11-Day Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, and San Gimignano

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.

One of the most iconic places you can visit today in Milan is Navigli. Allow yourself some time to leisurely explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Discover a day packed with fun adventures, romantic experiences, and natural wonders in Milan. Begin your sightseeing with Parco Sempione. This famous park is one of the top attractions in the city. Proceed to Sforzesco Castle Art Library, another must-visit attraction that enhances the city’s allure.

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 impressive 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 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 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 top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Round off your dining experience by visiting Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Rogaro, Lenno, and Colonno. When you’re not sightseeing, take time to relax at your selected hotel in Como, where you’ll be staying for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and natural wonders. Start at the interesting Orrido Di Bellano, an eye-catching canyon in Milan. Next, go to Botanical Garden Of Villa Carlotta.

After visiting Orrido Di Bellano and Botanical Garden Of Villa Carlotta, take time to explore Milan's streets and absorb its charm. Continue your sightseeing by heading to Villa Carlotta (lake Como). This visually striking museum offers a unique experience. Villa Del Balbianello is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Greenway Del Lago Di Como, one of the most eye-catching places to visit in Milan.

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.

Treat yourself to a wonderful meal at La Vita è Bella Ristorante - Insalateria, a top-rated dining spot in Como.

Unwind after your meal by stepping into Fresco Cocktail Shop. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Il Cortiletto offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Pinocchio, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

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

Enjoy the perfect balance of relaxation and exploration in Como today. One of the most well-known attractions included on the itinerary is Ponte Pietra. This romantic historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Delle Erbe and learn what makes this romantic public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Verona Arena. After exploring the stadium, head to Castelvecchio Museum. This captivating museum is a highlight in Como. Lastly, don’t forget to check out the interesting Castelvecchio Bridge. Enjoy exploring this incredible monument at your own pace.

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 lovely dining experience at La Griglia, a popular restaurant in Verona. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Verona at Vecio Macello, 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 Via Fama Cafè | Verona. It’s yet another ideal choice to enhance your time in Verona tonight.

Continue the enjoyment post-dinner at Archivio, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, La Segreteria Café offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Grande Giove Cocktail Bar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Embark on another extraordinary experience on day 6 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 Florence, which will be your home away from home for 3 nights.

Today's adventure in Venice promises more breathtaking discoveries and enriching experiences! Begin at Santa Maria Gloriosa Dei Frari. This stunning church is a highlight of any visit in the city. Then, enjoy Gallerie Dell'accademia, another history-steeped attraction that never fails to captivate visitors. Next, head over to Peggy Guggenheim Collection, one of the city’s most well-known attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Santa Maria Della Salute. This visually striking church is frequented by locals and tourists alike. To complete your memorable day, make sure to 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.

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 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.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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

Day 7 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in Florence by discovering the best things there are to see and do in the city.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Cathedral Of Santa Maria Del Fiore. This extraordinary church is a visually striking place to see in Florence. Continue your discovery at Piazza Della Signoria, an enchanting public square with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Ponte Vecchio. This globally renowned historical landmark offers an enchanting encounter with Florence. Uffizi Gallery is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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 Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

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.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 8 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Prepare for a day full of family-friendly attractions, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo, Pisa. This iconic public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Pisa Cathedral, one of the city’s most promising highlights.

Next, check out Leaning Tower Of Pisa, one of the most wondrous 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, St Martin Cathedral. Wander around and soak in the stunning atmosphere this church offers. Finally, take the path to the popular Piazza Dell'anfiteatro, the last of our attraction recommendations for today.

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

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.

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Extend your evening after a delightful meal by visiting Gosh*, which offers the perfect atmosphere for a night out. Moreover, Antico Caffè Del Moro - Art Bar Firenze is another popular option for a drink or two. Likewise, Quelo Bar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Celebrate another amazing day of your road trip adventure 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 Siena and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.

Get ready for a day filled with fun adventures, scenic views, and photo-friendly spots in the charming city of Florence. Your adventure starts at Fortezza Medicea (siena), a beloved local hot spot. Another notable attraction to explore is Piazza Del Campo. This impressive public square is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Siena Cathedral. This romantic church offers a fascinating experience that many visitors find memorable. Chiesa Di Sant'agostino is also worth visiting, along with Piazza Del Duomo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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

With its reputation for pleasing customers, it’s a fantastic choice for tonight in San Gimignano.

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

On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Castellina in Chianti and Greve in Chianti. When you’re not sightseeing, take time to relax at your selected hotel in Milan, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore San Gimignano on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Rocca Di Castellina In Chianti is the first of them. Spend some time admiring this romantic castle before continuing your journey. Tumulo Di Montecalvario is your next stop. This increasingly popular archeological site is one of the best-rated sights in San Gimignano.

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 Il Molino Di Grace. This eye-catching winery is a sight to behold. To round off your sightseeing experience, visit Castle Of Verrazzano.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Milan. Milan 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 Milan's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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!