12-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Como, Verona, Venice, Florence, San Gimignano, and Rome
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Experience the freedom of the open road in Italy as you embark on an unforgettable 12-day road trip! This experience caters to every traveler, featuring destinations like Milan, Ossuccio, Lenno, Colonno, Como, Verona, Venice, Florence, Pisa, Siena, San Gimignano, and Rome.
This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Milan, 1 night in Como, 1 night in Verona, 2 nights in Venice, 2 nights in Florence, 1 night in San Gimignano, and 1 night in Rome. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!
With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.
Upon arriving in Milan, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.
An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Pantheon are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Navona, learn more about the unique Piazza San Marco, and immerse yourself in the vibrant atmosphere of Rialto Bridge.
As you hit the open road and drive through Milan, Ossuccio, Lenno, Colonno, Como, Verona, Venice, Florence, Pisa, Siena, San Gimignano, and Rome, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.
Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.
This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.
The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!
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Day 1
- Milan - Arrival day
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- La Scala
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Welcome to Milan, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 2 nights immersing yourself in Milan's charm before embarking on the next leg of your journey.
Milan 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 La Scala, 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 Milan. 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 Milan, it's often a good idea to reserve a table in advance.
Don’t miss out on dining at Hotel Morfeo Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Contraste, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Galles Milano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.
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 a toast to the start of your 12-day road trip in Italy!
Day 2
- Milan
- More
Drive 7 km, 57 min
- Arch of Peace
- Sempione Park
- Castello Sforzesco
- Pinacoteca di Brera
- Palazzo della Ragione
- Navigli
- More
Day 2 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in Milan by discovering the best things there are to see and do in the city.
Make sure to visit Navigli, a popular neighborhood in Milan. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.
Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a monument, a park, a castle, an art gallery, a palace and much more! Begin your adventure at Arch Of Peace. This is a popular monument you should not miss. Another must-see is Parco Sempione, an impressive park in Milan.
When you’re ready for the next sight, head to Sforzesco Castle Art Library. From there, take a leisurely stroll to Pinacoteca Di Brera, another of the city’s locally renowned attractions. We recommend continuing your self-guided tour at Palazzo Della Ragione, a heritage-rich place of interest in the city.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
Experience shopping bliss at Milan as you explore Via della Moscova. Take a leisurely stroll through unique boutiques and shops, where local treasures are waiting to be found. Beyond shopping, Via della Moscova offers more options, including cafes, unique attractions, key services, and vibrant events.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Dine in style at Dessert Bar Milano, a top recommendation for dinner tonight. Or, for a change of pace, Radisson Blu Hotel Milan boasts a menu that's sure to impress. Also, be sure to check out Ristorante Qui Si Mangia. Known as a local hotspot, it’s a great choice for tonight in Milan.
After your meal, keep the night alive at a bar like Kilburn Cocktail Bar Milano, known for its lively atmosphere. Bar Frida is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, The Friends Pub Milano offers an excellent atmosphere for those looking to amp up the evening.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 3
- Milan
- Como
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Drive 117 km, 2 hours 45 min
- Sacro Monte della Beata Vergine del Soccorso - Ossuccio (co)
- Villa del Balbianello
- Botanical Garden of Villa Carlotta
- Greenway del Lago di Como
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Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 4 vibrant destinations - Ossuccio, Lenno, Rogaro, and Colonno. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Como. You will spend 1 night here for some well-deserved relaxation.
Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the frequently visited Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co), an enchanting church in Milan. Next, go to Villa Del Balbianello.
After visiting Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co) and Villa Del Balbianello, have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to Botanical Garden Of Villa Carlotta. This eye-catching botanical garden offers a unique experience. Greenway Del Lago Di Como is another noteworthy attraction worthwhile a visit.
When you’re done exploring for the day, you’ll drive to your hotel in Como. Check in and spend some time relaxing before you head out to tour the city.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Como. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Enjoy a lovely meal at La Vita è Bella Ristorante - Insalateria, a top-rated place to have dinner tonight.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Fresco Cocktail Shop stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Il Cortiletto offers an ideal atmosphere to enjoy the pleasures of the night. Bar Pinocchio is also a great option that provides a perfect setting for a relaxing evening.
Savor another day of unforgettable experiences in Italy!
Day 4
- Como
- Verona
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Drive 203 km, 2 hours 42 min
- Castelvecchio Museum
- Porta Borsari
- piazza delle Erbe
- Verona Arena
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Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Verona. At the end of the day, you will enjoy the comforts of a top-rated hotel in Verona, which will be your home away from home for 1 night.
Brace yourself for today’s incredible lineup of attractions in Como, featuring family-friendly attractions, scenic views, and picturesque spots. Start at Castelvecchio Museum, a locally renowned museum in the city. Then, head to Porta Borsari and soak in the ambiance of this heritage-rich historical landmark.
There are many interesting places to see in Como, and when you are ready for more, go to Piazza Delle Erbe. This is one of the city’s most notable history-steeped spots of interest. After exploring the public square, visit the timeless Verona Arena.
At the end of the day, you will drive to Verona, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Verona. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Make sure to reserve a table at La Griglia, an iconic dining spot in Verona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Vecio Macello, a popular restaurant in Verona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Via Fama Cafè | Verona, a hidden gem nestled in Verona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Round off your dining experience by visiting Archivio, a prime location for a drink. Alternatively, explore the distinctive characteristics of La Segreteria Café, a bar catering to every mood and preference. Grande Giove Cocktail Bar likewise offers a unique atmosphere, perfect for a memorable night out.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 5
- Verona
- Venice
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Drive 126 km, 2 hours 8 min
- Bridge of Sighs
- Doge's Palace
- St Mark's Basilica
- Piazza San Marco
- Rialto Bridge
- Grand Canal
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Dive into day 5 of your remarkable road trip in Italy. Today you will explore Venice, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Venice. You’ll stay here for 2 nights.
Today's adventure in Verona promises more breathtaking discoveries and enriching experiences! Begin at Bridge Of Sighs. This history-steeped monument is a highlight of any visit in the city. Then, enjoy Doge's Palace, another UNESCO world heritage-listed attraction that never fails to captivate visitors. Next, head over to St Mark's Basilica, one of the city’s most notable attractions, known for its history-steeped features.
If you’re looking for more, spend time soaking in the atmosphere of Piazza San Marco. This grand public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Rialto Bridge, a wondrous historical landmark, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Grand Canal before you head back to your hotel.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Venice. Venice offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
Indulge in a memorable dining experience at one of Venice's most popular restaurants, and connect with friendly locals for an authentic adventure.
Make sure to reserve a table at Bauer Hotel, 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 L'Osteria Le Guglie, 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 Corner Pub, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Let the evening flow smoothly from dinner to drinks at Al Parlamento, a top-rated bar in the area. For other recommendations, The Caffe Rosso provides a perfect setting for rounding out your night with style and great drinks. Likewise, Adagio offers a memorable night with diverse drink options and excellent service.
Get a good night's sleep and look forward to another great day on the road in Italy!
Day 6
- Venice
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Drive 4 km, 37 min
- Punta della Dogana - Pinault Collection
- Santa Maria della Salute
- Peggy Guggenheim Collection
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On day 6 of your road trip, you will have an entire day to explore Venice. You’ll stay in Venice for 1 night and discover all the best things to see and do in the area.
Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Venice on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Punta Della Dogana - Pinault Collection is the first of them. Santa Maria Della Salute is your next stop. This often recommended church is one of the best-rated sights in Venice.
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 Peggy Guggenheim Collection. This enchanting art gallery is a sight to behold.
Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.
After a day of adventure, treat yourself to an exquisite dinner at one of Venice's best restaurants.
Make sure to reserve a table at Generator Venice, 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 Nevodi, 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 Ristorante La Piazza, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
After your delicious meal, get a taste of the vibrant nightlife with a visit to Il Mercante, known for its inviting atmosphere. The Irish Pub Venezia is another great option if you’re looking for a place to get the night started. Similarly, Ai Stagneri provides a great setting to enjoy the night away.
Get a good night's sleep and look forward to another great day on the road in Italy!
Day 7
- Venice
- Florence
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Drive 259 km, 3 hours 26 min
- Piazza della Repubblica
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Croce in Florence
- Uffizi Gallery
- Ponte Vecchio
- piazza della Signoria
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On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.
Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Venice on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Della Repubblica is the first of them. Spend some time admiring this romantic public square before continuing your journey. Cathedral Of Santa Maria Del Fiore is your next stop. This astonishing church is one of the best-rated sights in Venice.
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 Basilica Of Santa Croce In Florence. This heritage-rich church is a sight to behold. To round off your sightseeing experience, visit Uffizi Gallery and Ponte Vecchio. If time allows, end your day with Piazza Della Signoria, a history-steeped public square that offers a memorable conclusion to your exploration.
When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.
As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.
Don’t miss out on dining at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.
After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.
Celebrate another amazing day of your road trip adventure in Italy!
Day 8
- Florence
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Drive 197 km, 2 hours 52 min
- Leaning Tower of Pisa
- Angelo Caduto
- Pisa Cathedral
- Campo santo
- Piazza del Duomo, Pisa
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Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa.
Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the iconic Leaning Tower Of Pisa, a detailed monument in Florence. Next, go to Angelo Caduto.
After visiting Leaning Tower Of Pisa and Angelo Caduto, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Pisa Cathedral. This breathtaking church offers a unique experience. Campo Santo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Del Duomo, Pisa, one of the most grand places to visit in Florence.
When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.
After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.
Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.
Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 9
- Florence
- San Gimignano
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Drive 118 km, 2 hours 22 min
- Fortezza Medicea
- piazza del Campo
- Pubblico Palace
- Siena Cathedral
- Parco della Rocca
- Rocca di Montestaffoli
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On day 9 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Siena and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most often recommended attractions included on the itinerary is Fortezza Medicea (siena). This historic monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Campo and learn what makes this visually striking public square unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the frequently visited Pubblico Palace. After exploring the palace, head to Siena Cathedral. This captivating church is a highlight in Florence. As your day continues, stop by Parco Della Rocca, known for its awe-inspiring features. Lastly, don’t forget to check out the frequently visited Rocca Di Montestaffoli. Enjoy exploring this incredible castle at your own pace.
At the end of the day, you will drive to San Gimignano, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.
After a day of adventure, treat yourself to an exquisite dinner at one of San Gimignano's best restaurants.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 10
- San Gimignano
- Rome
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Drive 281 km, 4 hours 9 min
- Castel Sant'Angelo
- Piazza Navona
- Pantheon
- Trevi Fountain
- Piazza di Spagna
- Basilica di Santa Maria Maggiore
- More
Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 1 night here for some well-deserved relaxation.
Today’s agenda in San Gimignano includes a castle, a public square, a monument, a church and much more! Castel Sant'angelo is must-visit castle and a great starting point for the day. Next, continue your journey to Piazza Navona, a wondrous public square, located just a leisurely stroll away. Next, head to Pantheon, a heritage-rich monument, also available for your discovery today.
Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for San Gimignano. When you're ready, let your sightseeing route take you to the globally renowned Trevi Fountain. If you’re looking for more, Piazza Di Spagna is also a timeless attraction that is worthwhile a visit. Lastly, don’t miss Basilica Di Santa Maria Maggiore, a place of photogenic interest in the city.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.
Enjoy a delicious meal at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.
After your delicious meal, get a taste of the vibrant nightlife with a visit to La Botticella Of Poggi Giovanni, known for its inviting atmosphere. Almalu Trastevere is another great option if you’re looking for a place to get the night started. Similarly, Bar Viminale Di Pepi Maurilio provides a great setting to enjoy the night away.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 11
- Rome
- Milan
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Drive 581 km, 6 hours 18 min
- St Peter's Basilica
- piazza del Popolo
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Embark on another extraordinary experience on day 11 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Vatican City and Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.
Start your day with a visit to St. Peter's Basilica. This globally renowned major basilica is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Popolo, which may be one of the most detailed places you will experience today.
When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and spend some time relaxing before you head out to tour the city.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Savor the flavors at Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.
Explore the vibrant nightlife at Bhangrabar after your meal, a hub for lively evenings and memorable moments. Or, head to Rufus Cocktail Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Ostello Bello Grande is perfect for those looking to extend their night with a touch of local flavor.
Say good night to Milan and look forward to another great day of your road trip in Italy!
Day 12
- Milan - Departure day
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- Duomo di Milano
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Day 12 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Milan before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.
If you're up for some more sightseeing, begin at Duomo Di Milano Museum. This timeless church is a popular place to see in the city.
Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones. For those seeking luxury items, check out the area’s high-end stores.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Milan.
You’ll then say farewell to Milan. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!
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