Two-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Como, Verona, Venice, Florence, Siena, and Monterosso al Mare

Day 2 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

One of the most iconic places you can visit today in Milan is Via Monte Napoleone. Allow yourself some time to explore this street and discover its unique quirks. You'll also find many of the best sightseeing spots nearby. You can also explore Brera, a neighborhood that offers a glimpse into local life and culture.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and historic treasures. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Santa Maria Delle Grazie Church is the first of them. Spend some time admiring this UNESCO world heritage-listed church before continuing your journey. La Scala is your next stop. This interesting opera house is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Galleria Vittorio Emanuele Ii. This enchanting shopping mall is a sight to behold. To round off your sightseeing experience, visit Duomo Di Milano Museum.

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 Milan's best restaurants.

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

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.

Raise your glass to another unforgettable day in Italy!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, San Maurizio, Tavernola, and Como. When you’re not sightseeing, take time to relax at your selected hotel in Como, where you’ll be staying for 2 nights.

Bring your curiosity for today’s adventure around Milan. Some of the hamlet’s most loved attractions await! Faro Voltiano Di Brunate is the perfect place to start. This monument is one of the most up-and-coming places to visit in Milan. Next, head to Villa Olmo, an often recommended palace, known for its visually striking 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 Tempio Voltiano. This breathtaking museum is a highly recommended experience. Nearby, you'll also find Saint Mary Assunta Cathedral. Visit these for an interesting touch to your journey.

At the end of the day, you will drive to Como, 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 Como's best restaurants.

Have a fantastic dining experience at L’Antica Trattoria, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Gesumin Restaurant offers an enticing alternative with its varied menu. Additionally, Pronobis is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Como.

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

Head back to your accommodation in Como and get some rest in preparation for another magical day of your road trip in Italy!

On day 4 of your road trip, you’ll start and end your day in Como, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Loppia, Bellagio, Rogaro, and Ossuccio. You still have 1 night left in Como.

Get ready to discover some of the most iconic wonders in Como, including a botanical garden, a boardwalk, a canyon, a museum, a church and much more! Start your day at I Giardini Di Villa Melzi. This standout botanical garden is a worthwhile place to see in Como. Then, wander over to Lungolago Europa. If romantic sites excite you, this boardwalk will be right up your alley. Nearby, you’ll also find Orrido Di Bellano. This mesmerizing canyon is a favorite among visitors.

Como offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Villa Carlotta (lake Como) is an often recommended spot in the hamlet that will captivate you with its unique charm. When you’re done at the museum, don’t forget to check out the enchanting Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co). Take a moment to appreciate the fascinating details of this intriguing church.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Como.

After a day of adventure, treat yourself to an exquisite dinner at one of Como's best restaurants.

Make sure to reserve a table at Alle Terrazze Como, an iconic dining spot in Como. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Vita è Bella Ristorante - Insalateria, a popular restaurant in Como. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sant'Anna, a hidden gem nestled in Como. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your meal, keep the night alive at a bar like Minimalismo Livingroom Wine & Cocktail Bar, known for its lively atmosphere. Como Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Hemingway offers an excellent atmosphere for those looking to amp up the evening.

Take some time to reflect on your day and savor another beautiful night in Italy.

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Verona, 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 Verona. You’ll stay here for 2 nights.

Savor the day by visiting some of the best places to see in Como, including a castle, a historical landmark, a public square, a museum, a monument, a stadium and much more! Start your adventure at Castel San Pietro. This up-and-coming castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Ponte Pietra located in Como for another exciting encounter.

Next, immerse yourself in the setting of Piazza Delle Erbe. Its instagrammable features will captivate you. After the public square, continue your tour of the city with a visit to Castelvecchio Museum. Visitors usually appreciate the eye-catching features of this museum. Next up is Castelvecchio Bridge, a highly recommended monument. For a change of pace, head to Verona Arena. As one of the most timeless attractions in Como, this stadium is the perfect place to end your self-guided sightseeing tour.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Verona. Verona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Verona. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Savor the flavors at La Griglia, a top pick for dinner tonight. Alternatively, Vecio Macello beckons with its unique menu offerings. Also, consider Via Fama Cafè | Verona. With its consistent customer satisfaction, it’s an excellent option for dining in Verona tonight.

If you’re not ready to end the night just yet, Archivio offers a perfect venue to relax and savor a drink. Similarly, La Segreteria Café is well-suited for those looking to unwind in a social setting. Grande Giove Cocktail Bar is another excellent spot to enjoy a nightcap after a delightful meal.

Celebrate another amazing day of your road trip adventure in Italy!

Wake up to day 6 of your extraordinary road trip in Italy. With 1 night left in Verona, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Get ready for an exciting day in Verona. Today’s sightseeing agenda includes an archeological site, a castle, and a beach. Begin your adventure at Archaeological Site Of Grotte Di Catullo. This is a well-known archeological site you should not miss. Another must-see is Scaliger Castle, a widely recognized castle in Verona.

When you’re ready for the next sight, head to Beach Brema Sirmione. From there, take a leisurely stroll to Castle Of Malcesine, another of the town’s interesting attractions.

When you’re done exploring for the day, you’ll return to Verona and your accommodation.

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.

Enjoy a delicious meal at Trattoria I Masenini, a top-rated dining destination in Verona. If you're in the mood to try something new, consider Osteria da Ugo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Locanda 4 Cuochi. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Verona this evening.

After enjoying a fulfilling meal, continue your evening at Duchi Café, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Cambridge Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Rubicone Caffe provides an excellent environment for a relaxed and enjoyable evening.

Celebrate another amazing day of your road trip adventure in Italy!

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Venice. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Verona allows for both. Start by heading to Bridge Of Sighs. This well-known monument provides an insightful glimpse into the city's identity. Next, discover Doge's Palace, an UNESCO world heritage-designated palace, promising a delightful encounter.

Continue your sightseeing with a visit to St Mark's Basilica, a notable church. When you’re done, don’t forget to make a stop at the underrated St Mark's Campanile. Not far away from the monument, you will find the romantic Rialto Bridge, perfect for a quick visit. Round off your day at Piazza San Marco, another gem in Verona with romantic features to discover.

When you’re done exploring for the day, you’ll drive to your hotel in Venice. Check in and spend some time relaxing before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat in Venice. 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.

Treat yourself to a delightful dinner at Bauer Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try L'Osteria Le Guglie? It's another excellent option with a diverse menu. Consider reserving a table at Corner Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Al Parlamento, known for its inviting atmosphere. The Caffe Rosso is another great option if you’re looking for a place to get the night started. Similarly, Adagio provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

Day 8 of your road trip will take you to the best attractions Venice has to offer. Cherish the 1 night you have left in Venice by discovering the best things there are to see and do in the city.

Don’t miss Cannaregio in Venice today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Immerse yourself in Venice’s rich culture with today's sightseeing itinerary. Start your journey at Santa Maria Della Salute. This culturally significant church is sure to ignite your curiosity. Next, dive into the history-steeped features of Peggy Guggenheim Collection, 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 Gallerie Dell'accademia, an underrated art gallery. For a change of scene, check out Santa Maria Gloriosa Dei Frari, known for its breathtaking features. We also recommend visiting Grand Canal. This street is a must for anyone looking to experience the city to the fullest.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Venice. 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.

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.

Extend your evening after a delightful meal by visiting Il Mercante, which offers the perfect atmosphere for a night out. Moreover, The Irish Pub Venezia is another popular option for a drink or two. Likewise, Ai Stagneri also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Savor another day of unforgettable experiences in Italy!

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 Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Today's adventure in Venice 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 Ponte Vecchio, another romantic attraction that never fails to captivate visitors. Next, head over to Uffizi Gallery, one of the city’s most famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Palazzo Vecchio. This visually striking palace is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Della Signoria, an astonishing public square, and take a stroll around the area.

At the end of the day, you will drive to Florence, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass and celebrate another amazing day of your road trip in Italy!

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most astonishing attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This history-steeped church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Dell'accademia and learn what makes this photogenic art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Leaning Tower Of Pisa. After exploring the monument, head to Pisa Cathedral. This often recommended church is a highlight in Florence. As your day continues, stop by Piazza Del Duomo, Pisa, known for its picture-perfect features.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

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.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Florence is home to plenty of attractions that offer fun adventures, picturesque spots, and history-rich sites! Start at Fontan Kontradi Sel'va, a frequently visited sightseeing destination that is worthwhile a visit in the city. Nearby, you’ll find Piccolomini Library, enchanting visitors with its heritage-rich appeal. Continue your exploration at Battistero Di San Giovanni Battista. This church is one of the city’s most increasingly popular spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Siena Cathedral. After exploring the church, head to the widely recognized Piazza Del Campo. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Tower Of Mangia, a place of historic interest in Florence.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you explore more of Siena, 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.

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 12 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience San Gimignano to the fullest today with this curated day itinerary!

Today’s agenda in Siena includes a monument, a museum, a public square, a park, a church and much more! Porta San Giovanni is must-visit monument and a great starting point for the day. Next, continue your journey to Sangimignano1300, a curiosity-inducing museum, located just a leisurely stroll away. Next, head to Palazzo Comunale, Pinacoteca, Torre Grossa, a picture-perfect museum, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the up-and-coming Piazza Del Duomo. If you’re looking for more, Parco Della Rocca is also an underrated attraction that is worthwhile a visit. Lastly, don’t miss Chiesa Di Sant'agostino, a place of photogenic interest in the village.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Fischi per Fiaschi? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Keep the evening going at Charlie Mixology Bar Di Aldinucci Riccardo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Pinacoteca, which offers a similarly pleasant setting and great drinks. Another option is San Paolo Pub, which provides an inviting environment for unwinding after a busy day out.

Get a good night's sleep and look forward to another great day on the road in Italy!

On day 13 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 4 destinations, Riomaggiore, Manarola, Corniglia, and Monterosso al Mare. When you’re not sightseeing, take time to relax at your selected hotel in Monterosso al Mare, where you’ll be staying for 1 night.

Prepare for a day full of fun adventures, romantic experiences, and natural wonders. When you’re ready, kick off your sightseeing adventure at Riomaggiore. This up-and-coming sightseeing destination is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Manarola Overlook Viewpoint, one of the village’s best highlights.

Next, check out Cinque Terre National Park, one of the most well-known places to see in Siena. This national park is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Parrocchia Di S. Giovanni Battista. Wander around and soak in the history-steeped atmosphere this church offers.

When you’re done exploring for the day, you’ll drive to your hotel in Monterosso al Mare. Check in and spend some time relaxing before you head out to tour the village.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Monterosso al Mare. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Pizzeria La Smorfia, a top recommendation for dinner tonight. Or, for a change of pace, La Taverna di Monterosso boasts a menu that's sure to impress. Also, be sure to check out Hotel Albergo Degli Amici. Known as a local hotspot, it’s a great choice for tonight in Monterosso al Mare.

Following your dinner, dive into the local bar culture at Enoteca Da Eliseo. Enjoy this evening's relaxed ambiance with delightful drinks.

Take some time to reflect on your day and savor another beautiful night in Italy.