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!

Get ready for an exciting day in Trieste. Today’s sightseeing agenda includes a castle, a street, a public square, a museum, a church and much more! Begin your adventure at Miramare Castle. This is an interesting castle you should not miss. Another must-see is Canale Ponterosso Trieste, an often recommended street in Trieste.

When you’re ready for the next sight, head to Piazza Della Borsa. From there, take a leisurely stroll to Piazza Unità D'italia, another of the village’s popular attractions. We recommend continuing your self-guided tour at Revoltella Museum, a history-steeped place of interest in the village. If time allows, add Cattedrale Di San Giusto Martire to your itinerary. This increasingly popular church offers the perfect finishing touch to your day in Trieste.

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

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.

Make sure to reserve a table at Rustiko, 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 Caffè San Marco, 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 Osteria Marise, a hidden gem nestled in Trieste. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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.

Today, you'll explore some of the most beautiful places in Trieste, including a monument, a palace, a church, a public square, a street, a historical landmark and much more! Start your day with a visit to Bridge Of Sighs. This popular monument is a must-visit in the city. When you’re ready for your next discovery, continue to Doge's Palace, which may be one of the most UNESCO world heritage-designated places you will experience today.

One of the best things about exploring Trieste 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 St Mark's Basilica, a notable church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza San Marco and Grand Canal. End your day with a visit to Rialto Bridge, a world-famous historical landmark that’s sure to leave a lasting impression.

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 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.

Dine in style at Bauer Hotel, a top recommendation for dinner tonight. Or, for a change of pace, L'Osteria Le Guglie boasts a menu that's sure to impress. Also, be sure to check out Corner Pub. Known as a local hotspot, it’s a great choice for tonight in Venice.

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

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

A visit to Cannaregio in Murano 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.

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming village of Venice. Your adventure starts at Murano, an often recommended local hot spot. Another notable attraction to explore is Santa Maria Gloriosa Dei Frari. This intriguing church is known for its visually striking appeal.

After soaking in the highlights of these sights, take some time to wander Venice's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Gallerie Dell'accademia. This instagrammable art gallery offers a fascinating experience that many visitors find memorable. Peggy Guggenheim Collection is also worth visiting, along with Santa Maria Della Salute. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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

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

Following your dinner, dive into the local bar culture at Il Mercante. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to The Irish Pub Venezia, the perfect place for those looking to experience the best of the nightlife. Similarly, Ai Stagneri provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Verona, 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 Verona. You’ll stay here 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 mesmerizing botanical garden is an often recommended place to see in Venice. Then, wander over to Ponte Pietra. If enchanting 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 wondrous 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 enchanting Fontana Di Piazza Bra. Take a moment to appreciate the fascinating details of this frequently visited public square. Wrap up your self-guided tour of Venice's top attractions with a visit to Castelvecchio Museum.

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.

Enjoy a lovely dining experience at La Griglia, a popular restaurant in Verona. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Verona at Vecio Macello, 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 Via Fama Cafè | Verona. It’s yet another ideal choice to enhance your time in Verona tonight.

Let the evening flow smoothly from dinner to drinks at Archivio, a top-rated bar in the area. For other recommendations, La Segreteria Café provides a perfect setting for rounding out your night with style and great drinks. Likewise, Grande Giove Cocktail Bar offers a memorable night with diverse drink options and excellent service.

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

On day 6 of your road trip, you’ll start and end your day in Verona, where you'll stay for 1 night more.

Savor the day by visiting some of the best places to see in Verona, including an archeological site, a castle, a historical landmark, an amusement park, a beach and much more! Start your adventure at Archaeological Site Of Grotte Di Catullo. This locally renowned archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Scaliger Castle located in Verona for another exciting encounter.

Next, immerse yourself in the setting of Castello Di Desenzano Del Garda. Its respected features will captivate you. After the castle, continue your tour of the town with a visit to Porta Brescia. Visitors usually appreciate the culturally significant features of this historical landmark. Next up is Escape From Atlantis, a highly recommended amusement park. For a change of pace, head to Spiaggia Porto. As one of the most often recommended attractions in Verona, this beach is the perfect place to end your self-guided sightseeing tour.

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

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.

Treat yourself to a delightful dinner at Trattoria I Masenini, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria da Ugo? It's another excellent option with a diverse menu. Consider reserving a table at Locanda 4 Cuochi as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Verona.

Unwind after your meal by stepping into Duchi Café. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Cambridge Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Rubicone Caffe, another top-rated bar in the area.

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

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Milan. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 2 nights here for some well-deserved relaxation.

Today’s agenda in Verona includes an opera house, a shopping mall, and a church. La Scala is must-visit opera house and a great starting point for the day. Next, continue your journey to Galleria Vittorio Emanuele Ii, a famous shopping mall, located just a leisurely stroll away. Next, head to Duomo Di Milano Museum, a symbolic church, also available for your discovery today.

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 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.

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.

Relax and recharge in preparation for another adventurous day 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.

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.

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

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

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

Cap off your dinner by heading to Kilburn Cocktail Bar Milano, ideal for a leisurely evening with a drink in hand. Bar Frida is another bar that offers an enjoyable setting. Similarly, The Friends Pub Milano 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!

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.

Brace yourself for today’s incredible lineup of attractions in Milan, featuring family-friendly attractions, picturesque spots, and history-rich sites. Start at Pinacoteca Nazionale Di Bologna, a curiosity-inducing art gallery in the city. Then, head to Two Towers and soak in the ambiance of this stunning monument.

There are many interesting places to see in Milan, and when you are ready for more, go to Bologna Cathedral. This is one of the city’s most up-and-coming monumental spots of interest. After exploring the church, visit the underrated Palazzo Re Enzo. Not far away, you'll also find Biblioteca Comunale Dell'archiginnasio. This library is a respected highlight in Milan. Before wrapping up your self-guided sightseeing tour, head to Piazza Maggiore, an impressive public square in the city.

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

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

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. 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.

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.

Today’s itinerary in Bologna covers several incredible sights, including a historical landmark, an art gallery, a church, a palace, a public square and much more! Start your adventure at Ponte Vecchio. This timeless historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Uffizi Gallery, a must-see art gallery in the city.

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 Basilica Of Santa Croce In Florence. This interesting church offers an enriching experience. For a change of pace, head to Palazzo Vecchio, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Piazza Della Signoria. These sights offer a fulfilling end to a perfect day.

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 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 Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice 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.

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

Greet day 11 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 2 nights in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Florence and San Gimignano.

Start your day with a visit to Central Market. This locally renowned food market is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Florence 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 Galleria Dell'accademia, an interesting art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for David and Piazzale Michelangelo. End your day with a visit to Sangimignano1300, a beloved museum that’s sure to leave a lasting impression.

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

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.

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.

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.

Savor another day of unforgettable experiences in Italy!

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

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Piazza Del Duomo, Pisa. This globally renowned public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Campo Santo, one of the city’s best highlights.

Next, check out Pisa Cathedral, one of the most intriguing places to see in Florence. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Leaning Tower Of Pisa. Wander around and soak in the historic atmosphere this monument offers. Then, head to Knights' Square, a top-rated public square that adds another dimension to your day. Finally, visit the beloved Palazzo Gambacorti, the last of our attraction recommendations for today.

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 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.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Head back to your accommodation in Florence and get some rest in preparation for another magical day 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.

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

Continue your sightseeing with a visit to Siena Cathedral, an interesting church. When you’re done, don’t forget to make a stop at the underrated Porta Tufi. Not far away from the historical landmark, you will find the UNESCO world heritage-listed Piazza Del Campo, perfect for a quick visit. Round off your day at Pubblico Palace, another gem in Florence with picture-perfect features to discover.

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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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

Dive into day 14 of your remarkable road trip in Italy. Today you will explore San Gimignano, 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 Trieste. You’ll stay here for 1 night.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most beloved attractions included on the itinerary is Porta San Giovanni. This picture-perfect monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo and learn what makes this UNESCO world heritage-designated public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Rocca Di Montestaffoli. After exploring the castle, head to Parco Della Rocca. This worthwhile park is a highlight in Siena.

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 you explore more of Trieste, 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 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.

If you’re not ready to end the night just yet, "life" New Bar Torinese Snc offers a perfect venue to relax and savor a drink. Similarly, White Cafe is well-suited for those looking to unwind in a social setting. Café James Joyce is another excellent spot to enjoy a nightcap after a delightful meal.

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