Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, Bologna, and Milan
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Included
Description
Discover Italy stress-free with this 14-day relaxed road trip, winding through Pisa, Tirrenia, Florence, Bologna, Verona, Milan, and La Spezia. Enjoy a relaxing self-drive holiday through stunning landscapes and calm adventures.
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 Pisa, Tirrenia, Florence, Bologna, Verona, Milan, and La Spezia. Make yourself at home at top-rated hotels and stay 2 nights in Pisa, 2 nights in Florence, 4 nights in Bologna, and 5 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 Pisa, 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 Duomo Di Milano Museum. Another highlight of this self-drive tour is the captivating Verona Arena.
Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Ponte Vecchio. With this travel plan, you could also soak in the atmosphere of the memorable Leaning Tower Of Pisa. Get close to the spectacular Piazza Del Duomo, Pisa and the wonderful Galleria Vittorio Emanuele Ii. 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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Day 1
- Pisa - Arrival day
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- Knights' Square
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Your relaxed road trip through Italy starts when you reach the incredible city of Pisa, where you'll stay for 1 night. You'll pick up your rental car in Pisa and begin your adventure in Italy.
Pisa 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 Knights' Square, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.
Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Pisa. Make yourself at home and enjoy some downtime before heading out again.
As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.
Dine in style at Anima di Grano Pizzeria Napoletana Pisa Italy, a top recommendation for dinner tonight. Or, for a change of pace, il Mercante boasts a menu that's sure to impress. Also, be sure to check out La Ghiotteria. Known as a local hotspot, it’s a great choice for tonight in Pisa.
Before calling it a day, visit one of the best bars in Pisa. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Jeffer Cocktails & Friends stands out as an excellent choice for a post-dinner cocktail. Alternatively, Le Parisien Wine Bar offers an ideal atmosphere to enjoy the pleasures of the night. Las Volta Cocktailbar is also a great option that provides a perfect setting for a relaxing evening.
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 Pisa as you soak in the city’s unique vibe.
Day 2
- Pisa
- Florence
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Drive 132 km, 2 hours 22 min
- Leaning Tower of Pisa
- Piazza del Duomo, Pisa
- Pisa Cathedral
- Parco Regionale Migliarino, San Rossore, Massaciuccoli
- Bagno degli Americani
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On day 2 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.
Start your adventure at Leaning Tower Of Pisa. This timeless monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Piazza Del Duomo, Pisa, a must-see public square 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 Pisa Cathedral. This frequently visited church offers an enriching experience. For a change of pace, head to Parco Regionale Migliarino, San Rossore, Massaciuccoli, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Bagno Degli Americani. These sights offer a fulfilling end to a perfect day.
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.
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.
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.
If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.
Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across Italy.
Day 3
- Florence
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Drive 4 km, 1 hour 5 min
- piazzale Michelangelo
- Basilica of Santa Croce in Florence
- piazza della Signoria
- Uffizi Gallery
- Ponte Vecchio
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On day 3 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!
Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazzale Michelangelo. This romantic observation deck is a highlight of any visit in the city. Then, enjoy Basilica Of Santa Croce In Florence, another culturally significant attraction that never fails to captivate visitors. Next, head over to Piazza Della Signoria, one of the city’s most widely recognized attractions, known for its enchanting features.
If you’re looking for more, spend time soaking in the atmosphere of Uffizi Gallery. This romantic art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Ponte Vecchio, a wondrous historical landmark, and take a stroll around the area.
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!
Exploring the food culture in Florence 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 lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.
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.
Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.
Cherish every minute of your relaxed road trip vacation across Italy.
Day 4
- Florence
- Bologna
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Drive 105 km, 1 hour 54 min
- Cathedral of Santa Maria del Fiore
- Galleria dell'Accademia
- Central Market
- Basilica of Santa Maria Novella
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Day 4 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 Florence. By the end of the day, you’ll drive in the direction of the city of Bologna, where you’ll stay at a top-rated hotel of your choice for 4 nights.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Cathedral Of Santa Maria Del Fiore. This widely recognized church provides an insightful glimpse into the city's identity. Next, discover Galleria Dell'accademia, a detailed art gallery, promising a delightful encounter.
Continue your sightseeing with a visit to Central Market, a well-known food market. When you’re done, don’t forget to make a stop at the well-known Basilica Di Santa Maria Novella, Firenze (fi).
In the city of Bologna, 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 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.
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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.
A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Bologna.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing evening.
A leisurely self-drive holiday in Florence can’t get any better than this! Toast to another amazing day in Italy!
Day 5
- Bologna
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Drive 1 km, 26 min
- Palazzo Pallavicini
- Bologna Cathedral
- Piazza Maggiore
- Fountain of Neptune, Bologna
- Palazzo Re Enzo
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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 fun adventures, romantic experiences, and photo-friendly spots. The first attraction of today is Palazzo Pallavicini. This often recommended palace is a historic place to see in Bologna. Continue your discovery at Bologna Cathedral, a culturally significant church 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 Piazza Maggiore. This widely recognized public square offers an enchanting encounter with Bologna. Next, make your way to Fountain Of Neptune, Bologna to add another highlight to your day. After that, visit Palazzo Re Enzo, an up-and-coming palace 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.
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.
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.
Don’t miss out on dining 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.
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.
Continue the enjoyment post-dinner at Lime Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Macondo - Cocktail Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Onda Marina By Night. 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 6
- Bologna
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Drive 12 km, 1 hour 5 min
- arco del Meloncello
- Basilica of San Domenico
- Two Towers
- Piazza Santo Stefano
- Porta Santo Stefano
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Day 6 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!
Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Arco Del Meloncello. This historic monument is sure to ignite your curiosity. Next, dive into the heritage-rich features of Basilica Of San Domenico, a must-visit church 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 Two Towers, an interesting monument. For a change of scene, check out Piazza Santo Stefano, known for its visually striking features. We also recommend visiting Porta Santo Stefano. This monument is a must for anyone looking to experience the city to the fullest.
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 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 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.
After dinner, it’s time to fall in love with the amazing nightlife in Bologna and unwind at some of the best bars in the city.
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.
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.
Day 7
- Bologna
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Drive 19 km, 1 hour 11 min
- Ducati Museum
- Porta Galliera
- Botanical Garden and Herbarium
- Pinacoteca Nazionale di Bologna
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On day 7 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!
Savor the day by visiting some of the best places to see in Bologna, including a museum, a monument, a botanical garden, an art gallery and much more! Start your adventure at Ducati Museum. This worthwhile museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta Galliera located in Bologna for another exciting encounter.
Next, immerse yourself in the setting of Botanical Garden And Herbarium. Its romantic features will captivate you. After the botanical garden, continue your tour of the city with a visit to Pinacoteca Nazionale Di Bologna. Visitors usually appreciate the visually striking features of this art gallery.
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.
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.
Savor the flavors at Pappare' - Bologna, a top pick for dinner tonight. Alternatively, Mister Coffee Bistrò beckons with its unique menu offerings. Also, consider All'Osteria Bottega. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.
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.
Let the evening flow smoothly from dinner to drinks at Bar Piratello, a top-rated bar in the area. For other recommendations, Bar Carlo provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Maurizio offers a memorable night with diverse drink options and excellent service.
Soak in the unique atmosphere of Bologna as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday in Italy!
Day 8
- Bologna
- Milan
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Drive 301 km, 4 hours 12 min
- Castelvecchio Museum
- Castelvecchio Bridge
- Verona Arena
- piazza delle Erbe
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Day 8 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Verona and drive in the direction of the city of Milan for some laid-back sightseeing. You’ll end your day in the city of Milan, where you’ll stay for 5 nights.
Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Castelvecchio Museum is the first of them. Spend some time admiring this stunning museum before continuing your journey. Castelvecchio Bridge is your next stop. This well-known monument is one of the best-rated sights in Bologna.
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 Verona Arena. This visually striking stadium is a sight to behold. To round off your sightseeing experience, visit Piazza Delle Erbe.
After a day of exploration, relax at one of the top hotels or accommodations in Milan. 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 Milan, explore the city like a local by trying out the best restaurants in the area.
Dive into a culinary adventure like no other in Milan by booking a table at Enrico Bartolini al Mudec. This popular restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another culinary dining option, venture to Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Il Luogo Aimo e Nadia, a top local restaurant known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.
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 to celebrate another day of your laid-back and relaxed road trip experience in Italy!
Day 9
- Milan
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Drive 1 km, 21 min
- La Scala
- Galleria Vittorio Emanuele II
- Duomo di Milano
- Cathedral Square
- Royal Palace of Milan
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Day 9 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Milan allows for both. Start by heading to La Scala. This well-known opera house provides an insightful glimpse into the city's identity. Next, discover Galleria Vittorio Emanuele Ii, a romantic shopping mall, promising a delightful encounter.
Continue your sightseeing with a visit to Duomo Di Milano Museum, a world-famous church. When you’re done, don’t forget to make a stop at the curiosity-inducing Cathedral Square. Round off your day at Royal Palace Of Milan, another gem in Milan with visually striking features to discover.
Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Milan. There are so many fun and eye-opening activities to try out in Milan 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!
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.
Treat yourself to a delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.
If you feel like it, head out to a bar to celebrate another fantastic day in Milan 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 Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.
Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!
Day 10
- Milan
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Drive 6 km, 48 min
- Arch of Peace
- Triennale di Milano
- Sempione Park
- Castello Sforzesco
- Piazza Castello Fountain
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Day 10 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!
Today’s agenda in Milan includes a monument, a museum, a park, a castle, a public square and much more! Arch Of Peace is must-visit monument and a great starting point for the day. Next, continue your journey to Triennale Di Milano, an underrated museum, located just a leisurely stroll away. Next, head to Parco Sempione, a romantic park, 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 famous Sforzesco Castle Art Library. If you’re looking for more, Piazza Castello Fountain is also a curiosity-inducing attraction that is worthwhile a visit.
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.
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 Bice Restaurant, 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 Alto Ristorante, 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 Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
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 Bhangrabar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Rufus Cocktail Bar, which offers a similarly pleasant setting and great drinks. Another option is Ostello Bello Grande, which provides an inviting environment for unwinding after a busy day out.
A leisurely self-drive holiday in Milan can’t get any better than this! Toast to another amazing day in Italy!
Day 11
- Milan
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Drive 8 km, 1 hour 6 min
- Piazza Gae Aulenti
- Pinacoteca di Brera
- Milan Natural History Museum
- Villa Necchi Campiglio
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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!
Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most notable attractions included on the itinerary is Piazza Gae Aulenti. This gorgeous public square will help you start your sightseeing on top. Then, take a leisurely stroll to Pinacoteca Di Brera and learn what makes this eye-catching art gallery unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the curiosity-inducing Milan Natural History Museum. After exploring the museum, head to Villa Necchi Campiglio. This frequently visited museum is a highlight in Milan.
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 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.
Enjoy a delicious meal at Ristorante la Brisa, a highly-rated dining destination in Milan. If you're eager to try something different, consider Pasticceria San Carlo, another top spot with a tantalizing menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.
Hang out and unwind at some of the top bars in Milan.
To truly maximize your evening out, consider visiting Qc Termemilano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yguana Cafè, another bar with an inviting ambiance.
Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!
Day 12
- Milan
- More
Drive 9 km, 59 min
- Basilica di Sant'Ambrogio
- Leonardo da Vinci Museum of Science and Technology
- Santa Maria delle Grazie Church
- MUDEC - Museum of Cultures
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Day 12 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.
Today’s itinerary in Milan covers several incredible sights, including a church and a museum. Start your adventure at Basilica Di Sant'ambrogio. This locally renowned church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a must-see museum 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 Santa Maria Delle Grazie Church. This well-known church offers an enriching experience. For a change of pace, head to Mudec - Museum Of Cultures, where you can take in photogenic features. These sights offer a fulfilling end to a perfect day.
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.
Treat yourself to a wonderful meal at Vento di Sardegna, a top-rated dining spot in Milan. If you're in the mood for something new, try Palazzo Parigi Hotel & Grand Spa Milano, another premier location with a delectable menu. You might also want to book a table at Galleria Restaurant. 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.
Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!
Day 13
- Milan
- Pisa
- More
Drive 312 km, 4 hours 5 min
- Castello San Giorgio
- Giardini Pubblici
- Technical Naval Museum of Spezia
- More
Day 13 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Pisa for 1 night. 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.
Discover a day packed with fun adventures, breathtaking views, and picturesque spots in Milan. Begin your sightseeing with Castello San Giorgio. This worthwhile castle is one of the top attractions in the city. Proceed to Giardini Pubblici, another must-visit attraction.
As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Technical Naval Museum Of Spezia. This beloved museum is a traveler-favorite.
When you’re not exploring beautiful places, you’ll have a relaxed time at Pisa. 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 the food culture in Pisa 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.
Treat yourself to a delightful dinner at Ristorante Capodimonte Pisa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Locanda Dei Pisani Doc Pisa? It's another excellent option with a diverse menu. Consider reserving a table at Baribaldi Pisa as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.
Experience the amazing nightlife in Pisa and unwind at the coolest bars in the city.
After your meal, keep the night alive at a bar like Bar Mocambo, known for its lively atmosphere. Tree is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Chupiteria offers an excellent atmosphere for those looking to amp up the evening.
Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!
Day 14
- Pisa - Departure day
- More
- Logge dei Banchi
- 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 Pisa.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Pisa's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.
If you're up for some more sightseeing, begin at Logge Dei Banchi. This up-and-coming public square 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 Pisa or just grab something light to keep you going.
Savor the flavors at Restaurant -Pizzeria Il Mio Capriccio, a top pick for dinner tonight. Alternatively, Ristorante alle Bandierine beckons with its unique menu offerings.
Give yourself enough time to wave goodbye to Pisa 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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