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

On day 2 of your road trip in Italy, you’ll start and end your day in Trieste, but spend the day exploring what’s beyond the city. Since you will return to Trieste for 1 night more, there’s no need to rush. Experience Miramare / Miramar and Trieste to the fullest today with this curated day itinerary!

Brace yourself for today’s incredible lineup of attractions in Trieste, featuring fun adventures, romantic experiences, and scenic views. Start at Miramare Castle, an interesting castle in the village. Then, head to Canale Ponterosso Trieste and soak in the ambiance of this visually striking street.

There are many interesting places to see in Trieste and when you are ready for more, go to Piazza Della Borsa. This is one of the village’s most up-and-coming spots. After exploring the public square, visit the locally renowned Piazza Unità D'italia. Before wrapping up your self-guided sightseeing tour, head to the up-and-coming Revoltella Museum, an up-and-coming museum in the village.

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

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

Enjoy a delicious meal at Rustiko, a top-rated dining destination in Trieste. If you're in the mood to try something new, consider Caffè San Marco, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria Marise. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Trieste this evening.

If you’re not ready to end the night just yet, Mast offers a perfect venue to relax and savor a drink. Similarly, Urbanis is well-suited for those looking to unwind in a social setting. Coktail Bar Trieste | La Preferita is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day 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 1 vibrant destinations - Venice. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Venice. You will spend 2 nights here for some well-deserved relaxation.

Enjoy the perfect balance of relaxation and exploration in Trieste today. One of the most popular attractions included on the itinerary is Bridge Of Sighs. This enchanting monument will help you start your sightseeing on top. Then, take a leisurely stroll to Doge's Palace and learn what makes this romantic palace unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the interesting St Mark's Basilica. After exploring the church, head to Piazza San Marco. This globally renowned public square is a highlight in Trieste. Lastly, don’t forget to check out the intriguing Grand Canal. Enjoy exploring this incredible street at your own pace.

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

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 Bauer Hotel, a highly-rated dining destination in Venice. If you're eager to try something different, consider L'Osteria Le Guglie, another top spot with a tantalizing menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

If you’re not ready to end the night just yet, Al Parlamento offers a perfect venue to relax and savor a drink. Similarly, The Caffe Rosso is well-suited for those looking to unwind in a social setting. Adagio is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences in Italy!

Wake up to day 4 of your extraordinary road trip in Italy. With 1 night left in Venice, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

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

Venice is brimming with adventures. Today’s wonderful stops include a handicraft store, a church, and an art gallery. Begin your sightseeing adventure at the underrated Murano. Just a short distance away is Santa Maria Gloriosa Dei Frari, a symbolic church that draws visitors from far and near.

Continue your journey to Gallerie Dell'accademia, one of the village’s most underrated spots that you shouldn’t miss. Another great site to visit is the captivating Peggy Guggenheim Collection. Last up on today’s itinerary is a church. Make your way to Santa Maria Della Salute for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Venice.

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

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.

Treat yourself to a delicious dinner at Generator Venice, an excellent option for tonight's dining. Looking for something different? Nevodi offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante La Piazza. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

Keep the evening going at Il Mercante, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Irish Pub Venezia, which offers a similarly pleasant setting and great drinks. Another option is Ai Stagneri, which provides an inviting environment for unwinding after a busy day out.

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

On day 5 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 Verona. In the evening, you’ll end up in Verona, where you will stay for 2 nights.

Today’s route brings fun adventures, romantic experiences, and natural wonders. The first attraction of today is Giusti Garden. This up-and-coming botanical garden is an idyllic place to see in Venice. Continue your discovery at Ponte Pietra, an enchanting historical landmark with stories to tell.

As you stroll around Venice, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Delle Erbe. This well-known public square offers a romantic encounter with Venice. Next, make your way to Verona Arena to add another highlight to your day. After that, visit Fontana Di Piazza Bra, a worthwhile public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Castelvecchio Museum, a locally renowned museum 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 Venice.

At the end of the day, you will drive to Verona, 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 Verona. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at La Griglia, an iconic dining spot in Verona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Vecio Macello, a popular restaurant in Verona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Via Fama Cafè | Verona, a hidden gem nestled in Verona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Archivio, a great choice for enjoying the after-dinner hours with a drink. You could also go to La Segreteria Café, which offers a similarly pleasant setting and great drinks. Another option is Grande Giove Cocktail Bar, which provides an inviting environment for unwinding after a busy day out.

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 Verona, where you'll stay for 1 night more.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the notable Archaeological Site Of Grotte Di Catullo, a history-steeped archeological site in Verona. Next, go to Scaliger Castle.

After visiting Archaeological Site Of Grotte Di Catullo and Scaliger Castle, take time to explore Verona's streets and absorb its charm. Continue your sightseeing by heading to Castello Di Desenzano Del Garda. This instagrammable castle offers a unique experience. Porta Brescia is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Escape From Atlantis, one of the most awe-inspiring places to visit in Verona.

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

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

Have a fantastic dining experience at Trattoria I Masenini, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria da Ugo offers an enticing alternative with its varied menu. Additionally, Locanda 4 Cuochi is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Verona.

Keep the excitement of the evening going by visiting a bar or two. Duchi Café is an excellent place to start. You could also check out Cambridge Bar, offering a different kind of charm. A last recommendation for the day is Rubicone Caffe. 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.

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Milan. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 2 nights.

Get ready for an exciting day in Verona. Today’s sightseeing agenda includes an opera house, a shopping mall, and a church. Begin your adventure at La Scala. This is a notable opera house you should not miss. Another must-see is Galleria Vittorio Emanuele Ii, a top-rated shopping mall in Verona.

When you’re ready for the next sight, head to Duomo Di Milano Museum. From there, take a leisurely stroll to Chiesa Di Santa Maria Presso San Satiro, another of the city’s underrated attractions.

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.

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.

Treat yourself to a delightful dinner at Hotel Morfeo Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Contraste? It's another excellent option with a diverse menu. Consider reserving a table at UNAHOTELS Galles Milano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Nottingham Forest, a well-loved spot among locals and tourists. Or, head to Armani/bamboo Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Mag Cafe, another top-rated place 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 in Italy.

Day 8 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Don’t miss Navigli in Milan today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Milan is home to plenty of attractions that offer fun adventures, picturesque spots, and historic treasures! Start at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a popular museum that is worthwhile a visit in the city. Nearby, you’ll find Sforzesco Castle Art Library, enchanting visitors with its picture-perfect appeal. Continue your exploration at Pinacoteca Di Brera. This art gallery is one of the city’s most notable spots.

Enjoy the freedom of exploring Milan at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Saint Mary Assunta Cathedral.

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 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 delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After your meal, keep the night alive at a bar like Kilburn Cocktail Bar Milano, known for its lively atmosphere. Bar Frida is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, The Friends Pub Milano offers an excellent atmosphere for those looking to amp up the evening.

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

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Bologna. You’ll stay here for 1 night.

Prepare for a day full of family-friendly attractions, picturesque spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Pinacoteca Nazionale Di Bologna. This worthwhile art gallery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Two Towers, one of the city’s best highlights.

Next, check out Bologna Cathedral, one of the most curiosity-inducing places to see in Milan. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Palazzo Re Enzo. Wander around and soak in the respected atmosphere this palace offers. Then, head to Biblioteca Comunale Dell'archiginnasio, a top-rated library that adds another dimension to your day. Finally, visit the widely recognized Piazza Maggiore, the last of our attraction recommendations for today.

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

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

Unwind after your meal by stepping into Bar Al Bricco D'oro. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Freud E Squisito offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Osteria Del Sole, another top-rated bar in the area.

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

On day 10 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.

Bologna is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Ponte Vecchio, a globally renowned historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its picture-perfect appeal. Continue your exploration at Basilica Of Santa Croce In Florence. This church is one of the city’s most captivating spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Palazzo Vecchio. After exploring the palace, head to the extraordinary Piazza Della Signoria. This public square will wrap up today’s self-guided sightseeing tour in the city.

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

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

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Greet day 11 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 2 nights 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 Florence and San Gimignano.

Start your day at Central Market. This picture-perfect food market is a popular place to see in Florence. Then, wander over to Cathedral Of Santa Maria Del Fiore. If grand sites excite you, this church will be right up your alley. Nearby, you’ll also find Galleria Dell'accademia. This detailed art gallery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, David is a notable spot in the city that will captivate you with its unique charm. When you’re done at the statue, don’t forget to check out the romantic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this famous observation deck in Florence.

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

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 and reflect on the day's adventures.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

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

On day 12 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.

Savor the day by visiting some of the best places to see in Florence, including a public square, a cemetery, a church, a monument, a palace and much more! Start your adventure at Piazza Del Duomo, Pisa. This iconic public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Campo Santo located in Florence for an enchanting atmosphere.

Next, immerse yourself in the setting of Pisa Cathedral. Its UNESCO world heritage-listed features will captivate you. After the church, continue your tour of the city with a visit to Leaning Tower Of Pisa. This monument has a breathtaking appeal. For a change of pace, head to Knights' Square. As one of the most underrated attractions in Florence, this public square is an excellent place to end your self-guided tour.

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

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.

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

Following your dinner, dive into the local bar culture at Gosh*. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Antico Caffè Del Moro - Art Bar Firenze, the perfect place for those looking to experience the best of the nightlife. Similarly, Quelo Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Experience an unparalleled adventure on day 13 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Fortezza Medicea (siena). This often recommended monument provides an insightful glimpse into the city's identity. Next, discover Basilica Of San Domenico, a stunning church, promising a delightful encounter.

Continue your sightseeing with a visit to Siena Cathedral, a notable church. When you’re done, don’t forget to make a stop at the frequently visited Porta Tufi. Round off your day at Pubblico Palace, another gem in Florence 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 Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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.

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 14 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 San Gimignano. In the evening, you’ll end up in Trieste, where you will stay for 1 night.

Today’s itinerary in Siena covers several incredible sights, including a monument, a public square, a castle, a park and much more! Start your adventure at Porta San Giovanni. This underrated monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Piazza Del Duomo, a must-see public square in the village.

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 Rocca Di Montestaffoli. This increasingly popular castle offers an enriching experience. For a change of pace, head to Parco Della Rocca, where you can take in romantic features.

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

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

Enjoy a lovely meal at Caffè degli Specchi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Istriano Of Giobi And Oxa is another top choice with a popular menu. You could also check for a table at Chimera di Bacco. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Trieste tonight.

Let the evening flow smoothly from dinner to drinks at "life" New Bar Torinese Snc, a top-rated bar in the area. For other recommendations, White Cafe provides a perfect setting for rounding out your night with style and great drinks. Likewise, Café James Joyce offers a memorable night with diverse drink options and excellent service.

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