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 offers a multitude of experiences. You will stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

At the top of the list of things to do today is to explore Via Monte Napoleone, a street that captures the true essence of Milan. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions. Another must-visit is Brera, a neighborhood offering a different perspective on Milan.

Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a church, an opera house, and a shopping mall. Begin your adventure at Santa Maria Delle Grazie Church. This is a notable church you should not miss. Another must-see is La Scala, a well-known opera house in Milan.

When you’re ready for the next sight, head to Galleria Vittorio Emanuele Ii. From there, take a leisurely stroll to Duomo Di Milano Museum, another of the city’s world-famous attractions.

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.

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’re not ready to end the night just yet, Kilburn Cocktail Bar Milano offers a perfect venue to relax and savor a drink. Similarly, Bar Frida is well-suited for those looking to unwind in a social setting. The Friends Pub Milano is another excellent spot to enjoy a nightcap after a delightful meal.

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.

Get ready to discover some of the most iconic wonders in Milan, including a monument, a palace, a museum, a church and much more! Start your day at Faro Voltiano Di Brunate. This culturally significant monument is a worthwhile place to see in Milan. Then, wander over to Villa Olmo. If history-steeped sites excite you, this palace will be right up your alley. Nearby, you’ll also find Tempio Voltiano. This awe-inspiring museum is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Saint Mary Assunta Cathedral is a locally renowned spot in the hamlet that will captivate you with its unique charm.

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.

As you explore more of Como, 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 L’Antica Trattoria, a highly-rated dining destination in Como. If you're eager to try something different, consider Gesumin Restaurant, another top spot with a tantalizing menu. You might also want to secure a reservation at Pronobis. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Como this evening.

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

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

On day 4 of your road trip, you’ll start and end your day in Como, where you'll stay for 1 night more.

Today's adventure in Como promises more breathtaking discoveries and enriching experiences! Begin at I Giardini Di Villa Melzi. This romantic botanical garden is a highlight of any visit in the hamlet. Then, enjoy Lungolago Europa, another romantic attraction that never fails to captivate visitors. Next, head over to Orrido Di Bellano, one of the hamlet’s most popular attractions, known for its idyllic features.

If you’re looking for more, spend time soaking in the atmosphere of Villa Carlotta (lake Como). This visually striking museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co), a frequently visited church, and take a stroll around the area.

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

As you explore more of Como, 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 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.

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

Raise your glass to another unforgettable day in Italy!

On day 5 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 Verona. In the evening, you’ll end up in Verona, where you will stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Como, featuring fun adventures, romantic experiences, and scenic views. Start at Castel San Pietro, a frequently visited castle in the city. Then, head to Ponte Pietra and soak in the ambiance of this enchanting 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 interesting visually striking spots of interest. After exploring the public square, visit the popular Castelvecchio Museum. Not far away, you'll also find Castelvecchio Bridge. This monument is a history-steeped highlight in Como. Before wrapping up your self-guided sightseeing tour, head to Verona Arena, a wondrous stadium in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Verona. 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 Verona. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day'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.

Extend your evening after a delightful meal by visiting Archivio, which offers the perfect atmosphere for a night out. Moreover, La Segreteria Café is another popular option for a drink or two. Likewise, Grande Giove Cocktail Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Verona 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 Sirmione and Malcesine.

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Verona on today’s itinerary. First up is the locally renowned archeological site, Archaeological Site Of Grotte Di Catullo. Afterward, continue to Scaliger Castle, a castle every traveler should visit.

As you explore Verona’s charming streets, take in the lively atmosphere and get to know the character of the town. Next, make your way to Beach Brema Sirmione. This increasingly popular beach is an essential stop. Following that, head to Castle Of Malcesine, another must-visit site that will enhance your experience.

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

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 Trattoria I Masenini, a top pick for dinner tonight. Alternatively, Osteria da Ugo beckons with its unique menu offerings. Also, consider Locanda 4 Cuochi. With its consistent customer satisfaction, it’s an excellent option for dining in Verona tonight.

Continue your evening by exploring the vibrant nightlife scene at Duchi Café, a prime destination for a thrilling night out. Also, don’t forget to check out Cambridge Bar, a bar that offers unique local touches. Likewise, Rubicone Caffe provides an excellent alternative for a fun evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

Dive into day 7 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.

Bring your curiosity for today’s adventure around Verona. Some of the city’s most loved attractions await! Bridge Of Sighs is the perfect place to start. This monument is one of the most notable places to visit in Verona. Next, head to Doge's Palace, an interesting palace, known for its UNESCO world heritage-designated 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 St Mark's Basilica. This UNESCO world heritage-designated church is a highly recommended experience. Nearby, you'll also find St Mark's Campanile and Piazza San Marco. Visit these for an interesting touch to your journey. Finish the day with a visit to Rialto Bridge, a visually striking historical landmark in Verona.

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.

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 enjoying a fulfilling meal, continue your evening at Al Parlamento, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Caffe Rosso offers a welcoming atmosphere for easing into the nightlife. Similarly, Adagio provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!

On day 8 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.

Cannaregio is one of the highlights of today. Take your time exploring this iconic neighborhood in Venice, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Savor the day by visiting some of the best places to see in Venice, including a church, an art gallery, and a street. Start your adventure at Santa Maria Della Salute. This up-and-coming church is a must-visit for travelers looking for a unique holiday experience. Make your way to Peggy Guggenheim Collection located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Gallerie Dell'accademia. Its historic features will captivate you. After the art gallery, continue your tour of the city with a visit to Santa Maria Gloriosa Dei Frari. Visitors usually appreciate the picture-perfect features of this church. Next up is Grand Canal, a highly recommended street.

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

Dine in style at Generator Venice, a top recommendation for dinner tonight. Or, for a change of pace, Nevodi boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Piazza. Known as a local hotspot, it’s a great choice for tonight in Venice.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Il Mercante stands out as an excellent choice for a post-dinner cocktail. Alternatively, The Irish Pub Venezia offers an ideal atmosphere to enjoy the pleasures of the night. Ai Stagneri is also a great option that provides a perfect setting for a relaxing evening.

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

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Piazzale Michelangelo. This extraordinary observation deck is a visually striking place to see in Venice. Continue your discovery at Ponte Vecchio, a visually striking historical landmark with stories to tell.

As you stroll around Venice, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Uffizi Gallery. This widely recognized art gallery offers a picture-perfect encounter with Venice. Next, make your way to Palazzo Vecchio to add another highlight to your day. After that, visit Piazza Della Signoria, an impressive public square 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 Venice.

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.

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

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

On day 10 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 1 night more, there’s no need to rush. Experience Florence and Pisa to the fullest today with this curated day itinerary!

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Cathedral Of Santa Maria Del Fiore. This widely recognized church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Galleria Dell'accademia, one of the city’s best highlights.

Next, check out Leaning Tower Of Pisa, one of the most timeless places to see in Florence. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pisa Cathedral. Wander around and soak in the breathtaking atmosphere this church offers. Then, head to Piazza Del Duomo, Pisa, a top-rated public square that adds another dimension to your day.

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

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

Enjoy a delicious meal 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.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Celebrate another amazing day of your road trip adventure 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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Fontan Kontradi Sel'va. Next, dive into the eye-catching features of Piccolomini Library, a must-visit library 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 Battistero Di San Giovanni Battista, a beloved church. For a change of scene, check out Siena Cathedral, known for its visually striking features. We also recommend visiting Piazza Del Campo. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Tower Of Mangia, yet another frequently visited attraction in Florence.

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

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

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena 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!

Wake up to day 12 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s route brings family-friendly attractions, breathtaking views, and photo-friendly spots. The first attraction of today is Porta San Giovanni. This worthwhile monument is an UNESCO world heritage-listed place to see in Siena. Continue your discovery at Sangimignano1300, a heritage-rich museum with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Palazzo Comunale, Pinacoteca, Torre Grossa. This curiosity-inducing museum offers a breathtaking encounter with Siena. Next, make your way to Piazza Del Duomo to add another highlight to your day. After that, visit Parco Della Rocca, a frequently visited park that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Chiesa Di Sant'agostino, a frequently visited church in the village. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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

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

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

To truly maximize your evening out, consider visiting Charlie Mixology Bar Di Aldinucci Riccardo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Pinacoteca, another bar with an inviting ambiance. Similarly, San Paolo Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip 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.

A blend of family-friendly attractions, romantic experiences, and natural wonders await you in Siena on today’s itinerary. First up is the up-and-coming sightseeing destination, Riomaggiore. Afterward, continue to Manarola Overlook Viewpoint, an observation deck every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Cinque Terre National Park. This popular national park is an essential stop. Following that, head to Parrocchia Di S. Giovanni Battista, another must-visit site that will enhance your experience.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Monterosso al Mare. Monterosso al Mare 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 Monterosso al Mare. If you are looking to dine at a popular restaurant in the village, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Pizzeria La Smorfia, an excellent option for tonight's dining. Looking for something different? La Taverna di Monterosso offers a tantalizing alternative with its diverse menu. And don’t miss Hotel Albergo Degli Amici. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Monterosso al Mare.

Unwind after your meal by stepping into Enoteca Da Eliseo. This venue is celebrated for its extensive drink selections and cozy vibes.

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