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

Day 2 offers an itinerary packed with the best things to see in Milan. You’ll stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

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

Check out the globally renowned church, Duomo Di Milano Museum. Afterward, continue to Galleria Vittorio Emanuele Ii, a shopping mall every traveler should visit. As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Sforzesco Castle Art Library. This impressive castle is an essential stop. Following that, head to Parco Sempione, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Gae Aulenti, a locally renowned public square in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Treat yourself to a delicious dinner at Dessert Bar Milano, an excellent option for tonight's dining. Looking for something different? Radisson Blu Hotel Milan offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Qui Si Mangia. Known for great service, it’s a fantastic choice for tonight in Milan.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass and celebrate another amazing day 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 4 places, which are Como, Rogaro, Lenno, and Colonno. At the end of the day, you will retreat to the hotel of your choice in Como, where will spend 1 night.

Como’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Milan behind. This drive usually takes around 1 hour 2 min. Como welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Basilica Di San Fedele. Spend some time admiring the culturally significant features of the church before you continue to your next stop. Then, head to Saint Mary Assunta Cathedral. This notable church is a traveler-favorite in the city.

Continue your road trip and head to your next destination, Rogaro. This car ride takes around 44 min.

Set out on a self-guided sightseeing tour at Villa Carlotta (lake Como) and explore the remarkable features.

When you’re done exploring for the day, you’ll drive to your hotel in Como. Check in and relax before you head out to tour the city.

Como is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Como.

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

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

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

Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Verona, where you'll spend 1 night.

After soaking in Como’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Verona. Expect your car journey to take a minimum of 2 hours 21 min. When you arrive in Verona, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Giusti Garden, a curiosity-inducing botanical garden that everyone visiting Verona should see. Next, head to Ponte Pietra. This enchanting historical landmark is one of the most popular attractions in the region.

If you're keen to see more, don’t miss out on Piazza Dei Signori, an enchanting public square popular among locals as well as travelers. Piazza Delle Erbe is an excellent attraction to visit next. Spend some time learning more about this locally renowned public square before you continue your journey. Lastly, visit Castelvecchio Museum, a picture-perfect museum and a top attraction in the city.

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

Indulge in a memorable dining experience at one of Verona's most popular restaurants, and connect with friendly locals for a true cultural experience.

Don’t miss out on dining at La Griglia, a top-rated dining destination in Verona. If you're in the mood to try something new, consider Vecio Macello, another top spot with a mouthwatering menu. You might also want to secure a reservation at Via Fama Cafè | Verona. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Verona this evening.

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

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

Dive into day 5 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Venice. At the end of the day, you’ll unwind at one of the finest accommodations in Venice, where you'll spend 2 nights.

Set your GPS to Venice and hit the road. Expect a journey of approximately 1 hour 49 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Venice beckons with new experiences!

For a more meaningful self-guided tour of the city's best attractions, visit Santa Maria Della Salute, an increasingly popular church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Peggy Guggenheim Collection and admire its noteworthy features.

When you’re ready, continue to Santa Maria Gloriosa Dei Frari, a curiosity-inducing church beloved by locals and tourists alike. Don't miss out on Grand Canal, another highlight of the area that promises a memorable visit.

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.

Enjoy a lovely dining experience at Bauer Hotel, a popular restaurant in Venice. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Venice at L'Osteria Le Guglie, 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 Corner Pub. It’s yet another ideal choice to enhance your time in Venice tonight.

Explore the vibrant nightlife at Al Parlamento after your meal, a hub for lively evenings and memorable moments. Or, head to The Caffe Rosso for a great selection of flavorful drinks and a charming setting. Furthermore, Adagio is perfect for those looking to extend their night with a touch of local flavor.

Savor another day of unforgettable experiences in Italy!

On day 6 of your road trip, you will have an entire day to discover what to see in Venice. You’ll stay in Venice for 1 night.

Visiting Rialto Bridge is always a good idea. This iconic historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Teatro La Fenice, a must-see opera house 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 Piazza San Marco. This globally renowned public square offers an enriching experience. For a change of pace, head to St Mark's Basilica, where you can take in inviting features. Conclude your self-guided sightseeing tour with a visit to Doge's Palace and Bridge Of Sighs These sights offer a fulfilling end to a perfect day.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

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.

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

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

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Florence may take around 2 hours 54 min. Upon your arrival in Florence, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Our first attraction recommendation in Florence is Piazzale Michelangelo, a top-rated observation deck that draws attention for its respected features. Spend some time soaking in the atmosphere before continuing to Basilica Of Santa Croce In Florence, a heritage-rich church that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to David, an interesting statue that offers a unique experience. Be sure to also explore Central Market, a nearby food market, highly recommended by other travelers. End your self-guided tour at Cathedral Of Santa Maria Del Fiore, a history-steeped church and the perfect final attraction in Florence.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

Day 8 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Florence.

Florence is brimming with adventures. Oltrarno is a neighborhood that stands out as one of the must-see places in Florence. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

One of the most timeless attractions included on the itinerary is Ponte Vecchio. This visually striking historical landmark will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Della Signoria and learn what makes this enchanting public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the underrated Bargello National Museum. After exploring the museum, head to Palazzo Vecchio. This notable palace is a highlight in Florence. As your day continues, stop by Uffizi Gallery, known for its eye-catching features.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Don’t miss out on dining 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 your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Greet day 9 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Pisa.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 14 min.

Our first attraction recommendation in Pisa is Santa Maria Della Spina, an up-and-coming church that draws attention for its visually striking features. Spend some time soaking in the atmosphere before continuing to Knights' Square, a culturally significant public square that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Leaning Tower Of Pisa, a wondrous monument that offers a unique experience. Be sure to also explore Pisa Cathedral, a nearby church, highly recommended by other travelers. End your self-guided tour at Piazza Del Duomo, Pisa, a picture-perfect public square and the perfect final attraction in Pisa.

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

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 10 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 12 min.

When you're ready for some sights, head to Porta Romana, an increasingly popular monument in Siena. Explore its culturally significant features at your own pace before you continue your journey to your next attraction, Palazzo Salimbeni. This worthwhile palace is a top recommendation in the area.

When you’re ready to explore more, Basilica Of San Domenico is an excellent choice. Spend some time discovering what some claim to be the most stunning church in the region. Next, continue your sightseeing at the captivating Siena Cathedral and discover what makes this church unique. If you’re up for one more stop in the city, head to Pubblico Palace, a historic palace many travelers find the visit worthwhile.

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

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

Enjoy a delicious meal 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.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 3 nights.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 2 hours 42 min, without any stops or traffic disruptions.

Spend your afternoon discovering Colosseum, a globally renowned archeological site known for its picture-perfect features. Next, continue your sightseeing at Roman Forum, a timeless archeological site.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Del Popolo and uncover the details of this enchanting public square. Make sure to also explore Capitoline Museums, a notable museum.

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.

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

Savor the flavors at La Bottega Roma, a top pick for dinner tonight. Alternatively, Pasta In Corso beckons with its unique menu offerings. Also, consider Trattoria Vecchia Roma. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Wake up to day 12 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Vatican City and Rome. With 2 nights to stay in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

At the top of the list of things to do today is to explore Trastevere, a neighborhood that captures the true essence of Vatican City. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Campo De' Fiori makes a great addition to your morning plans. This spectacular public square is a standout place to see in Rome. Continue your discovery at Piazza Navona, a visually striking public square with stories to tell.

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.

It’s time to gear up for the next part of your road trip adventure. Set course for Vatican City! Under favorable conditions, your drive to Vatican City may take around 12 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Savor the day by heading to Vatican Museums, a wondrous art museum that draws visitors from near and far.

Next, explore St. Peter's Basilica, yet another iconic place to see in the area.

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

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

Enjoy a delicious meal at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

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

Day 13 of your road trip across Italy promises a magnificent time exploring what to see in Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Let Basilica Of San Clemente set the tone for the day. Spend some time admiring this culturally significant church before continuing your journey. Spanish Steps is your next stop. This widely recognized public square is one of the best-rated sights in Rome.

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 Piazza Di Spagna. This visually striking public square is a sight to behold. To round off your sightseeing experience, visit Trevi Fountain and Pantheon. If time allows, end your day with Castel Sant'angelo, a visually striking castle that offers a memorable conclusion to your exploration.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Rome, 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.

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

Your itinerary for day 14 of your road trip in Italy includes 1 stop and features some of the highlights of Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

Fasten your seatbelt and make your way to your next stop — Bologna, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Bologna may take around 4 hours 15 min without traffic disruptions. Upon arrival in Bologna, we highly recommend checking out some of the top attractions.

Set out on a self-guided sightseeing tour at Bologna Cathedral and explore the respected features. Next, make your way to Piazza Maggiore, another highlight in Bologna. When you’re done exploring the public square, continue to Two Towers, a breathtaking monument.

Nearby, you will also find Porta Maggiore. This often recommended monument is a top place to see in the area.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and relax before you head out to tour the city.

Milan is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Milan.

Treat yourself to a delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 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, Bhangrabar offers a perfect venue to relax and savor a drink. Similarly, Rufus Cocktail Bar is well-suited for those looking to unwind in a social setting. Ostello Bello Grande is another excellent spot to enjoy a nightcap after a delightful meal.

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