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

Day 2 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in Milan by discovering the best things there are to see and do in the city.

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

Discover a day packed with fun adventures, romantic experiences, and scenic views in Milan. Begin your sightseeing with Duomo Di Milano Museum. This globally renowned church is one of the top attractions in the city. Proceed to Galleria Vittorio Emanuele Ii, 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 Sforzesco Castle Art Library. This spectacular castle is a traveler-favorite. Not far away, you’ll find Parco Sempione, another key site on your sightseeing itinerary. Piazza Gae Aulenti is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Don’t miss out on dining 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.

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

Savor another day of unforgettable experiences in Italy!

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Como, Rogaro, Lenno, and Colonno, 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 Como. You’ll stay here for 1 night.

Get ready for a day filled with fun adventures, photo-friendly spots, and historic treasures in the charming city of Milan. Your adventure starts at Basilica Di San Fedele, an up-and-coming local hot spot. Another notable attraction to explore is Saint Mary Assunta Cathedral. This locally renowned church is known for its monumental appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Villa Carlotta (lake Como). This history-steeped museum offers a fascinating experience that many visitors find memorable. Villa Del Balbianello is also worth visiting, along with Greenway Del Lago Di Como. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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 dinnertime approaches, it's time to head out for a bite to eat in Como. 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 L’Antica Trattoria, an iconic dining spot in Como. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Gesumin Restaurant, a popular restaurant in Como. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Pronobis, a hidden gem nestled in Como. 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. Fresco Cocktail Shop is an excellent place to start. You could also check out Bar Il Cortiletto, offering a different kind of charm. A last recommendation for the day is Bar Pinocchio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 4 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 1 night.

Brace yourself for today’s incredible lineup of attractions in Como, featuring fun adventures, romantic experiences, and natural wonders. Start at Giusti Garden, an increasingly popular botanical garden in the city. Then, head to Ponte Pietra and soak in the ambiance of this awe-inspiring historical landmark.

There are many interesting places to see in Como, and when you are ready for more, go to Piazza Dei Signori. This is one of the city’s most increasingly popular history-steeped spots of interest. After exploring the public square, visit the popular Piazza Delle Erbe. Not far away, you'll also find Castelvecchio Museum. This museum is a historic highlight in Como. Before wrapping up your self-guided sightseeing tour, head to Verona Arena, an iconic stadium in the city.

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

As you explore more of Verona, 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 delightful dinner at La Griglia, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Vecio Macello? It's another excellent option with a diverse menu. Consider reserving a table at Via Fama Cafè | Verona as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Verona.

Following your dinner, dive into the local bar culture at Archivio. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to La Segreteria Café, the perfect place for those looking to experience the best of the nightlife. Similarly, Grande Giove Cocktail Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Embark on another extraordinary experience on day 5 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.

Today’s agenda in Verona includes a church, an art gallery, and a street. Santa Maria Della Salute is must-visit church and a great starting point for the day. Next, continue your journey to Peggy Guggenheim Collection, a captivating art gallery, located just a leisurely stroll away. Next, head to Santa Maria Gloriosa Dei Frari, a grand church, also available for your discovery today.

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.

Treat yourself to a wonderful meal at Bauer Hotel, a top-rated dining spot in Venice. If you're in the mood for something new, try L'Osteria Le Guglie, another premier location with a delectable menu. You might also want to book a table at Corner Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Venice.

Cap off your dinner by heading to Al Parlamento, ideal for a leisurely evening with a drink in hand. The Caffe Rosso is another bar that offers an enjoyable setting. Similarly, Adagio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 6 of your road trip, you will have an entire day to explore Venice. You’ll stay in Venice for 1 night and discover all the best things to see and do in the area.

Savor the day by visiting some of the best places to see in Venice, including a historical landmark, an opera house, a public square, a church, a palace, a monument and much more! Start your adventure at Rialto Bridge. This world-famous historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Teatro La Fenice located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Piazza San Marco. Its romantic features will captivate you. After the public square, continue your tour of the city with a visit to St Mark's Basilica. Visitors usually appreciate the symbolic features of this church. Next up is Doge's Palace, a highly recommended palace. For a change of pace, head to Bridge Of Sighs. As one of the most interesting attractions in Venice, this monument is the perfect place to end your self-guided sightseeing tour.

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 lovely dining experience at Generator Venice, 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 Nevodi, 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 La Piazza. It’s yet another ideal choice to enhance your time in Venice tonight.

Explore the vibrant nightlife at Il Mercante after your meal, a hub for lively evenings and memorable moments. Or, head to The Irish Pub Venezia for a great selection of flavorful drinks and a charming setting. Furthermore, Ai Stagneri is perfect for those looking to extend their night with a touch of local flavor.

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

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 3 nights here for some well-deserved relaxation.

Start by visiting Piazzale Michelangelo, a prime spot to begin your journey. This history-steeped observation deck is sure to impress. Next on your list is Basilica Of Santa Croce In Florence, another must-visit landmark and locally renowned church renowned for its culturally significant features.

We also recommend visiting Central Market, a popular food market. Nearby, you'll also find Cathedral Of Santa Maria Del Fiore, ready to add charm to your journey.

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

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

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.

Raise your glass to another unforgettable day 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.

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood 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.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the wondrous Ponte Vecchio, a history-steeped historical landmark in Florence. Next, go to Piazza Della Signoria.

After visiting Ponte Vecchio and Piazza Della Signoria, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Bargello National Museum. This heritage-rich museum offers a unique experience. Palazzo Vecchio is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Uffizi Gallery, one of the most romantic places to visit 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.

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

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

On day 9 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 Pisa. You still have 1 night left in Florence.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Santa Maria Della Spina. This intriguing church provides an insightful glimpse into the city's identity. Next, discover Knights' Square, a breathtaking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Leaning Tower Of Pisa, a globally renowned monument. When you’re done, don’t forget to make a stop at the increasingly popular Pisa Cathedral. Not far away from the church, you will find the culturally significant Campo Santo, perfect for a quick visit. Round off your day at Piazza Del Duomo, Pisa, another gem in Florence with breathtaking features to discover.

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable 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 10 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 1 night.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Porta Romana. This historic monument is a highlight of any visit in the city. Then, enjoy Palazzo Salimbeni, another photogenic attraction that never fails to captivate visitors. Next, head over to Basilica Of San Domenico, one of the city’s most often recommended attractions, known for its historic features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This visually striking church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Pubblico Palace, an often recommended palace, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Campo 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.

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.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena 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!

Dive into day 11 of your remarkable road trip in Italy. Today you will explore Rome, 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 Rome. You’ll stay here for 3 nights.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most globally renowned attractions included on the itinerary is Colosseum. This picture-perfect archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Roman Forum and learn what makes this UNESCO world heritage-designated archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the widely recognized Piazza Del Popolo. After exploring the public square, head to Capitoline Museums. This notable museum is a highlight in Siena.

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.

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

Enjoy a lovely meal at La Bottega Roma, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Pasta In Corso is another top choice with a popular menu. You could also check for a table at Trattoria Vecchia Roma. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

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

Set aside time today to explore Trastevere, 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.

Discover a day packed with fun adventures, romantic experiences, and picturesque spots in Rome. Begin your sightseeing with Vatican Museums. This globally renowned art museum is one of the top attractions in the city. Proceed to Sistine Chapel, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to St. Peter's Basilica. This wondrous major basilica is a traveler-favorite. Not far away, you’ll find Campo De' Fiori, another key site on your sightseeing itinerary. Piazza Navona is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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.

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

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 13 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Start by visiting Basilica Of San Clemente, a prime spot to begin your journey. This eye-catching church is sure to impress. Next on your list is Spanish Steps, another must-visit landmark and top-rated public square renowned for its respected features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Di Spagna. This visually striking public square is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Trevi Fountain, a timeless monument. Nearby, you'll also find Pantheon, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Castel Sant'angelo and wrap up your day with its romantic appeal.

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.

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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

On day 14 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Milan, where you’ll be staying for 1 night.

Get ready to discover some of the most iconic wonders in Rome, including a church, a public square, and a monument. Start your day at Bologna Cathedral. This breathtaking church is an intriguing place to see in Rome. Then, wander over to Piazza Maggiore. If visually striking sites excite you, this public square will be right up your alley. Nearby, you’ll also find Two Towers. This culturally significant monument is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Porta Maggiore is an often recommended spot in the city that will captivate you with its unique charm.

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

Have a fantastic dining experience at Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

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

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