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

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

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Trieste on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Miramare Castle is the first of them. Spend some time admiring this enchanting castle before continuing your journey. Canale Ponterosso Trieste is your next stop. This locally appreciated street is one of the best-rated sights in Trieste.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Della Borsa. This standout public square is a sight to behold. To round off your sightseeing experience, visit Piazza Unità D'italia and Revoltella Museum. If time allows, end your day with Cattedrale Di San Giusto Martire, a historic church that offers a memorable conclusion to your exploration.

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 and reflect on the day'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.

Continue the enjoyment post-dinner at Mast, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Urbanis offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Coktail Bar Trieste | La Preferita. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Venice, 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 Venice. You’ll stay here for 2 nights.

Trieste is brimming with adventures. Today’s wonderful stops include a monument, a palace, a church, a public square, a street, a historical landmark and much more! Begin your sightseeing adventure at the notable Bridge Of Sighs and allow yourself time to explore. Just a short distance away you'll find your next stop, Doge's Palace, a culturally significant palace that draws visitors from far and near.

Continue your journey to St Mark's Basilica, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the timeless Piazza San Marco. When you're finished at the public square, Grand Canal awaits your visit. This street is a history-steeped highlight on today's itinerary. Last up is a historical landmark - the globally renowned Rialto Bridge.

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.

Have a fantastic dining experience at Bauer Hotel, a highly recommended choice for tonight's dinner. If you're looking to mix things up, L'Osteria Le Guglie offers an enticing alternative with its varied menu. Additionally, Corner Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

After your meal, keep the night alive at a bar like Al Parlamento, known for its lively atmosphere. The Caffe Rosso is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Adagio offers an excellent atmosphere for those looking to amp up the evening.

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

Greet day 4 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Venice 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 Murano and Venice.

One of the most iconic places you can visit today in Murano is Cannaregio. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Venice. Begin your sightseeing with Murano. This often recommended handicraft store is one of the top attractions in the village. Proceed to Santa Maria Gloriosa Dei Frari, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Gallerie Dell'accademia. This locally appreciated art gallery is a traveler-favorite. Not far away, you’ll find Peggy Guggenheim Collection, another key site on your sightseeing itinerary. Santa Maria Della Salute is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Il Mercante, known for its inviting atmosphere. The Irish Pub Venezia is another great option if you’re looking for a place to get the night started. Similarly, Ai Stagneri provides a great setting to enjoy the night away.

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

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and natural wonders. Whether you decide to explore Venice on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Giusti Garden is the first of them. Spend some time admiring this eye-catching botanical garden before continuing your journey. Ponte Pietra is your next stop. This captivating historical landmark is one of the best-rated sights in Venice.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Delle Erbe. This history-steeped public square is a sight to behold. To round off your sightseeing experience, visit Verona Arena and Fontana Di Piazza Bra. If time allows, end your day with Castelvecchio Museum, a history-steeped museum that offers a memorable conclusion to your exploration.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Verona. Verona 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 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.

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

Raise your glass to another unforgettable day in Italy!

On day 6 of your road trip, you’ll start and end your day in Verona, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Sirmione, Desenzano Del Garda, Peschiera del Garda, Pacengo, and Moniga del Garda. You still have 1 night left in Verona.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the locally renowned Archaeological Site Of Grotte Di Catullo, a visually striking archeological site in Verona. Next, go to Scaliger Castle.

After visiting Archaeological Site Of Grotte Di Catullo and Scaliger Castle, have a stroll along Verona's streets and take in the local charm. Continue your sightseeing by heading to Castello Di Desenzano Del Garda. This standout castle offers a unique experience. Porta Brescia is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Escape From Atlantis, one of the most breathtaking places to visit in Verona. If you still have some time left for sightseeing, we also recommend stopping by Spiaggia Porto.

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.

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 enjoying a fulfilling meal, continue your evening at Duchi Café, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Cambridge Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Rubicone Caffe provides an excellent environment for a relaxed and enjoyable evening.

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

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.

Today, you'll explore some of the most beautiful places in Verona, including an opera house, a shopping mall, and a church. Start your day with a visit to La Scala. This interesting opera house is a must-visit in the city. When you’re ready for your next discovery, continue to Galleria Vittorio Emanuele Ii, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Verona 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 Duomo Di Milano Museum, a timeless church in the city. If you’re up for more discoveries, don’t forget to reserve some time for 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 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.

Enjoy a lovely meal at Hotel Morfeo Milano, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Contraste is another top choice with a popular menu. You could also check for a table at UNAHOTELS Galles Milano. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

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.

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

Day 8 offers a multitude of experiences. You will stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

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.

Get ready to discover some of the most iconic wonders in Milan, including a museum, a castle, an art gallery, a church and much more! Start your day at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This eye-catching museum is a notable place to see in Milan. Then, wander over to Sforzesco Castle Art Library. If picture-perfect sites excite you, this castle will be right up your alley. Nearby, you’ll also find Pinacoteca Di Brera. This standout art gallery 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, Saint Mary Assunta Cathedral is a captivating spot in the city that will captivate you with its unique charm.

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.

Enjoy a lovely dining experience at Dessert Bar Milano, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Radisson Blu Hotel Milan, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Ristorante Qui Si Mangia. It’s yet another ideal choice to enhance your time in Milan tonight.

Round off your dining experience by visiting Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.

Say good night to Milan and look forward to another great day of your road trip 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, picturesque spots, and historic treasures await you in Milan on today’s itinerary. First up is the intriguing 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 often recommended 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 often recommended library in the city. Finally, end your day with a visit to Piazza Maggiore, a romantic public square that offers the perfect conclusion to your sightseeing of the day.

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.

Savor the flavors at Ristorante Ciacco, a top pick for dinner tonight. Alternatively, Ristorante Ballarini beckons with its unique menu offerings. Also, consider Sfoglia Rina. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

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.

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

On day 10 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Florence. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Bologna is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Ponte Vecchio, a wondrous historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its romantic appeal. Continue your exploration at Basilica Of Santa Croce In Florence. This church is one of the city’s most notable 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 top-rated Piazza Della Signoria.

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.

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.

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

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, 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!

On day 11 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 2 nights more, there’s no need to rush. Experience Florence and San Gimignano to the fullest today with this curated day itinerary!

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Central Market. This instagrammable food market is sure to ignite your curiosity. Next, dive into the history-steeped 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 well-known 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 increasingly popular attraction in Florence.

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

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

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 12 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Get ready for a day filled with family-friendly attractions, breathtaking views, and photo-friendly spots in the charming city of Florence. Your adventure starts at Piazza Del Duomo, Pisa, a timeless local hot spot. Another notable attraction to explore is Campo Santo. This beloved cemetery is known for its historic appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Pisa Cathedral. This breathtaking church offers a fascinating experience that many visitors find memorable. Leaning Tower Of Pisa is also worth visiting, along with Knights' Square. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Palazzo Gambacorti. This increasingly popular palace provides a fitting finale to your sightseeing.

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

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.

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.

After your meal, keep the night alive at a bar like Gosh*, known for its lively atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Quelo Bar offers an excellent atmosphere for those looking to amp up the evening.

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

Dive into day 13 of your remarkable road trip in Italy. Today you will explore Siena, 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 Siena. You’ll stay here for 1 night.

Today’s agenda in Florence includes a monument, a church, a historical landmark, a palace, a public square and much more! Fortezza Medicea (siena) is must-visit monument and a great starting point for the day. Next, continue your journey to Basilica Of San Domenico, a locally appreciated church, located just a leisurely stroll away. Next, head to Siena Cathedral, a romantic church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the curiosity-inducing Porta Tufi. If you’re looking for more, Pubblico Palace is also an up-and-coming attraction that is worthwhile a visit. Lastly, don’t miss Piazza Del Campo, a place of romantic interest in the city.

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.

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 highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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 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.

Savor the day by visiting some of the best places to see in Siena, including a monument, a public square, a castle, a park and much more! Start your adventure at Porta San Giovanni. This curiosity-inducing monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Duomo located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Rocca Di Montestaffoli. Its romantic features will captivate you. After the castle, continue your tour of the village with a visit to Parco Della Rocca. Visitors usually appreciate the history-steeped features of this park.

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.

Make sure to reserve a table at Caffè degli Specchi, an iconic dining spot in Trieste. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Istriano Of Giobi And Oxa, a popular restaurant in Trieste. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Chimera di Bacco, a hidden gem nestled in Trieste. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to "life" New Bar Torinese Snc, ideal for a leisurely evening with a drink in hand. White Cafe is another bar that offers an enjoyable setting. Similarly, Café James Joyce is also a popular place to go on a night out, perfect for relaxing and socializing.

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