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

Greet day 2 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Trieste 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 Miramare / Miramar and Trieste.

Trieste is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Miramare Castle, a well-known castle that is worthwhile a visit in the village. Nearby, you’ll find Canale Ponterosso Trieste, enchanting visitors with its awe-inspiring appeal. Continue your exploration at Piazza Della Borsa. This public square is one of the village’s most frequently visited spots.

Enjoy the freedom of exploring Trieste at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Unità D'italia. After exploring the public square, head to the up-and-coming Revoltella Museum. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Cattedrale Di San Giusto Martire, a place of historic interest in Trieste.

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.

Savor the flavors at Rustiko, a top pick for dinner tonight. Alternatively, Caffè San Marco beckons with its unique menu offerings. Also, consider Osteria Marise. With its consistent customer satisfaction, it’s an excellent option for dining in Trieste tonight.

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.

Savor another day of unforgettable experiences 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.

Savor the day by visiting some of the best places to see in Trieste, including a monument, a palace, a church, a public square, a street, a historical landmark and much more! Start your adventure at Bridge Of Sighs. This notable monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Doge's Palace located in Trieste for another exciting encounter.

Next, immerse yourself in the setting of St Mark's Basilica. Its visually striking features will captivate you. After the church, continue your tour of the city with a visit to Piazza San Marco. Visitors usually appreciate the enchanting features of this public square. Next up is Grand Canal, a highly recommended street. For a change of pace, head to Rialto Bridge. As one of the most iconic attractions in Trieste, this historical landmark is the perfect place to end your self-guided sightseeing tour.

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.

Savor the flavors at Bauer Hotel, a top pick for dinner tonight. Alternatively, L'Osteria Le Guglie beckons with its unique menu offerings. Also, consider Corner Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

Keep the evening going at Al Parlamento, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Caffe Rosso, which offers a similarly pleasant setting and great drinks. Another option is Adagio, which provides an inviting environment for unwinding after a busy day out.

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

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

Set aside time today to explore Cannaregio, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. 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. Murano is the first of them. Spend some time admiring this enchanting handicraft store before continuing your journey. Santa Maria Gloriosa Dei Frari is your next stop. This underrated church 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 Gallerie Dell'accademia. This visually striking art gallery is a sight to behold. To round off your sightseeing experience, visit Peggy Guggenheim Collection and Santa Maria Della Salute.

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

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.

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

Brace yourself for today’s incredible lineup of attractions in Venice, featuring fun adventures, romantic experiences, and natural wonders. Start at Giusti Garden, an up-and-coming botanical garden in the city. Then, head to Ponte Pietra and soak in the ambiance of this visually striking historical landmark.

There are many interesting places to see in Venice, and when you are ready for more, go to Piazza Delle Erbe. This is one of the city’s most well-known romantic spots of interest. After exploring the public square, visit the timeless Verona Arena. Not far away, you'll also find Fontana Di Piazza Bra. This public square is a history-steeped highlight in Venice. Before wrapping up your self-guided sightseeing tour, head to Castelvecchio Museum, a well-known museum 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 Verona. Verona 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 Verona. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Don’t miss out on dining at La Griglia, a top-rated dining destination in Verona. If you're in the mood to try something new, consider Vecio Macello, another top spot with a mouthwatering menu. You might also want to secure a reservation at Via Fama Cafè | Verona. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Verona this evening.

After savoring a delicious meal, step into the vibrant nightlife at Archivio, where the evening is just getting started. In the same way, La Segreteria Café offers a unique charm perfect for experiencing the local bar scene in Verona. Grande Giove Cocktail Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Savor another day of unforgettable experiences in Italy!

On day 6 of your road trip in Italy, you’ll start and end your day in Verona, but spend the day exploring what’s beyond the city. Since you will return to Verona for 1 night more, there’s no need to rush. Experience Sirmione, Desenzano Del Garda, Peschiera del Garda, Pacengo, and Moniga del Garda to the fullest today with this curated day itinerary!

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in Verona. Begin your sightseeing with Archaeological Site Of Grotte Di Catullo. This notable archeological site is one of the top attractions in the town. Proceed to Scaliger Castle, another must-visit attraction.

As you wander through the inviting streets of Verona, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Castello Di Desenzano Del Garda. This up-and-coming castle is a traveler-favorite. Not far away, you’ll find Porta Brescia, another key site on your sightseeing itinerary. Escape From Atlantis is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Spiaggia Porto and uncover why it's recognized as one of the town's most locally appreciated attractions.

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

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.

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.

Explore the vibrant nightlife at Duchi Café after your meal, a hub for lively evenings and memorable moments. Or, head to Cambridge Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Rubicone Caffe is perfect for those looking to extend their night with a touch of local flavor.

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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Milan, 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 Milan. You’ll stay here for 2 nights.

Verona is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and photo-friendly spots! Start at La Scala, an interesting opera house that is worthwhile a visit in the city. Nearby, you’ll find Galleria Vittorio Emanuele Ii, enchanting visitors with its history-steeped appeal. Continue your exploration at Duomo Di Milano Museum. This church is one of the city’s most wondrous 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 Chiesa Di Santa Maria Presso San Satiro.

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

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

Enjoy a delicious meal 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.

Keep the excitement of the evening going by visiting a bar or two. Nottingham Forest is an excellent place to start. You could also check out Armani/bamboo Bar, offering a different kind of charm. A last recommendation for the day is Mag Cafe. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and recharge in preparation for another adventurous day 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 Milan by discovering the best things there are to see and do in the city.

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

Start by visiting Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a prime spot to begin your journey. This photogenic museum is sure to impress. Next on your list is Sforzesco Castle Art Library, another must-visit landmark and top-rated 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 respected 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 locally renowned 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.

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 delicious dinner at Dessert Bar Milano, an excellent option for tonight's dining. Looking for something different? Radisson Blu Hotel Milan offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Qui Si Mangia. With its reputation for pleasing customers, it’s a fantastic choice 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.

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

Embark on another extraordinary experience on day 9 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

Milan is brimming with adventures. Today’s wonderful stops include an art gallery, a monument, a church, a palace, a library, a public square and much more! Begin your sightseeing adventure at the beloved Pinacoteca Nazionale Di Bologna and allow yourself time to explore. Just a short distance away you'll find your next stop, Two Towers, a historic monument that draws visitors from far and near.

Continue your journey to Bologna Cathedral, one of the city’s most beloved spots that you shouldn’t miss. Another great site to visit is the up-and-coming Palazzo Re Enzo. When you're finished at the palace, Biblioteca Comunale Dell'archiginnasio awaits your visit. This library is an eye-catching highlight on today's itinerary. Last up is a public square - the top-rated Piazza Maggiore.

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.

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

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.

If you’re not ready to end the night just yet, Bar Al Bricco D'oro offers a perfect venue to relax and savor a drink. Similarly, Bar Freud E Squisito is well-suited for those looking to unwind in a social setting. Osteria Del Sole is another excellent spot to enjoy a nightcap after a delightful meal.

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

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Bologna. Your adventure starts at Ponte Vecchio, a world-famous local hot spot. Another notable attraction to explore is Uffizi Gallery. This astonishing art gallery is known for its romantic appeal.

After soaking in the highlights of these sights, take some time to wander Bologna's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Of Santa Croce In Florence. This heritage-rich church offers a fascinating experience that many visitors find memorable. Palazzo Vecchio is also worth visiting, along with Piazza Della Signoria. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

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

A blend of fun adventures, photo-friendly spots, and budget-friendly activities await you in Florence on today’s itinerary. First up is the captivating 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 locally renowned 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, a spectacular observation deck in the city. Finally, end your day with a visit to Sangimignano1300, an instagrammable 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.

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

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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

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.

Florence is brimming with adventures. Today’s wonderful stops include a public square, a cemetery, a church, a monument, a palace and much more! Begin your sightseeing adventure at the globally renowned Piazza Del Duomo, Pisa and allow yourself time to explore. Just a short distance away you'll find your next stop, Campo Santo, a breathtaking cemetery that draws visitors from far and near.

Continue your journey to Pisa Cathedral, one of the city’s most underrated spots that you shouldn’t miss. Another great site to visit is the globally renowned Leaning Tower Of Pisa. When you're finished at the monument, Knights' Square awaits your visit. This public square is a historic highlight on today's itinerary. Last up is a palace - the frequently visited Palazzo Gambacorti.

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 Ristorante Buca Mario, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Agricola Toscana is another top choice with a popular menu. You could also check for a table at Eataly Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Continue your evening by exploring the vibrant nightlife scene at Gosh*, a prime destination for a thrilling night out. Also, don’t forget to check out Antico Caffè Del Moro - Art Bar Firenze, a bar that offers unique local touches. Likewise, Quelo Bar provides an excellent alternative for a fun evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg 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.

Discover a day packed with family-friendly attractions, scenic views, and photo-friendly spots in Florence. Begin your sightseeing with Fortezza Medicea (siena). This locally appreciated monument is one of the top attractions in the city. Proceed to Basilica Of San Domenico, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Siena Cathedral. This locally renowned church is a traveler-favorite. Not far away, you’ll find Porta Tufi, another key site on your sightseeing itinerary. Pubblico Palace is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Campo and uncover why it's recognized as one of the city's most spectacular attractions.

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

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

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to another unforgettable 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.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a monument, a public square, a castle, a park and much more! Begin your adventure at Porta San Giovanni. This is an up-and-coming monument you should not miss. Another must-see is Piazza Del Duomo, a curiosity-inducing public square in Siena.

When you’re ready for the next sight, head to Rocca Di Montestaffoli. From there, take a leisurely stroll to Parco Della Rocca, another of the village’s often recommended attractions.

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.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, "life" New Bar Torinese Snc stands out as an excellent choice for a post-dinner cocktail. Alternatively, White Cafe offers an ideal atmosphere to enjoy the pleasures of the night. Café James Joyce 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!