14-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Venice, Padua, Siena, Rome, Florence, and Pisa

Day 2 offers a multitude of experiences. You will stay in Milan for 2 nights more, offering you enough time to explore at a relaxed pace.

Immerse yourself in Milan’s rich culture with today's sightseeing itinerary. Start your journey at Parco Sempione. This mesmerizing park is sure to ignite your curiosity. Next, dive into the historic features of Sforzesco Castle Art Library, a must-visit castle in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to La Scala, a notable opera house. For a change of scene, check out Galleria Vittorio Emanuele Ii, known for its enchanting features. We also recommend visiting Duomo Di Milano Museum. This church is a must for anyone looking to experience the city to the fullest.

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 Milan's best restaurants.

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and modern cuisine in the city.

Cap off your dinner by heading to Kilburn Cocktail Bar Milano, ideal for a leisurely evening with a drink in hand. Bar Frida is another bar that offers an enjoyable setting. Similarly, The Friends Pub Milano is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Milan for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Milan and Sirmione.

Set out on a day brimming with family-friendly attractions, picturesque spots, and historic treasures. Start at the interesting Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a respected museum in Milan. Next, go to Beach Brema Sirmione.

After visiting Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" and Beach Brema Sirmione, have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to Scaliger Castle. This majestic castle offers a unique experience. Archaeological Site Of Grotte Di Catullo is another noteworthy attraction worthwhile a visit.

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

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.

Savor the flavors at Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

Continue your lively evening at Bhangrabar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Rufus Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Ostello Bello Grande ensures a night out tailored to your taste.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Verona. 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 1 night.

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await! Castelvecchio Museum is the perfect place to start. This museum is one of the most popular places to visit in Milan. Next, head to Verona Arena, a timeless stadium, known for its visually striking features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Delle Erbe. This romantic public square is a highly recommended experience. Nearby, you'll also find Museo Archeologico Al Teatro Romano. Visit these for an interesting touch to your journey.

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

As you explore more of Venice, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Experience a harmony of flavors at Local in Venice by securing a reservation in advance. Known for its 1-star Michelin status, Local offers a delightful variety of dishes highlighting its delicious contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Wistèria, a highly recommended restaurant known for its enticing contemporary and venetian cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Quadri, a highly acclaimed restaurant celebrated for its exceptional modern menu.

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

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

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

Venice is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Rialto Bridge, an iconic historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Piazza San Marco, enchanting visitors with its history-steeped appeal. Continue your exploration at St Mark's Basilica. This church is one of the city’s most popular spots.

Enjoy the freedom of exploring Venice at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Doge's Palace. After exploring the palace, head to the notable Bridge Of Sighs.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Padua. Padua 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 Padua. 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 Veganda, an iconic dining spot in Padua. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Ai Scarponi, a popular restaurant in Padua. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bamboo Cafe (Mma Silvestrin Snc Di Matteo & C), a hidden gem nestled in Padua. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Il Gottino - Wine Bar, where the evening is just getting started. In the same way, Brutal offers a unique charm perfect for experiencing the local bar scene in Padua. Al Buscaglione is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Padua and Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Start by visiting Ragione Palace, a prime spot to begin your journey. This picture-perfect palace is sure to impress. Next on your list is The Basilica Of St. Anthony, another must-visit landmark and captivating church renowned for its inviting features.

While exploring and sightseeing, take time to savor the culture of Padua by sampling some local delicacies. When you’re ready for more sightseeing, head to Two Towers. This breathtaking monument is an essential place to visit for anyone looking for the full Padua experience. We also recommend visiting Piazza Maggiore, an impressive public square.

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

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

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.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!

On day 7 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 Vatican City. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

The first attraction of today is Sistine Chapel.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Saint Peter's Square. Next, make your way to Vatican Museums to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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.

Treat yourself to an extraordinary dining experience at La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated establishment with 2 Michelin star, it is an ideal choice for mediterranean and creative cuisine in the city.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

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

Today’s itinerary in Rome covers several incredible sights, including a monument and a public square. Start your adventure at Altare Della Patria. This notable monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Trevi Fountain, a must-see monument 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 Di Spagna. This iconic public square offers an enriching experience. For a change of pace, head to Spanish Steps, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Piazza Del Popolo. These sights offer a fulfilling end to a perfect day.

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

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.

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.

Savor another day of unforgettable experiences in Italy!

Day 9 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.

Prepare for a day full of family-friendly attractions, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Circus Maximus. This locally renowned archeological site is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Largo Di Torre Argentina, one of the city’s best highlights.

Next, check out Pantheon, one of the most iconic places to see in Rome. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Campo De' Fiori. Wander around and soak in the historic atmosphere this public square offers. Then, head to Castel Sant'angelo, a top-rated castle that adds another dimension to your day.

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 Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Don’t miss out on dining at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

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

Dive into day 10 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 Florence. You’ll stay here for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, breathtaking views, and picturesque spots. Start at Roman Forum, a wondrous archeological site in the city. Then, head to Colosseum and soak in the ambiance of this culturally significant archeological site.

There are many interesting places to see in Rome, and when you are ready for more, go to Piazza Navona. This is one of the city’s most timeless visually striking spots of interest. After exploring the public square, visit the widely recognized Villa Borghese. Not far away, you'll also find Auditorium Parco Della Musica. This concert hall is an instagrammable highlight in Rome.

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.

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 11 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Today, you'll explore some of the most beautiful places in Florence, including a public square, a palace, an art gallery, a historical landmark, an observation deck and much more! Start your day with a visit to Piazza Della Signoria. This widely recognized public square is a must-visit in the city. When you’re ready for your next discovery, continue to Palazzo Vecchio, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Uffizi Gallery, a famous art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Ponte Vecchio and Piazzale Michelangelo.

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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery 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!

Embark on another extraordinary experience on day 12 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Of Santa Croce In Florence. This heritage-rich church is sure to ignite your curiosity. Next, dive into the visually striking features of Cathedral Of Santa Maria Del Fiore, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Galleria Dell'accademia, a locally renowned art gallery. For a change of scene, check out Central Market, known for its photogenic features.

When you’re done exploring for the day, you’ll drive to your hotel in Pisa. 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 Pisa. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at il Mercante, 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 La Ghiotteria. It’s yet another ideal choice to enhance your time in Pisa tonight.

If you’re not ready to end the night just yet, Jeffer Cocktails & Friends offers a perfect venue to relax and savor a drink. Similarly, Le Parisien Wine Bar is well-suited for those looking to unwind in a social setting. Las Volta Cocktailbar is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 13 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Genoa. 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 itinerary in Pisa covers several incredible sights, including a monument, a public square, a church, a beach and much more! Start your adventure at Leaning Tower Of Pisa. This world-famous monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the UNESCO world heritage-listed wonders of Piazza Del Duomo, Pisa, 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 Pisa Cathedral. This frequently visited church offers an enriching experience. For a change of pace, head to Spiaggia Pubblica Di Priaruggia, where you can take in peaceful features. These sights offer a fulfilling end to a perfect day.

At the end of the day, you will drive to Milan, 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 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 Ristorante la Brisa, a top-rated dining spot in Milan. If you're in the mood for something new, try Pasticceria San Carlo, another premier location with a delectable menu. You might also want to book a table at UNAHOTELS Cusani Milano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

Keep the evening going at Qc Termemilano, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yguana Cafè, which offers a similarly pleasant setting and great drinks.

Raise your glass to another unforgettable day in Italy!