10-Day Italy Self-Drive Road Trip With Itinerary from Trieste to Venice, Florence, Siena, and Bologna

On day 2 of your road trip, you will have an entire day to explore Miramare / Miramar. You’ll stay in Trieste for 1 night and discover all the best things to see and do in the area.

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 instagrammable castle before continuing your journey. Molo Audace is your next stop. This locally appreciated pier 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 Unità D'italia. This standout public square is a sight to behold. To round off your sightseeing experience, visit Piazza Della Borsa and Grotta Gigante.

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.

Experience shopping bliss at Trieste as you explore Il Giulia Shopping Center. Take a leisurely stroll through unique and shops, where local treasures are waiting to be found. Beyond shopping, Il Giulia Shopping Center offers more options, including a cinema, restaurants, unique attractions, key services, and vibrant events.

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.

Don’t miss out on dining at Rustiko, a top-rated dining destination in Trieste. If you're in the mood to try something new, consider Caffè San Marco, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria Marise. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Trieste this evening.

Continue your lively evening at Mast, a perfect place for winding down or revving up the night, depending on which mood you’re in. Urbanis is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Coktail Bar Trieste | La Preferita ensures a night out tailored to your taste.

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.

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Venice. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 1 night.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Bridge Of Sighs. This captivating monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Doge's Palace, one of the city’s most promising highlights.

Next, check out St Mark's Basilica, one of the most interesting places to see in Trieste. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza San Marco. Wander around and soak in the visually striking atmosphere this public square offers. Finally, take the path to the iconic Rialto Bridge, the last of our attraction recommendations for today.

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.

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.

Make sure to reserve a table at Bauer Hotel, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of L'Osteria Le Guglie, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corner Pub, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Al Parlamento, a top-rated bar in the area. For other recommendations, The Caffe Rosso provides a perfect setting for rounding out your night with style and great drinks. Likewise, Adagio offers a memorable night with diverse drink options and excellent service.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Ponte Vecchio. This wondrous historical landmark provides an insightful glimpse into the city's identity. Next, discover Piazza Della Repubblica, a visually striking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Cathedral Of Santa Maria Del Fiore, a famous church. When you’re done, don’t forget to make a stop at the widely recognized Piazza Della Signoria.

At the end of the day, you will drive to Florence, 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 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 Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

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

Greet day 5 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 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 Pisa.

Florence is home to plenty of attractions that offer fun adventures, breathtaking views, and photo-friendly spots! Start at Piazza Del Duomo, Pisa, an iconic public square that is worthwhile a visit in the city. Nearby, you’ll find Pisa Cathedral, enchanting visitors with its grand appeal. Continue your exploration at Leaning Tower Of Pisa. This monument is one of the city’s most world-famous spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Knights' Square. After exploring the public square, head to the curiosity-inducing Palazzo Blu. This art gallery will wrap up today’s self-guided sightseeing tour in the city.

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

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

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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!

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Discover a day packed with fun adventures, scenic views, and picturesque spots in Florence. Begin your sightseeing with Fortezza Medicea (siena). This intriguing monument is one of the top attractions in the city. Proceed to Piazza Del Campo, another must-visit attraction that enhances the city’s allure.

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 well-known church is a traveler-favorite. Not far away, you’ll find Porta San Giovanni, another key site on your sightseeing itinerary. Conclude your day at Piazza Del Duomo and uncover why it's recognized as one of the city's most locally appreciated attractions.

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

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

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Savor another day of unforgettable experiences in Italy!

On day 7 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Savor the day by visiting some of the best places to see in Siena, including a monument, a winery, and a castle. Start your adventure at Porta Al Prato. This underrated monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Az. Agr. Crociani Susanna Crociani located in Siena for an enchanting atmosphere.

Next, immerse yourself in the setting of Fortezza Medicea. Its history-steeped features will captivate you.

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

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

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena. If you're in the mood for something new, try Fischi per Fiaschi, another premier location with a delectable menu. You might also want to book a table at Osteria da Divo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Charlie Mixology Bar Di Aldinucci Riccardo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Pinacoteca offers an ideal atmosphere to enjoy the pleasures of the night. San Paolo Pub is also a great option that provides a perfect setting for a relaxing evening.

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

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Bologna. You’ll stay here for 1 night.

Savor the day by visiting some of the best places to see in Siena, including a public square, a monument, and a church. Start your adventure at Piazza Santo Stefano. This intriguing public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Two Towers located in Siena for an enchanting atmosphere.

Next, immerse yourself in the setting of Bologna Cathedral. Its breathtaking features will captivate you. After the church, continue your tour of the city with a visit to Fountain Of Neptune, Bologna. This monument has a heritage-rich appeal. For a change of pace, head to Piazza Maggiore. As one of the most widely recognized attractions in Siena, this public square is an excellent place to end your self-guided tour.

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.

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.

Treat yourself to a delightful dinner at Ristorante Ciacco, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Ballarini? It's another excellent option with a diverse menu. Consider reserving a table at Sfoglia Rina as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise your glass to another unforgettable day in Italy!

On day 9 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 Trieste, where you will stay for 1 night.

Bologna is brimming with adventures. Today’s wonderful stops include a stadium, a public square, and a historical landmark. Begin your sightseeing adventure at the wondrous Verona Arena. Just a short distance away is Piazza Delle Erbe, a romantic public square that draws visitors from far and near.

Continue your journey to Piazza Dei Signori, one of the city’s most increasingly popular spots that you shouldn’t miss. Another great site to visit is the popular Ponte Pietra.

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 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 Caffè degli Specchi, 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 Osteria Istriano Of Giobi And Oxa, 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 Chimera di Bacco. It’s yet another ideal choice to enhance your time in Trieste tonight.

Keep the excitement of the evening going by visiting a bar or two. "life" New Bar Torinese Snc is an excellent place to start. You could also check out White Cafe, offering a different kind of charm. A last recommendation for the day is Café James Joyce. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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