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

On day 2 of your road trip, you’ll start and end your day in Trieste, where you'll stay for 1 night more.

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

When you’re ready for the next sight, head to Piazza Della Borsa. From there, take a leisurely stroll to Roman Theatre Of Trieste, another of the village’s frequently visited attractions. We recommend continuing your self-guided tour at Piazza Unità D'italia, a visually striking place of interest in the village. If time allows, add Revoltella Museum to your itinerary. This underrated museum offers the perfect finishing touch to your day in Trieste.

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.

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.

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

Raise your glass to another unforgettable day 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 1 night.

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 locally renowned Bridge Of Sighs and allow yourself time to explore. Just a short distance away you'll find your next stop, Doge's Palace, a visually striking palace that draws visitors from far and near.

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

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

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.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Caffe Rosso, a bar catering to every mood and preference. Adagio likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 4 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 2 nights.

Today's adventure in Venice promises more breathtaking discoveries and enriching experiences! Begin at Galleria Dell'accademia. This standout art gallery is a highlight of any visit in the city. Then, enjoy Basilica Of Santa Croce In Florence, another culturally significant attraction that never fails to captivate visitors. Next, head over to Uffizi Gallery, one of the city’s most widely recognized attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Ponte Vecchio. This visually striking historical landmark is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Della Repubblica, a captivating public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Della Signoria before you head back to your hotel.

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.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

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

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

Today’s itinerary in Florence covers several incredible sights, including a public square, a cemetery, a church, a monument, a museum and much more! Start your adventure at Piazza Del Duomo, Pisa. This wondrous public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Campo Santo, a must-see cemetery 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 Pisa Cathedral. This intriguing church offers an enriching experience. For a change of pace, head to Leaning Tower Of Pisa, where you can take in picture-perfect features. Conclude your self-guided sightseeing tour with a visit to Museo Dell'opera Del Duomo and Knights' Square. These sights offer a fulfilling end to a perfect day.

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

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

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

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 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Today’s agenda in Florence includes a monument, a public square, a church, a park and much more! Fortezza Medicea (siena) is must-visit monument and a great starting point for the day. Next, continue your journey to Tower Of Mangia, an underrated monument, located just a leisurely stroll away. Next, head to Piazza Del Campo, a history-steeped public square, 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 popular Siena Cathedral. If you’re looking for more, Parco Della Rocca is also a curiosity-inducing attraction that is worthwhile a visit. Lastly, don’t miss Piazza Del Duomo, a place of visually striking 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.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 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.

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

On day 7 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience Greve in Chianti, Greti, and Montepulciano to the fullest today with this curated day itinerary!

Get ready to discover some of the most iconic wonders in Siena, including a castle, a winery, and a monument. Start your day at Castle Of Verrazzano. This visually striking castle is an often recommended place to see in Siena. Then, wander over to Villa Calcinaia - Conti Capponi. If romantic sites excite you, this winery will be right up your alley. Nearby, you’ll also find Az. Agr. Crociani Susanna Crociani. This romantic winery is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Fortezza Medicea is a beloved spot in the town that will captivate you with its unique charm. When you’re done at the castle, don’t forget to check out the photogenic Porta Al Prato. Take a moment to appreciate the fascinating details of this intriguing monument.

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

As you explore more of Siena, 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 dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, 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 da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

To truly maximize your evening out, consider visiting Charlie Mixology Bar Di Aldinucci Riccardo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Pinacoteca, another bar with an inviting ambiance. Similarly, San Paolo Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Experience an unparalleled adventure on day 8 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.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Palazzo Re Enzo. This breathtaking palace is sure to ignite your curiosity. Next, dive into the noteworthy features of Fountain Of Neptune, Bologna, a must-visit monument 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 Bologna Cathedral, an intriguing church. For a change of scene, check out Two Towers, known for its breathtaking features. We also recommend visiting Piazza Santo Stefano. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazza Maggiore, yet another top-rated attraction in Siena.

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.

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

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

After enjoying a fulfilling meal, continue your evening at Bar Al Bricco D'oro, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Freud E Squisito offers a welcoming atmosphere for easing into the nightlife. Similarly, Osteria Del Sole provides an excellent environment for a relaxed and enjoyable evening.

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 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.

Discover a day packed with fun adventures, scenic views, and photo-friendly spots in Bologna. Begin your sightseeing with Castelvecchio Museum. This locally renowned museum is one of the top attractions in the city. Proceed to Castelvecchio Bridge, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Verona Arena. This iconic stadium is a traveler-favorite. Not far away, you’ll find Porta Borsari, another key site on your sightseeing itinerary. Piazza Delle Erbe is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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 Caffè degli Specchi, a top-rated dining destination in Trieste. If you're in the mood to try something new, consider Osteria Istriano Of Giobi And Oxa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Chimera di Bacco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Trieste this evening.

Unwind after your meal by stepping into "life" New Bar Torinese Snc. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, White Cafe offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Café James Joyce, another top-rated bar in the area.

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