. After exploring the palace, head to the notable The Boboli Gardens.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Florence. There are so many fun and eye-opening activities to try out in Florence that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Florence to find the best options for you!

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

Day 3 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Florence and end it in Bologna. You’ll stay in Bologna for 3 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Experience Basilica Of Santa Croce In Florence, a notable church in the city. Then, head to Galleria Dell'accademia and soak in the ambiance of this instagrammable art gallery.

There are many interesting places to see in Florence, and when you are ready for more, go to Cathedral Of Santa Maria Del Fiore. This is one of the city’s most astonishing history-steeped spots of interest. After exploring the church, visit the captivating Basilica Di Santa Maria Novella, Firenze (fi).

In Bologna, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Have a memorable dining experience in Bologna by booking a table at Ahimè, a Bib Gourmand restaurant presenting an exceptional country cooking menu. For a different culinary experience in Bologna, I Portici shines as one of the top destinations, known for its delicious creative and contemporary cuisine. This 1-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Trattoria di Via Serra is known as a top local spot in Bologna for its delicious emilian cuisine. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

If you feel like it, head out to a bar to celebrate another fantastic day in Bologna and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

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.

Savor the rest of the night and celebrate another incredible, relaxed road trip adventure in the magical Bologna!

Day 4 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Bologna!

Catch Palazzo Re Enzo before the crowds roll in. This instagrammable palace is sure to ignite your curiosity. Next, dive into the noteworthy features of Fountain Of Neptune, Bologna, a must-visit monument 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 Piazza Maggiore, a famous public square. For a change of scene, check out Bologna Cathedral, known for its respected features. We also recommend visiting Chiesa Del Santissimo Salvatore. This church is a must for anyone looking to experience the city to the fullest.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Bologna offers a wide selection of experiences for every traveler.

Exploring new places makes you hungry. Luckily, Bologna has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Treat yourself to a wonderful meal at Bononia Cafè, a top-rated dining spot in Bologna. If you're in the mood for something new, try Via Con Me, another premier location with a delectable menu. You might also want to book a table at Trattoria Pizzeria La Mela. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

Experience the amazing nightlife in Bologna and unwind at the coolest bars in the city.

To truly maximize your evening out, consider visiting Lime Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Macondo - Cocktail Bar, another bar with an inviting ambiance. Similarly, Bar Onda Marina By Night also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

Day 5 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Enjoy all that Two Towers has to offer. This is a well-known monument you should not miss. Another must-see is Piazza Santo Stefano, a worthwhile public square in Bologna.

When you’re ready for the next sight, head to Porta Castiglione. From there, take a leisurely stroll to Arco Del Meloncello, another of the city’s worthwhile attractions. We recommend continuing your self-guided tour at Ducati Museum, a heritage-rich place of interest in the city.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Exploring the food culture in Bologna offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Make sure to reserve a table at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

Unwind after your meal by stepping into Aurum. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Senza Nome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Ristretto, another top-rated bar in the area.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

Day 6 of your relaxed road trip in Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

Awaiting your discovery is the often recommended San Martino, a culturally significant church in Bologna. Next, go to La Piccola Venezia.

After visiting San Martino and La Piccola Venezia, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Porta Galliera. This culturally significant monument offers a unique experience. Faizan-e-madina Bologna is another noteworthy attraction worthwhile a visit.

Continue your laid-back road trip in Italy as you make your way to Venice. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Experience a symphony of flavors at Local in Venice by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Local delights its guests with its exceptional variety of meals showcasing delicious contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Wistèria, acclaimed for its delectable contemporary and venetian specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Quadri, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for modern cuisine in the city.

Experience the amazing nightlife in Venice and unwind at the coolest bars in the city.

Continue your lively evening at Al Parlamento, a perfect place for winding down or revving up the night, depending on which mood you’re in. The Caffe Rosso is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Adagio ensures a night out tailored to your taste.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

On day 7 of your leisurely self-drive tour across Italy, you’ll go deep into Venice, where you'll stay for 3 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Venice, and meet locals along the way!

Venice is brimming with adventures.

Experience Piazza San Marco, a world-famous public square in the city. Then, head to St Mark's Campanile and soak in the ambiance of this UNESCO world heritage-designated monument.

There are many interesting places to see in Venice, and when you are ready for more, go to St Mark's Basilica. This is one of the city’s most interesting majestic spots of interest. After exploring the church, visit the well-known Doge's Palace. Not far away, you'll also find Bridge Of Sighs. This monument is a majestic highlight in Venice.

Italy makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Venice, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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

Before calling it a day, visit one of the best bars in Venice. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Let the evening flow smoothly from dinner to drinks at Il Mercante, a top-rated bar in the area. For other recommendations, The Irish Pub Venezia provides a perfect setting for rounding out your night with style and great drinks. Likewise, Ai Stagneri offers a memorable night with diverse drink options and excellent service.

Cherish every minute of your relaxed road trip vacation across Italy.

Day 8 of your relaxed road trip through Italy means 24 hours of making the best memories in Lido. You’ll go sightseeing at famous attractions in Lido. In the evening, you will experience one of the most popular dining spots in the town. So buckle up and prepare to be blown away by Lido!

Make a stop at Venetian Arsenal. This worthwhile historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Teatro La Fenice located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Palazzo Contarini Del Bovolo. Its history-steeped features will captivate you. After the palace, continue your tour of the town with a visit to Grand Canal. Visitors usually appreciate the history-steeped features of this street.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Florence. There are so many fun and eye-opening activities to try out in Florence that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the town of Lido to find the best options for you!

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Make sure to reserve a table at Osteria Alla Staffa, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bistrot de Venise, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corte Sconta, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

Keep the evening going at Dolce Vita Venezia, a great choice for enjoying the after-dinner hours with a drink. You could also go to Tarnowska's American Bar, which offers a similarly pleasant setting and great drinks. Another option is Bar All'angolo, which provides an inviting environment for unwinding after a busy day out.

A leisurely self-drive holiday in Lido can’t get any better than this! Toast to another amazing day in Italy!

Day 9 introduces you to many popular attractions and activities in Venice, further proving that leisurely self-drive tours in Italy are extraordinary.

Next, go to Santa Maria Della Salute.

After visiting Punta Della Dogana - Pinault Collection and Santa Maria Della Salute, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to Peggy Guggenheim Collection. This history-steeped art gallery offers a unique experience. Gallerie Dell'accademia is another noteworthy attraction worthwhile a visit.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Venice offers a wide selection of experiences for every traveler.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Venice, explore the city like a local by trying out the best restaurants in the area.

Have a fantastic dining experience at Cantina Do Spade, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Al Gazzettino offers an enticing alternative with its varied menu. Additionally, Local is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

After dinner, it’s time to fall in love with the amazing nightlife in Venice and unwind at some of the best bars in the city.

Keep the excitement of the evening going by visiting a bar or two. Devils Forest Pub is an excellent place to start. You could also check out Bar Venetico, offering a different kind of charm. A last recommendation for the day is L'archivio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

Day 10 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Venice and drive in the direction of Milan for some laid-back sightseeing. You’ll end your day in Milan, where you’ll stay for 3 nights.

Rialto Bridge is must-visit historical landmark and a great option for a daytime tour of the area. Continue your journey to Ca' Pesaro International Gallery Of Modern Art, an often recommended art gallery, located just a leisurely stroll away. Next, head to Grassi Palace, a visually striking palace, also available for your discovery today.

After a day of exploration, relax at one of the top hotels or accommodations in Milan. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip in Italy.

Exploring the food culture in Milan offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Before calling it a day, visit one of the best bars in Milan. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Keep the evening going at Nottingham Forest, a great choice for enjoying the after-dinner hours with a drink. You could also go to Armani/bamboo Bar, which offers a similarly pleasant setting and great drinks. Another option is Mag Cafe, which provides an inviting environment for unwinding after a busy day out.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 2 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Milan, and meet locals along the way!

Visiting La Scala is always a good idea. This notable opera house is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Galleria Vittorio Emanuele Ii, a must-see shopping mall in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Duomo Di Milano Museum. This timeless church offers an enriching experience. For a change of pace, head to Cathedral Square, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Royal Palace Of Milan These sights offer a fulfilling end to a perfect day.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Milan.

Enjoy a delicious meal at Dessert Bar Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Following your dinner, dive into the local bar culture at Kilburn Cocktail Bar Milano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Frida, the perfect place for those looking to experience the best of the nightlife. Similarly, The Friends Pub Milano provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Soak in the unique atmosphere of Milan as you commemorate this day of your relaxed road trip with a toast. Cheers to a memorable, leisurely self-drive holiday in Italy!

Day 12 of your relaxed road trip through Italy means 24 hours of making the best memories in Milan. You’ll go sightseeing at famous attractions in Milan. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Milan!

Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Your adventure in Milan is only getting started when you visit Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a locally renowned local hot spot. Another notable attraction to explore is Santa Maria Delle Grazie Church. This interesting church is known for its visually striking appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Sforzesco Castle Art Library. This culturally significant castle offers a fascinating experience that many visitors find memorable. Parco Sempione is also worth visiting, along with Arch Of Peace. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Italy makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

Exploring new places makes you hungry. Luckily, Milan has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Enjoy a lovely dining experience at Bice Restaurant, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Alto Ristorante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Milan.

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

Free your mind of worries as you enjoy the taste of freedom on your laid-back road trip adventure across Italy.

On day 13 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

Let Pinacoteca Di Brera set the tone for the day. Spend some time admiring this visually striking art gallery before continuing your journey. Porta Garibaldi is your next stop. This often recommended monument is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Gae Aulenti. This mesmerizing public square is a sight to behold. To round off your sightseeing experience, visit Basilica Di Sant'ambrogio.

When you’re not exploring beautiful places, you can relax in Florence. Here, you can choose from the best hotels and other accommodations as you get to know more about the culture in the city.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Gosh*, a well-loved spot among locals and tourists. Or, head to Antico Caffè Del Moro - Art Bar Firenze. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Quelo Bar, another top-rated place in the area.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!