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!

Today’s itinerary in Trieste covers several incredible sights, including a castle, a street, a public square, a museum, a church and much more! Start your adventure at Miramare Castle. This notable castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Canale Ponterosso Trieste, a must-see street 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 Piazza Della Borsa. This intriguing public square offers an enriching experience. For a change of pace, head to Piazza Unità D'italia, where you can take in stunning features. Conclude your self-guided sightseeing tour with a visit to Revoltella Museum and Cattedrale Di San Giusto Martire. These sights offer a fulfilling end to a perfect day.

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

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

Enjoy a lovely dining experience at Rustiko, a popular restaurant in Trieste. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Trieste at Caffè San Marco, 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 Osteria Marise. It’s yet another ideal choice to enhance your time in Trieste tonight.

Keep the excitement of the evening going by visiting a bar or two. Mast is an excellent place to start. You could also check out Urbanis, offering a different kind of charm. A last recommendation for the day is Coktail Bar Trieste | La Preferita. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 3 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Venice. In the evening, you’ll end up in Venice, where you will stay for 2 nights.

Immerse yourself in Trieste’s rich culture with today's sightseeing itinerary. Start your journey at Bridge Of Sighs. This romantic monument is sure to ignite your curiosity. Next, dive into the romantic features of Doge's Palace, a must-visit palace 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 St Mark's Basilica, a notable church. For a change of scene, check out Piazza San Marco, known for its enchanting features. We also recommend visiting Grand Canal. This street is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Rialto Bridge, yet another iconic attraction in Trieste.

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

Don’t miss out on dining at Bauer Hotel, a top-rated dining destination in Venice. If you're in the mood to try something new, consider L'Osteria Le Guglie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Al Parlamento stands out as an excellent choice for a post-dinner cocktail. Alternatively, The Caffe Rosso offers an ideal atmosphere to enjoy the pleasures of the night. Adagio is also a great option that provides a perfect setting for a relaxing evening.

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

At the end of the day, you'll drive back to Venice, where you'll stay for 1 night more.

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

Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most up-and-coming attractions included on the itinerary is Murano. This romantic handicraft store will help you start your sightseeing on top. Then, take a leisurely stroll to Santa Maria Gloriosa Dei Frari and learn what makes this breathtaking church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the curiosity-inducing Gallerie Dell'accademia. After exploring the art gallery, head to Peggy Guggenheim Collection. This well-known art gallery is a highlight in Venice. As your day continues, stop by Santa Maria Della Salute, known for its history-steeped features.

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

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 delightful dinner at Generator Venice, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Nevodi? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante La Piazza as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

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

On day 5 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 2 nights.

Get ready to discover some of the most iconic wonders in Venice, including a botanical garden, a historical landmark, a public square, a stadium, a museum and much more! Start your day at Giusti Garden. This eye-catching botanical garden is a curiosity-inducing place to see in Venice. Then, wander over to Ponte Pietra. If history-steeped sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Piazza Delle Erbe. This stunning public square is a favorite among visitors.

Venice offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Verona Arena is a world-famous spot in the city that will captivate you with its unique charm. When you’re done at the stadium, don’t forget to check out the remarkable Fontana Di Piazza Bra. Take a moment to appreciate the fascinating details of this up-and-coming public square. Wrap up your self-guided tour of Venice's top attractions with a visit to Castelvecchio Museum.

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.

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 excitement of the evening going by visiting a bar or two. Archivio is an excellent place to start. You could also check out La Segreteria Café, offering a different kind of charm. A last recommendation for the day is Grande Giove Cocktail Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Verona 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 Sirmione, Desenzano Del Garda, Peschiera del Garda, Pacengo, and Moniga del Garda.

Verona is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Archaeological Site Of Grotte Di Catullo, a well-known archeological site that is worthwhile a visit in the town. Nearby, you’ll find Scaliger Castle, enchanting visitors with its history-steeped appeal. Continue your exploration at Castello Di Desenzano Del Garda. This castle is one of the town’s most up-and-coming spots.

Enjoy the freedom of exploring Verona at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Porta Brescia. After exploring the historical landmark, head to the locally appreciated Escape From Atlantis. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Spiaggia Porto, a place of romantic interest in Verona.

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

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

Enjoy a delicious meal at Trattoria I Masenini, a highly-rated dining destination in Verona. If you're eager to try something different, consider Osteria da Ugo, another top spot with a tantalizing menu. You might also want to secure a reservation at Locanda 4 Cuochi. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Verona this evening.

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

Raise your glass to another unforgettable day 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.

Bring your curiosity for today’s adventure around Verona. Some of the city’s most loved attractions await! La Scala is the perfect place to start. This opera house is one of the most well-known places to visit in Verona. Next, head to Galleria Vittorio Emanuele Ii, a spectacular shopping mall, known for its detailed 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 Duomo Di Milano Museum. This history-steeped church is a highly recommended experience. Nearby, you'll also find Chiesa Di Santa Maria Presso San Satiro. Visit these for an interesting touch 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 Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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.

Enjoy a delicious meal at Hotel Morfeo Milano, a highly-rated dining destination in Milan. If you're eager to try something different, consider Contraste, another top spot with a tantalizing menu. You might also want to secure a reservation at UNAHOTELS Galles Milano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Nottingham Forest, known for its inviting atmosphere. Armani/bamboo Bar is another great option if you’re looking for a place to get the night started. Similarly, Mag Cafe provides a great setting to enjoy the night away.

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

On day 8 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 1 night and discover all the best things to see and do in the area.

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.

Start by visiting Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a prime spot to begin your journey. This standout museum is sure to impress. Next on your list is Sforzesco Castle Art Library, another must-visit landmark and astonishing castle renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to Pinacoteca Di Brera. This history-steeped art gallery is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Saint Mary Assunta Cathedral, a popular church.

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

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.

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

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

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

A blend of family-friendly attractions, photo-friendly spots, and historic treasures await you in Milan on today’s itinerary. First up is the underrated art gallery, Pinacoteca Nazionale Di Bologna. Afterward, continue to Two Towers, a monument 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 Bologna Cathedral. This worthwhile church is an essential stop. Following that, head to Palazzo Re Enzo, another must-visit site that will enhance your experience. Don’t forget to stop by Biblioteca Comunale Dell'archiginnasio, an up-and-coming library in the city. Finally, end your day with a visit to Piazza Maggiore, a visually striking public square that offers the perfect conclusion to your sightseeing of the day.

At the end of the day, you will drive to Bologna, 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 Bologna's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at Ristorante Ciacco, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Ballarini boasts a menu that's sure to impress. Also, be sure to check out Sfoglia Rina. Known as a local hotspot, it’s a great choice for tonight in Bologna.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, another top-rated place in the area.

Raise your glass to another unforgettable day in Italy!

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Florence, 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 3 nights.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the globally renowned Ponte Vecchio, an enchanting historical landmark in Bologna. Next, go to Uffizi Gallery.

After visiting Ponte Vecchio and Uffizi Gallery, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of Santa Croce In Florence. This heritage-rich church 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 Piazza Della Signoria, one of the most culturally significant places to visit in Bologna.

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

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

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 your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!

Wake up to day 11 of your extraordinary road trip in Italy. With 2 nights left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Central Market. This visually striking food market is sure to ignite your curiosity. Next, dive into the romantic 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, an interesting art gallery. We also recommend visiting Piazzale Michelangelo. This observation deck is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Sangimignano1300, yet another intriguing attraction in Florence.

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

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

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazza Del Duomo, Pisa is the perfect place to start. This public square is one of the most wondrous places to visit in Florence. Next, head to Campo Santo, an up-and-coming cemetery, known for its historic 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 Pisa Cathedral. This picture-perfect church is a highly recommended experience. Nearby, you'll also find Leaning Tower Of Pisa and Knights' Square. Visit these for an interesting touch to your journey. Finish the day with a visit to Palazzo Gambacorti, a visually striking palace in Florence.

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

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

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

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.

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

On day 13 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.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Fortezza Medicea (siena), a frequently visited monument in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this breathtaking church.

There are many interesting places to see in Florence, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most captivating inviting spots of interest. After exploring the church, visit the up-and-coming Porta Tufi. Not far away, you'll also find Pubblico Palace. This palace is a historic highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazza Del Campo, a widely recognized public square in the city.

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.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 14 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Trieste, where you’ll be staying 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 often recommended monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant 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 curiosity-inducing castle offers an enriching experience. For a change of pace, head to Parco Della Rocca, where you can take in romantic features. These sights offer a fulfilling end to a perfect day.

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

Savor the flavors at Caffè degli Specchi, a top pick for dinner tonight. Alternatively, Osteria Istriano Of Giobi And Oxa beckons with its unique menu offerings. Also, consider Chimera di Bacco. With its consistent customer satisfaction, it’s an excellent option for dining in Trieste tonight.

Unwind after your meal by stepping into "life" New Bar Torinese Snc. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, White Cafe offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Café James Joyce, another top-rated bar in the area.

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