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

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Sit back and enjoy a relaxed 14-day road trip in Italy with this laid-back self-drive vacation.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Florence, Bologna, Venice, Lido, and Milan. Make yourself at home at top-rated hotels and stay 3 nights in Florence, 3 nights in Bologna, 4 nights in Venice, and 3 nights in Milan. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.

Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Florence, you’ll collect your rental car of choice. From there, you’ll begin your 14-day journey across Italy and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.

We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Piazza San Marco. Another highlight of this self-drive tour is the captivating Rialto Bridge.

Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Duomo Di Milano Museum. With this travel plan, you could also soak in the atmosphere of the memorable Ponte Vecchio. Get close to the spectacular Galleria Vittorio Emanuele Ii and the wonderful Piazzale Michelangelo. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.

Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 13 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 14 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 14-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed 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
Central Market
piazza della SignoriaUffizi GalleryPonte VecchioPalazzo PittiThe Boboli Gardens
Basilica of Santa Croce in FlorenceGalleria dell'AccademiaCathedral of Santa Maria del FioreBasilica of Santa Maria Novella
Palazzo Re EnzoFountain of Neptune, BolognaPiazza MaggioreBologna CathedralChurch of the Holy Savior
Two TowersPiazza Santo StefanoPorta Castiglionearco del MeloncelloDucati Museum
Basilica di San MartinoLa Piccola VeneziaPorta GallieraFaizan-e-Madina Bologna

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Day 1

Day 1

  • Florence - Arrival day
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  • Central Market
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Your relaxed road trip through Italy starts when you reach the incredible city of Florence, where you'll stay for 2 nights. You'll pick up your rental car in Florence and begin your adventure in Italy.

Florence 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 Central Market, 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise a toast as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Florence as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Florence
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Drive 4 km, 59 min

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

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!

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Piazza Della Signoria, an impressive public square in the city. Then, head to Uffizi Gallery 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 Ponte Vecchio. This is one of the city’s most wondrous history-steeped spots of interest. After exploring the historical landmark, visit the captivating Pitti Palace. Not far away, you'll also find The Boboli Gardens. This botanical garden is a romantic highlight in Florence.

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.

Experience shopping bliss at Florence as you explore Mercato Centrale. Take a leisurely stroll through unique and shops, where local treasures are waiting to be found. Beyond shopping, Mercato Centrale offers more options, including unique attractions, key services, and vibrant events.

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.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 3

Day 3

  • Florence
  • Bologna
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Drive 106 km, 2 hours 7 min

  • Basilica of Santa Croce in Florence
  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • Basilica of Santa Maria Novella
  • More

Day 3 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Bologna for 3 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Of Santa Croce In Florence. This culturally significant church is sure to ignite your curiosity. Next, dive into the photogenic features of Galleria Dell'accademia, a must-visit art gallery 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 Cathedral Of Santa Maria Del Fiore, an extraordinary church. For a change of scene, check out Basilica Di Santa Maria Novella, Firenze (fi), known for its symbolic features.

After a day of exploration, relax at one of the top hotels or accommodations in Bologna. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

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 Bologna, explore the city like a local by trying out the best restaurants in the area.

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, 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!

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Day 4

Day 4

  • Bologna
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Drive 1 km, 16 min

  • Palazzo Re Enzo
  • Fountain of Neptune, Bologna
  • Piazza Maggiore
  • Bologna Cathedral
  • Church of the Holy Savior
  • More

On day 4 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Palazzo Re Enzo is the perfect place to start. This palace is one of the most often recommended places to visit in Bologna. Next, head to Fountain Of Neptune, Bologna, an underrated monument, known for its respected 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 Piazza Maggiore. This visually striking public square is a highly recommended experience. Nearby, you'll also find Bologna Cathedral and Chiesa Del Santissimo Salvatore. 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 Bologna. There are so many fun and eye-opening activities to try out in Bologna 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!

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.

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.

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.

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

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

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Day 5

Day 5

  • Bologna
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Drive 17 km, 58 min

  • Two Towers
  • Piazza Santo Stefano
  • Porta Castiglione
  • arco del Meloncello
  • Ducati Museum
  • More

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

Today’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Two Towers. This popular monument is a picture-perfect place to see in Bologna. Continue your discovery at Piazza Santo Stefano, an enchanting public square with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Porta Castiglione. This often recommended monument offers a symbolic encounter with Bologna. Next, make your way to Arco Del Meloncello to add another highlight to your day. After that, visit Ducati Museum, a locally appreciated museum that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

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.

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.

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, stop at some of Bologna’s best bars to celebrate this day of your slow-paced adventure in Italy.

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

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

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Day 6

Day 6

  • Bologna
  • Venice
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Drive 156 km, 2 hours 13 min

  • Basilica di San Martino
  • La Piccola Venezia
  • Porta Galliera
  • Faizan-e-Madina Bologna
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Day 6 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Bologna and drive in the direction of the city of Venice for some laid-back sightseeing. You’ll end your day in the city of Venice, where you’ll stay for 4 nights.

Bologna is brimming with adventures. Today’s wonderful stops include a church, a street, a monument, a mosque and much more! Begin your sightseeing adventure at the often recommended San Martino and allow yourself time to explore. Just a short distance away you'll find your next stop, La Piccola Venezia, a romantic street that draws visitors from far and near.

Continue your journey to Porta Galliera, one of the city’s most often recommended spots that you shouldn’t miss. Another great site to visit is the intriguing Faizan-e-madina Bologna.

When you’re not exploring beautiful places, you’ll have a relaxed time at Venice. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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.

Experience a taste of local culinary excellence while in Venice by securing a table at Local. An esteemed 1-star Michelin restaurant, it features an exceptional contemporary menu. For an alternative taste experience, visit Wistèria, famous for its scrumptious contemporary and venetian dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Quadri, a local favorite celebrated for its exquisite modern cuisine in Venice. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for modern cuisine lovers seeking top-notch culinary experiences.

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.

Following your dinner, dive into the local bar culture at Al Parlamento. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to The Caffe Rosso, the perfect place for those looking to experience the best of the nightlife. Similarly, Adagio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 7

Day 7

  • Venice
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Drive 2 km, 32 min

  • Piazza San Marco
  • St Mark's Campanile
  • St Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • More

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!

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Venice. Begin your sightseeing with Piazza San Marco. This iconic public square is one of the top attractions in the city. Proceed to St Mark's Campanile, 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 St Mark's Basilica. This notable church is a traveler-favorite. Not far away, you’ll find Doge's Palace, another key site on your sightseeing itinerary. Bridge Of Sighs 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 exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

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.

Don’t miss out on dining at Generator Venice, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Nevodi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice 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.

After your meal, keep the night alive at a bar like Il Mercante, known for its lively atmosphere. The Irish Pub Venezia is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ai Stagneri offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 8

Day 8

  • Venice
  • More

Drive 7 km, 1 hour 39 min

  • Giardini della Biennale
  • Venetian Arsenal
  • Teatro La Fenice
  • Palazzo Contarini del Bovolo
  • Grand Canal
  • More

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Lido, where you'll stay for 2 nights, and see some of the town’s unforgettable attractions. To learn more of the town's culture, you'll also dine at the most popular restaurants in Lido, and meet locals along the way!

Get ready for an exciting day in Venice. Today’s sightseeing agenda includes a park, a historical landmark, an opera house, a palace, a street and much more! Begin your adventure at Giardini Della Biennale. This is a notable park you should not miss. Another must-see is Venetian Arsenal, an up-and-coming historical landmark in Venice.

When you’re ready for the next sight, head to Teatro La Fenice. From there, take a leisurely stroll to Palazzo Contarini Del Bovolo, another of the town’s well-known attractions. We recommend continuing your self-guided tour at Grand Canal, a romantic place of interest in the town.

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

Savor the flavors at Osteria Alla Staffa, a top pick for dinner tonight. Alternatively, Bistrot de Venise beckons with its unique menu offerings. Also, consider Corte Sconta. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

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.

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.

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

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Day 9

Day 9

  • Venice
  • More

Drive 4 km, 58 min

  • Punta della Dogana - Pinault Collection
  • Santa Maria della Salute
  • Peggy Guggenheim Collection
  • Gallerie dell'Accademia
  • More

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

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Venice on today’s itinerary. First up is the curiosity-inducing museum, Punta Della Dogana - Pinault Collection. Afterward, continue to Santa Maria Della Salute, a church 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 Peggy Guggenheim Collection. This notable art gallery is an essential stop. Following that, head to Gallerie Dell'accademia, another must-visit site that will enhance your experience.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Venice. There are so many fun and eye-opening activities to try out in Venice 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 Venice to find the best options for you!

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.

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.

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

To truly maximize your evening out, consider visiting Devils Forest Pub after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Venetico, another bar with an inviting ambiance. Similarly, L'archivio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 10

Day 10

  • Venice
  • Milan
  • More

Drive 271 km, 3 hours 43 min

  • Rialto Bridge
  • Ca' Pesaro International Gallery of Modern Art
  • Grassi Palace
  • More

Day 10 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Venice. By the end of the day, you’ll drive in the direction of the city of Milan, where you’ll stay at a top-rated hotel of your choice for 3 nights.

Start by visiting Rialto Bridge, a prime spot to begin your journey. This visually striking historical landmark is sure to impress. Next on your list is Ca' Pesaro International Gallery Of Modern Art, another must-visit landmark and up-and-coming art gallery renowned for its standout features.

While exploring and sightseeing, take time to savor the culture of Venice by sampling some local delicacies. When you’re ready for more sightseeing, head to Grassi Palace. This history-steeped palace is an essential place to visit for anyone looking for the full Venice experience.

In the city of Milan, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation 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.

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

Continue your lively evening at Nottingham Forest, a perfect place for winding down or revving up the night, depending on which mood you’re in. Armani/bamboo Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Mag Cafe ensures a night out tailored to your taste.

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

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Day 11

Day 11

  • Milan
  • More

Drive 1 km, 21 min

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Cathedral Square
  • Royal Palace of Milan
  • More

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!

Get ready for a day filled with fun adventures, romantic experiences, and picturesque spots in the charming city of Milan. Your adventure starts at La Scala, a well-known local hot spot. Another notable attraction to explore is Galleria Vittorio Emanuele Ii. This astonishing shopping mall is known for its romantic 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 Duomo Di Milano Museum. This enchanting church offers a fascinating experience that many visitors find memorable. Cathedral Square is also worth visiting, along with Royal Palace Of Milan. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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 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.

Make sure to reserve a table at Dessert Bar Milano, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Radisson Blu Hotel Milan, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Qui Si Mangia, a hidden gem nestled in Milan. 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, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Explore the vibrant nightlife at Kilburn Cocktail Bar Milano after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Frida for a great selection of flavorful drinks and a charming setting. Furthermore, The Friends Pub Milano is perfect for those looking to extend their night with a touch of local flavor.

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

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Day 12

Day 12

  • Milan
  • More

Drive 9 km, 1 hour

  • Leonardo da Vinci Museum of Science and Technology
  • Santa Maria delle Grazie Church
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • More

On day 12 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, 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 Milan, and meet locals along the way!

Today, you'll explore some of the most beautiful places in Milan, including a museum, a church, a castle, a park, a monument and much more! Start your day with a visit to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This well-known museum is a must-visit in the city. When you’re ready for your next discovery, continue to Santa Maria Delle Grazie Church, which may be one of the most inviting places you will experience today.

One of the best things about exploring Milan 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 Sforzesco Castle Art Library, an extraordinary castle in the city. If you’re up for more discoveries, don’t forget to reserve some time for Parco Sempione and Arch Of Peace.

Italy makes the perfect setting for a calming but fun exploration. 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.

Treat yourself to a delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

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

Continue your evening by exploring the vibrant nightlife scene at Bhangrabar, a prime destination for a thrilling night out. Also, don’t forget to check out Rufus Cocktail Bar, a bar that offers unique local touches. Likewise, Ostello Bello Grande provides an excellent alternative for a fun 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.

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Day 13

Day 13

  • Milan
  • Florence
  • More

Drive 320 km, 4 hours 30 min

  • Pinacoteca di Brera
  • Garibaldi Gate
  • Piazza Gae Aulenti
  • Basilica di Sant'Ambrogio
  • More

Day 13 of your relaxed road trip across the beautiful country of 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!

Prepare for a day full of family-friendly attractions, picturesque spots, and history-rich sites. When you’re ready, kick off your sightseeing adventure at Pinacoteca Di Brera. This captivating art gallery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Porta Garibaldi, one of the city’s best highlights.

Next, check out Piazza Gae Aulenti, one of the most locally renowned places to see in Milan. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Basilica Di Sant'ambrogio. Wander around and soak in the inviting atmosphere this church offers.

Continue your laid-back road trip exploration of the best attractions in Italy at Florence. Select from top hotels and accommodations in the city to recharge and rejuvenate.

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 Florence, 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 Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 14

Day 14

  • Florence - Departure day
  • More
  • piazzale Michelangelo
  • More

Day 14 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Florence.

Maximize your last day in Italy and go on a shopping spree in Florence’s shopping center, the lively San Lorenzo Market. Browse for souvenirs to remind you of your wonderful journey in Italy.

If you're up for some more sightseeing, begin at Piazzale Michelangelo. This famous observation deck is a popular place to see in the city.

Unwind and look back at the past 14 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Florence or just grab something light to keep you going.

If you're eager to try something different, consider Djària - American Bar, another top spot with a tantalizing menu.

Give yourself enough time to wave goodbye to Florence and begin your journey home. The unforgettable experiences you’ve collected along your 14-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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