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.

A visit to Via Monte Napoleone in Milan is a must on the agenda today. This street is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights. Don’t forget to check out Brera as well, a neighborhood that adds another layer to your exploration.

Discover a day packed with family-friendly attractions, picturesque spots, and historic treasures in Milan. Begin your sightseeing with Santa Maria Delle Grazie Church. This locally renowned church is one of the top attractions in the city. Proceed to La Scala, 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 Galleria Vittorio Emanuele Ii. This astonishing shopping mall is a traveler-favorite. Not far away, you’ll find Duomo Di Milano Museum, another key site on your sightseeing itinerary.

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 Galleria Vittorio Emanuele II. Take a leisurely stroll through unique and high-end shops, where local treasures are waiting to be found. Beyond shopping, Galleria Vittorio Emanuele II offers more options, including unique attractions, key services, and vibrant events.

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

Enjoy a lovely dining experience at Dessert Bar Milano, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Radisson Blu Hotel Milan, 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 Qui Si Mangia. It’s yet another ideal choice to enhance your time in Milan tonight.

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

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

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 3 vibrant destinations - San Maurizio, Tavernola, and Como. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Como. You will spend 2 nights here for some well-deserved relaxation.

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Milan on today’s itinerary. First up is the curiosity-inducing monument, Faro Voltiano Di Brunate. Afterward, continue to Villa Olmo, a palace every traveler should visit.

As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the hamlet. Next, make your way to Tempio Voltiano. This curiosity-inducing museum is an essential stop. Following that, head to Saint Mary Assunta Cathedral, 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 Como. Como 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 Como. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

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

Relax and recharge in preparation for another adventurous day in Italy!

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

Como is home to plenty of attractions that offer fun adventures, romantic experiences, and natural wonders! Start at I Giardini Di Villa Melzi, a frequently visited botanical garden that is worthwhile a visit in the hamlet. Nearby, you’ll find Lungolago Europa, enchanting visitors with its romantic appeal. Continue your exploration at Orrido Di Bellano. This canyon is one of the hamlet’s most interesting spots.

Enjoy the freedom of exploring Como at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Villa Carlotta (lake Como). After exploring the museum, head to the increasingly popular Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co).

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

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

Enjoy a delicious meal at Alle Terrazze Como, a highly-rated dining destination in Como. If you're eager to try something different, consider La Vita è Bella Ristorante - Insalateria, another top spot with a tantalizing menu. You might also want to secure a reservation at Sant'Anna. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Como this evening.

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.

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 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Verona. When you’re not sightseeing, take time to relax at your selected hotel in Verona, where you’ll be staying for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Como, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Castel San Pietro, an often recommended 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 notable history-steeped spots of interest. After exploring the public square, visit the locally renowned Castelvecchio Museum. Not far away, you'll also find Castelvecchio Bridge. This monument is a romantic highlight in Como. Before wrapping up your self-guided sightseeing tour, head to Verona Arena, a world-famous 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 dinnertime approaches, it's time to head out for a bite to eat in Verona. 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 Griglia, a highly-rated dining destination in Verona. If you're eager to try something different, consider Vecio Macello, another top spot with a tantalizing menu. You might also want to secure a reservation at Via Fama Cafè | Verona. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Verona this evening.

Cap off your dinner by heading to Archivio, ideal for a leisurely evening with a drink in hand. La Segreteria Café is another bar that offers an enjoyable setting. Similarly, Grande Giove Cocktail Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

Take some time to reflect on your day and savor another beautiful night 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Verona allows for both. Start by heading to Archaeological Site Of Grotte Di Catullo. This well-known archeological site provides an insightful glimpse into the town's identity. Next, discover Scaliger Castle, a visually striking castle, promising a delightful encounter.

Continue your sightseeing with a visit to Beach Brema Sirmione, an often recommended beach. When you’re done, don’t forget to make a stop at the interesting Castle Of Malcesine.

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

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.

Have a fantastic dining experience at Trattoria I Masenini, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria da Ugo offers an enticing alternative with its varied menu. Additionally, Locanda 4 Cuochi is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Verona.

To truly maximize your evening out, consider visiting Duchi Café after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Cambridge Bar, another bar with an inviting ambiance. Similarly, Rubicone Caffe also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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 popular places to visit in Verona. Next, head to Doge's Palace, a well-known palace, known for its romantic 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 visually striking 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 respected historical landmark in Verona.

At the end of the day, you will drive to Venice, 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 Venice, 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.

Savor the flavors at Bauer Hotel, a top pick for dinner tonight. Alternatively, L'Osteria Le Guglie beckons with its unique menu offerings. Also, consider Corner Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

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.

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.

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.

Set aside time today to explore Cannaregio, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

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 instagrammable 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 historic 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.

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

Savor the flavors at Generator Venice, a top pick for dinner tonight. Alternatively, Nevodi beckons with its unique menu offerings. Also, consider Ristorante La Piazza. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

Continue your lively evening at Il Mercante, a perfect place for winding down or revving up the night, depending on which mood you’re in. The Irish Pub Venezia is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Ai Stagneri ensures a night out tailored to your taste.

Say good night to Venice and look forward to another great day of your road trip in Italy!

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Florence, 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 Florence. You’ll stay here for 2 nights.

Savor the day by visiting some of the best places to see in Venice, including an observation deck, a historical landmark, an art gallery, a palace, a public square and much more! Start your adventure at Piazzale Michelangelo. This top-rated observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Ponte Vecchio located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Uffizi Gallery. Its romantic features will captivate you. After the art gallery, continue your tour of the city with a visit to Palazzo Vecchio. Visitors usually appreciate the enchanting features of this palace. Next up is Piazza Della Signoria, a highly recommended public square.

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

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

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass to another unforgettable day in Italy!

On day 10 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Florence and Pisa. You still have 1 night left in Florence.

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Florence on today’s itinerary. First up is the impressive church, Cathedral Of Santa Maria Del Fiore. Afterward, continue to Galleria Dell'accademia, an art gallery every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Leaning Tower Of Pisa. This iconic monument is an essential stop. Following that, head to Pisa Cathedral, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Duomo, Pisa, a timeless public square in the city.

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

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

On day 11 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. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Fontan Kontradi Sel'va. Then, enjoy Piccolomini Library, another history-steeped attraction that never fails to captivate visitors. Next, head over to Battistero Di San Giovanni Battista, one of the city’s most curiosity-inducing attractions, known for its heritage-rich features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This history-steeped church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Campo, a spectacular public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Tower Of Mangia before you head back to your hotel.

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.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

Say good night to Siena and look forward to another great day of your road trip in Italy!

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!

Set out on a day brimming with family-friendly attractions, scenic views, and photo-friendly spots. Start at the up-and-coming Porta San Giovanni, a historic monument in Siena. Next, go to Sangimignano1300.

After visiting Porta San Giovanni and Sangimignano1300, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Palazzo Comunale, Pinacoteca, Torre Grossa. This picture-perfect museum offers a unique experience. Piazza Del Duomo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Parco Della Rocca, one of the most romantic places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by Chiesa Di Sant'agostino.

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

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 lovely dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub 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!

Experience an unparalleled adventure on day 13 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 4 vibrant destinations - Riomaggiore, Manarola, Corniglia, and Monterosso al Mare. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Monterosso al Mare. You will spend 1 night here for some well-deserved relaxation.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most locally appreciated attractions included on the itinerary is Riomaggiore. Then, take a leisurely stroll to Manarola Overlook Viewpoint and learn what makes this peaceful observation deck unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Cinque Terre National Park. After exploring the national park, head to Parrocchia Di S. Giovanni Battista. This increasingly popular church is a highlight in Siena.

At the end of the day, you will drive to Monterosso al Mare, 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 Monterosso al Mare's most popular restaurants, and connect with friendly locals for an authentic adventure.

Make sure to reserve a table at Pizzeria La Smorfia, an iconic dining spot in Monterosso al Mare. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Taverna di Monterosso, a popular restaurant in Monterosso al Mare. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Hotel Albergo Degli Amici, a hidden gem nestled in Monterosso al Mare. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Enoteca Da Eliseo, where the evening is just getting started.

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