Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

On day 2 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 1 night and discover all the best things to see and do in the area.

A top thing to do today is to explore Navigli, a must-see neighborhood in Milan. It's the perfect starting point for touring the top attractions in the area.

Milan is brimming with adventures. Today’s wonderful stops include a church, a shopping mall, a castle, a park, a public square and much more! Begin your sightseeing adventure at the timeless Duomo Di Milano Museum and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Vittorio Emanuele Ii, a visually striking shopping mall that draws visitors from far and near.

Continue your journey to Sforzesco Castle Art Library, one of the city’s most famous spots that you shouldn’t miss. Another great site to visit is the famous Parco Sempione. When you're finished at the park, Piazza Gae Aulenti awaits your visit. This public square is a breathtaking highlight on today's 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.

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

Enjoy a lovely meal at Dessert Bar Milano, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Radisson Blu Hotel Milan is another top choice with a popular menu. You could also check for a table at Ristorante Qui Si Mangia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

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

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

On day 3 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 Como, Rogaro, Lenno, and Colonno. In the evening, you’ll end up in Como, where you will stay for 1 night.

Prepare for a day full of fun adventures, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Basilica Di San Fedele. This often recommended church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Saint Mary Assunta Cathedral, one of the city’s best highlights.

Next, check out Villa Carlotta (lake Como), one of the most worthwhile places to see in Milan. This museum is a favorite among locals and travelers alike. Then, head to Greenway Del Lago Di Como, a top-rated hiking area that adds another dimension to your day.

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 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.

Cap off your dinner by heading to Fresco Cocktail Shop, ideal for a leisurely evening with a drink in hand. Bar Il Cortiletto is another bar that offers an enjoyable setting. Similarly, Bar Pinocchio is also a popular place to go on a night out, perfect for relaxing and socializing.

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.

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.

A blend of fun adventures, romantic experiences, and natural wonders await you in Como on today’s itinerary. First up is the locally appreciated botanical garden, Giusti Garden. Afterward, continue to Ponte Pietra, a historical landmark every traveler should visit.

As you explore Como’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Dei Signori. This up-and-coming public square is an essential stop. Following that, head to Piazza Delle Erbe, another must-visit site that will enhance your experience. Don’t forget to stop by Castelvecchio Museum, an interesting museum in the city. Finally, end your day with a visit to Verona Arena, an enchanting stadium that offers the perfect conclusion to your sightseeing of the day.

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.

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 lovely meal at La Griglia, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Vecio Macello is another top choice with a popular menu. You could also check for a table at Via Fama Cafè | Verona. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Verona tonight.

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

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

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Venice, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Venice. You’ll stay here for 2 nights.

Today’s itinerary in Verona covers several incredible sights, including a church, an art gallery, and a street. Start your adventure at Santa Maria Della Salute. This up-and-coming church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the awe-inspiring wonders of Peggy Guggenheim Collection, a must-see art gallery in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Santa Maria Gloriosa Dei Frari. This frequently visited church offers an enriching experience. For a change of pace, head to Grand Canal, where you can take in UNESCO world heritage-listed features. These sights offer a fulfilling end to a perfect day.

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.

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

Don’t miss out on dining at Bauer Hotel, a top-rated dining destination in Venice. If you're in the mood to try something new, consider L'Osteria Le Guglie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Corner Pub. 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 Al Parlamento, which offers the perfect atmosphere for a night out. Moreover, The Caffe Rosso is another popular option for a drink or two. Likewise, Adagio 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!

Day 6 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most world-famous attractions included on the itinerary is Rialto Bridge. This romantic historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Teatro La Fenice and learn what makes this picture-perfect opera house unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the wondrous Piazza San Marco. After exploring the public square, head to St Mark's Basilica. This interesting church is a highlight in Venice. As your day continues, stop by Doge's Palace, known for its visually striking features. Lastly, don’t forget to check out the interesting Bridge Of Sighs. Enjoy exploring this incredible monument at your own pace.

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.

Enjoy a delicious meal 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.

Unwind after your meal by stepping into Il Mercante. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, The Irish Pub Venezia offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Ai Stagneri, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 3 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Piazzale Michelangelo. This famous observation deck provides an insightful glimpse into the city's identity. Next, discover Basilica Of Santa Croce In Florence, a standout church, promising a delightful encounter.

Continue your sightseeing with a visit to David, an interesting statue. When you’re done, don’t forget to make a stop at the popular Central Market. Round off your day at Cathedral Of Santa Maria Del Fiore, another gem in Venice with UNESCO world heritage-listed features to discover.

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.

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 delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

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

Day 8 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Set aside time today to explore Oltrarno, 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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Ponte Vecchio. This visually striking historical landmark is a highlight of any visit in the city. Then, enjoy Piazza Della Signoria, another visually striking attraction that never fails to captivate visitors. Next, head over to Bargello National Museum, one of the city’s most often recommended attractions, known for its detailed features.

If you’re looking for more, spend time soaking in the atmosphere of Palazzo Vecchio. This grand palace is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Uffizi Gallery, an impressive art gallery, and take a stroll around the area.

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 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.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

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.

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

On day 9 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 Pisa to the fullest today with this curated day itinerary!

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a monument, a cemetery and much more! Start your adventure at Santa Maria Della Spina. This up-and-coming church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Knights' Square, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Leaning Tower Of Pisa. This wondrous monument offers an enriching experience. For a change of pace, head to Pisa Cathedral, where you can take in UNESCO world heritage-listed features. Conclude your self-guided sightseeing tour with a visit to Piazza Del Duomo, Pisa and Campo Santo. These sights offer a fulfilling end to a perfect day.

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

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

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Gosh*, known for its inviting atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another great option if you’re looking for a place to get the night started. Similarly, Quelo Bar provides a great setting to enjoy the night away.

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

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a palace, a church, a public square and much more! Begin your adventure at Porta Romana. This is a beloved monument you should not miss. Another must-see is Palazzo Salimbeni, a frequently visited palace in Florence.

When you’re ready for the next sight, head to Basilica Of San Domenico. From there, take a leisurely stroll to Siena Cathedral, another of the city’s interesting attractions. We recommend continuing your self-guided tour at Pubblico Palace, a historic place of interest in the city. If time allows, add Piazza Del Campo to your itinerary. This spectacular public square offers the perfect finishing touch to your day 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.

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.

Enjoy a lovely dining experience at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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 Rome. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Siena is home to plenty of attractions that offer family-friendly attractions, scenic views, and photo-friendly spots! Start at Colosseum, a timeless archeological site that is worthwhile a visit in the city. Nearby, you’ll find Roman Forum, enchanting visitors with its picture-perfect appeal. Continue your exploration at Piazza Del Popolo. This public square is one of the city’s most spectacular spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Capitoline Museums.

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

As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. 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, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

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

At the end of the day, you'll drive back to Rome, where you'll stay for 2 nights more.

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Vatican Museums.

If you’re looking for more, spend time soaking in the atmosphere of Campo De' Fiori. This picture-perfect public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Navona, a globally renowned public square, and take a stroll around the area.

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

As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

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

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Today’s route brings family-friendly attractions, photo-friendly spots, and historic treasures. The first attraction of today is Basilica Of San Clemente. This underrated church is a photogenic place to see in Rome. Continue your discovery at Spanish Steps, a romantic public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Di Spagna. This iconic public square offers a symbolic encounter with Rome. Next, make your way to Trevi Fountain to add another highlight to your day. After that, visit Pantheon, an iconic monument that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Castel Sant'angelo, an astonishing castle in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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 Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Continue your lively evening at The Apartment Bar Roma, a perfect place for winding down or revving up the night, depending on which mood you’re in. Hotel Hassler Roma is another excellent bar that offers a great selection of drinks to suit any mood.

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

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 1 night here for some well-deserved relaxation.

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the worthwhile Bologna Cathedral, a symbolic church in Rome. Next, go to Piazza Maggiore.

After visiting Bologna Cathedral and Piazza Maggiore, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Two Towers. This stunning monument offers a unique experience. Porta Maggiore is another noteworthy attraction worthwhile a visit.

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.

As you explore more of Milan, 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 Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

Continue the enjoyment post-dinner at Bhangrabar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Rufus Cocktail Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Ostello Bello Grande. 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 Milan and get some rest in preparation for another magical day of your road trip in Italy!