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

Day 2 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. 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 Florence!

Whatever your travel style is, Piazza Della Signoria is an essential stop in Florence. This extraordinary public square provides an insightful glimpse into the city's identity. Next, discover Uffizi Gallery, a picture-perfect art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Ponte Vecchio, a timeless historical landmark. When you’re done, don’t forget to make a stop at the interesting Pitti Palace. Round off your day at The Boboli Gardens, another gem in Florence with history-steeped features to discover.

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.

Bring home unique finds from Florence's bustling shopping hub, Via de' Tornabuoni. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via de' Tornabuoni offers plenty of options, including primary services, unique landmarks, and community events.

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.

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean 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 Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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

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.

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

Day 3 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Bologna for 3 nights.

Basilica Of Santa Croce In Florence is an ideal stop early in the day. This locally renowned church is a must-visit in the city. When you’re ready for your next discovery, continue to Galleria Dell'accademia, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Cathedral Of Santa Maria Del Fiore, an astonishing church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Di Santa Maria Novella, Firenze (fi).

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

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.

Set out on a gastronomic journey in Bologna by reserving a table at Ahimè. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of country cooking cuisine. For a different taste, head over to I Portici, renowned for its delectable creative and contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Bologna. The bars in Bologna make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Day 4 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Palazzo Re Enzo brings Bologna's character to life. This breathtaking palace is a highlight of any visit in the city. Then, enjoy Fountain Of Neptune, Bologna, another noteworthy attraction that never fails to captivate visitors. Next, head over to Piazza Maggiore, one of the city’s most famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Bologna Cathedral. This majestic church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Chiesa Del Santissimo Salvatore, a worthwhile church, and take a stroll around the area.

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 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 fantastic dining experience at Bononia Cafè, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Via Con Me offers an enticing alternative with its varied menu. Additionally, Trattoria Pizzeria La Mela is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

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.

After enjoying a fulfilling meal, continue your evening at Lime Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Macondo - Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Onda Marina By Night provides an excellent environment for a relaxed and enjoyable evening.

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 5 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Bologna is brimming with adventures.

Two Towers leaves a lasting impression. This monument is one of the most captivating places to visit in Bologna. Next, head to Piazza Santo Stefano, a frequently visited public square, known for its enchanting features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Porta Castiglione. This symbolic monument is a highly recommended experience. Nearby, you'll also find Arco Del Meloncello and Ducati Museum Visit these for an interesting touch to your journey.

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 Bologna 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 Bologna.

Enjoy a lovely dining experience at Va Mo Là, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia. It’s yet another ideal choice to enhance your time in Bologna tonight.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Bologna. The bars in Bologna make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Aurum stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Senza Nome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Ristretto is also a great option that provides a perfect setting for a relaxing evening.

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

Day 6 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Bologna and drive in the direction of Venice for some laid-back sightseeing. You’ll end your day in Venice, where you’ll stay for 4 nights.

Visiting San Martino is always a good idea. This curiosity-inducing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of La Piccola Venezia, a must-see street 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 Porta Galliera. This intriguing monument offers an enriching experience. For a change of pace, head to Faizan-e-madina Bologna, where you can take in stunning features.

In Venice, 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.

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.

Get ready for an unforgettable culinary journey in Venice by reserving a table at Local. Renowned as a 1-star Michelin restaurant, it offers an exceptional contemporary menu. For a different taste experience, head to Wistèria, recognized for its delicious contemporary and venetian dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Quadri, a local favorite known for its delightful modern cuisine in Venice. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for modern foodies seeking culinary excellence.

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.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Caffe Rosso, a bar catering to every mood and preference. Adagio likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 7 of your relaxed road trip through Italy means 24 hours of making the best memories in Venice. You’ll go sightseeing at famous attractions in Venice. 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 Venice!

Enjoy all that Piazza San Marco has to offer. This is a wondrous public square you should not miss. Another must-see is St Mark's Campanile, a beloved monument in Venice.

When you’re ready for the next sight, head to St Mark's Basilica. From there, take a leisurely stroll to Doge's Palace, another of the city’s interesting attractions. We recommend continuing your self-guided tour at Bridge Of Sighs, a symbolic place of interest in the city.

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.

Enjoy a delicious meal at Generator Venice, a highly-rated dining destination in Venice. If you're eager to try something different, consider Nevodi, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

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.

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

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

Day 8 introduces you to many popular attractions and activities in Lido, further proving that leisurely self-drive tours in Italy are extraordinary.

No visit to Venice is complete without Giardini Della Biennale. This locally renowned park is one of the top attractions in the town. Proceed to Venetian Arsenal, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Teatro La Fenice. This captivating opera house is a traveler-favorite. Not far away, you’ll find Palazzo Contarini Del Bovolo, another key site on your sightseeing itinerary. Grand Canal is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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, Venice has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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.

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

If you’re not ready to end the night just yet, Dolce Vita Venezia offers a perfect venue to relax and savor a drink. Similarly, Tarnowska's American Bar is well-suited for those looking to unwind in a social setting. Bar All'angolo is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 9 of your leisurely self-drive tour across Italy, you’ll go deep into Venice, 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 Venice, and meet locals along the way!

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 enchanting art gallery offers a unique experience. Gallerie Dell'accademia is another noteworthy attraction worthwhile a visit.

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 Venice 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.

Enjoy a delicious meal at Cantina Do Spade, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Trattoria Al Gazzettino, another top spot with a mouthwatering menu. You might also want to secure a reservation at Local. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

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

Let the evening flow smoothly from dinner to drinks at Devils Forest Pub, a top-rated bar in the area. For other recommendations, Bar Venetico provides a perfect setting for rounding out your night with style and great drinks. Likewise, L'archivio offers a memorable night with diverse drink options and excellent service.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

Day 10 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Venice. By evening, drive toward the Milan, where you’ll stay at a top-rated hotel of your choice for 3 nights.

Check out the timeless historical landmark, Rialto Bridge. Afterward, continue to Ca' Pesaro International Gallery Of Modern Art, an art gallery every traveler should visit. As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Grassi Palace. This intriguing palace is an essential stop.

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

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 Milan, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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

Cap off your dinner by heading to Nottingham Forest, ideal for a leisurely evening with a drink in hand. Armani/bamboo Bar is another bar that offers an enjoyable setting. Similarly, Mag Cafe 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 11 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!

To truly experience Milan, make sure to drop by La Scala. This notable opera house is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Galleria Vittorio Emanuele Ii, one of the city’s best highlights.

Next, check out Duomo Di Milano Museum, one of the most timeless places to see in Milan. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Cathedral Square. Wander around and soak in the romantic atmosphere this public square offers. Then, head to Royal Palace Of Milan, a top-rated palace that adds another dimension to your day.

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 Milan 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.

Treat yourself to a wonderful meal at Dessert Bar Milano, a top-rated dining spot in Milan. If you're in the mood for something new, try Radisson Blu Hotel Milan, another premier location with a delectable menu. You might also want to book a table at Ristorante Qui Si Mangia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

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

After savoring a delicious meal, step into the vibrant nightlife at Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 12 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.

Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is must-visit museum and a great option for a daytime tour of the area. Continue your journey to Santa Maria Delle Grazie Church, a notable church, located just a leisurely stroll away. Next, head to Sforzesco Castle Art Library, a breathtaking castle, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. When you're ready, let your sightseeing route take you to the impressive Parco Sempione. If you’re looking for more, Arch Of Peace is also a locally renowned attraction that is worthwhile a visit.

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

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 Milan, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Dine in style at Bice Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Alto Ristorante boasts a menu that's sure to impress. Also, be sure to check out Nero 9. Known as a local hotspot, it’s a great choice for tonight in Milan.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bhangrabar, a well-loved spot among locals and tourists. Or, head to Rufus Cocktail Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ostello Bello Grande, another top-rated place in the area.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in 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.

Start your day at Pinacoteca Di Brera. This photogenic art gallery is a well-known place to see in Milan. Then, wander over to Porta Garibaldi. If eye-catching sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Gae Aulenti. This visually striking public square is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Basilica Di Sant'ambrogio is a popular spot in the city that will captivate you with its unique charm.

You'll be staying in Florence on this laid-back road trip through Italy. You'll stay here for 1 night.

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.

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly 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.

Hang out and unwind at some of the top bars in Florence.

Continue your lively evening at Gosh*, a perfect place for winding down or revving up the night, depending on which mood you’re in. Antico Caffè Del Moro - Art Bar Firenze is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Quelo Bar ensures a night out tailored to your taste.

Toast to another unforgettable and relaxing road trip adventure in Italy!