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 still have 1 night to spend in Trieste, there’s no need to rush. Experience Miramare / Miramar and Trieste to the fullest today with this curated day itinerary.

Miramare / Miramar is brimming with adventures.

Miramare Castle is perfect for a self-paced visit during the day. This standout castle is sure to impress. Next on your list is Canale Ponterosso Trieste, another must-visit landmark and frequently visited street renowned for its enchanting features.

While exploring and sightseeing, take time to savor the culture of Trieste by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Della Borsa. This picture-perfect public square is an essential place to visit for anyone looking for the full Trieste experience. We also recommend visiting Piazza Unità D'italia, a locally renowned public square. Nearby, you'll also find Revoltella Museum, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Cattedrale Di San Giusto Martire and wrap up your day with its stunning appeal.

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

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

Dine in style at Rustiko, a top recommendation for dinner tonight. Or, for a change of pace, Caffè San Marco boasts a menu that's sure to impress. Also, be sure to check out Osteria Marise. Known as a local hotspot, it’s a great choice for tonight in Trieste.

After enjoying a fulfilling meal, continue your evening at Mast, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Urbanis offers a welcoming atmosphere for easing into the nightlife. Similarly, Coktail Bar Trieste | La Preferita provides an excellent environment for a relaxed and enjoyable evening.

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

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of Venice. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 2 nights.

Enjoy all that Bridge Of Sighs has to offer. This is a well-known monument you should not miss. Another must-see is Doge's Palace, a well-known palace in Trieste.

When you’re ready for the next sight, head to St Mark's Basilica. From there, take a leisurely stroll to Piazza San Marco, another of the city’s globally renowned attractions. We recommend continuing your self-guided tour at Grand Canal, a visually striking place of interest in the city. If time allows, add Rialto Bridge to your itinerary. This timeless historical landmark offers the perfect finishing touch to your day in Trieste.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Venice. Venice 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 Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

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 recharge in preparation for another adventurous day in Italy!

On day 4 of your road trip, you’ll start and end your day in Venice, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Murano and Venice.

A visit to Cannaregio 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.

Murano is an ideal stop early in the day. This curiosity-inducing handicraft store is a must-visit in the village. When you’re ready for your next discovery, continue to Santa Maria Gloriosa Dei Frari, which may be one of the most monumental places you will experience today.

One of the best things about exploring Venice 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 Gallerie Dell'accademia, a curiosity-inducing art gallery in the village. If you’re up for more discoveries, don’t forget to reserve some time for Peggy Guggenheim Collection and Santa Maria Della Salute.

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

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

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

After your meal, keep the night alive at a bar like Il Mercante, known for its lively atmosphere. The Irish Pub Venezia is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ai Stagneri offers an excellent atmosphere for those looking to amp up the evening.

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

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

Make a stop at Giusti Garden. This increasingly popular botanical garden is a must-visit for travelers looking for a unique holiday experience. Make your way to Ponte Pietra located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Piazza Delle Erbe. Its stunning features will captivate you. After the public square, continue your tour of the city with a visit to Verona Arena. Visitors usually appreciate the enchanting features of this stadium. Next up is Fontana Di Piazza Bra, a highly recommended public square. For a change of pace, head to Castelvecchio Museum. As one of the most captivating attractions in Venice, this museum is the perfect place to end your self-guided sightseeing tour.

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

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

Savor the flavors at La Griglia, a top pick for dinner tonight. Alternatively, Vecio Macello beckons with its unique menu offerings. Also, consider Via Fama Cafè | Verona. With its consistent customer satisfaction, it’s an excellent option for dining in Verona tonight.

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

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

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Sirmione, Desenzano Del Garda, Peschiera del Garda, Pacengo, and Moniga del Garda. With 1 night to stay in Verona, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Archaeological Site Of Grotte Di Catullo brings Verona's character to life. This romantic archeological site is a highlight of any visit in the town. Then, enjoy Scaliger Castle, another visually striking attraction that never fails to captivate visitors. Next, head over to Castello Di Desenzano Del Garda, one of the town’s most intriguing attractions, known for its awe-inspiring features.

If you’re looking for more, spend time soaking in the atmosphere of Porta Brescia. This breathtaking historical landmark is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Escape From Atlantis, a locally appreciated amusement park, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Spiaggia Porto before you head back to your hotel.

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

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

Savor the flavors at Trattoria I Masenini, a top pick for dinner tonight. Alternatively, Osteria da Ugo beckons with its unique menu offerings. Also, consider Locanda 4 Cuochi. With its consistent customer satisfaction, it’s an excellent option for dining in Verona tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Duchi Café, known for its inviting atmosphere. Cambridge Bar is another great option if you’re looking for a place to get the night started. Similarly, Rubicone Caffe provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Milan are on today's agenda. In the evening, you’ll end up in Milan, where you will stay for 2 nights.

Whatever your travel style is, La Scala is an essential stop in Verona. This well-known opera house provides an insightful glimpse into the city's identity. Next, discover Galleria Vittorio Emanuele Ii, a romantic shopping mall, promising a delightful encounter.

Continue your sightseeing with a visit to Duomo Di Milano Museum, a timeless church. When you’re done, don’t forget to make a stop at the frequently visited Chiesa Di Santa Maria Presso San Satiro.

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.

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

Don’t miss out on dining at Hotel Morfeo Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Contraste, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Galles Milano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

After savoring a delicious meal, step into the vibrant nightlife at Nottingham Forest, where the evening is just getting started. In the same way, Armani/bamboo Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Mag Cafe is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 8 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Milan.

A top thing to do today is to explore Navigli, a must-see neighborhood in Milan. It's the perfect starting point for touring the top attractions in the area.

No visit to Milan is complete without Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This notable museum is one of the top attractions in the city. Proceed to Sforzesco Castle Art Library, 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 Pinacoteca Di Brera. This interesting art gallery is a traveler-favorite. Not far away, you’ll find Saint Mary Assunta Cathedral, another key site on your sightseeing itinerary.

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

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

Have a fantastic dining experience at Dessert Bar Milano, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Radisson Blu Hotel Milan offers an enticing alternative with its varied menu. Additionally, Ristorante Qui Si Mangia is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

Savor another day of unforgettable experiences in Italy!

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Bologna, where you’ll be staying for 1 night.

Start your day at Pinacoteca Nazionale Di Bologna. This eye-catching art gallery is an intriguing place to see in Milan. Then, wander over to Two Towers. If stunning sites excite you, this monument will be right up your alley. Nearby, you’ll also find Bologna Cathedral. This breathtaking church is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Palazzo Re Enzo is a curiosity-inducing spot in the city that will captivate you with its unique charm. When you’re done at the palace, don’t forget to check out the instagrammable Biblioteca Comunale Dell'archiginnasio. Take a moment to appreciate the fascinating details of this worthwhile library. Wrap up your self-guided tour of Milan's top attractions with a visit to Piazza Maggiore.

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

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

Make sure to reserve a table at Ristorante Ciacco, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Ballarini, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sfoglia Rina, a hidden gem nestled in Bologna. 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 Bar Al Bricco D'oro, known for its lively atmosphere. Bar Freud E Squisito is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Osteria Del Sole offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 3 nights.

Experience Ponte Vecchio, a wondrous historical landmark in the city. Then, head to Uffizi Gallery and soak in the ambiance of this historic art gallery.

There are many interesting places to see in Bologna, and when you are ready for more, go to Basilica Of Santa Croce In Florence. This is one of the city’s most interesting respected spots of interest. After exploring the church, visit the popular Palazzo Vecchio. Not far away, you'll also find Piazza Della Signoria. This public square is a majestic highlight in Bologna.

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

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

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass and celebrate another amazing 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 have 2 nights to stay in Florence, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Florence and San Gimignano.

Check out the locally renowned food market, Central Market. Afterward, continue to Cathedral Of Santa Maria Del Fiore, a church every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Galleria Dell'accademia. This notable art gallery is an essential stop. Following that, head to David, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, an impressive observation deck in the city. Finally, end your day with a visit to Sangimignano1300, a historic museum that offers the perfect conclusion to your sightseeing of the day.

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

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

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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Savor another day of unforgettable experiences in Italy!

On day 12 of your road trip, you'll get the chance to experience Pisa. At the end of the day, you'll drive back to Florence, where you still have 1 night left to stay.

Start your day at Piazza Del Duomo, Pisa. This stunning public square is a wondrous place to see in Florence. Then, wander over to Campo Santo. If historic sites excite you, this cemetery will be right up your alley. Nearby, you’ll also find Pisa Cathedral. This breathtaking church 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, Leaning Tower Of Pisa is an iconic spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the standout Knights' Square. Take a moment to appreciate the fascinating details of this intriguing public square. Wrap up your self-guided tour of Florence's top attractions with a visit to Palazzo Gambacorti.

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

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.

Enjoy a delicious meal 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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.

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

Your itinerary for day 13 of your road trip in Italy includes 1 stop and features some of the highlights of Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 1 night.

One of the most curiosity-inducing attractions included on the itinerary is Fortezza Medicea (siena). This culturally significant monument will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica Of San Domenico and learn what makes this breathtaking church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the well-known Siena Cathedral. After exploring the church, head to Porta Tufi. This beloved historical landmark is a highlight in Florence. As your day continues, stop by Pubblico Palace, known for its breathtaking features. Lastly, don’t forget to check out the impressive Piazza Del Campo. Enjoy exploring this incredible public square at your own pace.

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

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

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

Dive into day 14 of your remarkable road trip in Italy. Today you'll explore 1 destination, including San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in Trieste, where you'll spend 1 night.

Porta San Giovanni brings Siena's character to life. This historic monument is a highlight of any visit in the village. Then, enjoy Piazza Del Duomo, another symbolic attraction that never fails to captivate visitors. Next, head over to Rocca Di Montestaffoli, one of the village’s most curiosity-inducing attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Parco Della Rocca. This enchanting park is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Trieste. Trieste 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 Trieste. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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 consistently gains high praises from customers, it’s an ideal choice in Trieste tonight.

Keep the evening going at "life" New Bar Torinese Snc, a great choice for enjoying the after-dinner hours with a drink. You could also go to White Cafe, which offers a similarly pleasant setting and great drinks. Another option is Café James Joyce, which provides an inviting environment for unwinding after a busy day out.

Head back to your accommodation in Trieste and get some rest to prepare for another magical day of your road trip in Italy.