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 get the chance to experience Miramare / Miramar and Trieste. At the end of the day, you'll drive back to Trieste, where you still have 1 night left to stay.

Canale Ponterosso Trieste is perfect for a self-paced visit during the day. This romantic street is sure to impress. Next on your list is Piazza Della Borsa, another must-visit landmark and beloved public square renowned for its romantic features.

While exploring and sightseeing, take time to savor the culture of Trieste by sampling some local delicacies. When you’re ready for more sightseeing, head to Roman Theatre Of Trieste. This respected archeological site is an essential place to visit for anyone looking for the full Trieste experience. We also recommend visiting Piazza Unità D'italia, an interesting public square. Nearby, you'll also find Revoltella Museum, ready to add charm to your journey.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Miramare / Miramar. This drive usually takes around 18 min, without any stops or traffic disruptions.

Our first attraction recommendation in Miramare / Miramar is Miramare Castle, a locally renowned castle that draws attention for its visually striking features.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Trieste, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal 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.

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!

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Venice. At the end of the day, you’ll unwind at one of the finest accommodations in Venice, where you'll spend 1 night.

Continue your road trip and head to your next destination, Venice. This car ride takes around 2 hours 17 min.

Spend your afternoon discovering Bridge Of Sighs, a notable monument known for its history-steeped features. Next, continue your sightseeing at Doge's Palace, a locally renowned palace.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by St Mark's Basilica and uncover the details of this symbolic church. Make sure to also explore Piazza San Marco, a wondrous public square. For your last stop, consider Grand Canal, a romantic street that many travelers find worth the detour.

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

Venice is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Venice.

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.

After enjoying a fulfilling meal, continue your evening at Al Parlamento, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Caffe Rosso offers a welcoming atmosphere for easing into the nightlife. Similarly, Adagio 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 Italy.

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 2 nights.

Florence’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Venice behind. This drive usually takes around 2 hours 52 min. Florence welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Galleria Dell'accademia, a captivating art gallery that everyone visiting Florence should see. Next, head to Basilica Of Santa Croce In Florence. This heritage-rich church is one of the most popular attractions in the region.

If you're keen to see more, don’t miss out on Uffizi Gallery, a standout art gallery popular among locals as well as travelers. Ponte Vecchio is an excellent attraction to visit next. Spend some time learning more about this timeless historical landmark before you continue your journey. Lastly, visit Piazza Della Repubblica, a romantic public square and a top attraction in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Savor another day of unforgettable experiences in Italy!

On day 5 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa to the fullest today with this curated day itinerary.

Pisa is brimming with adventures.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 1 hour 16 min.

Spend your afternoon discovering Piazza Del Duomo, Pisa, a timeless public square known for its historic features. Next, continue your sightseeing at Campo Santo, an increasingly popular cemetery.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Pisa Cathedral and uncover the details of this UNESCO world heritage-listed church. Make sure to also explore Leaning Tower Of Pisa, an iconic monument. For your last stop, consider Museo Dell'opera Del Duomo, a photogenic museum that many travelers find worth the detour.

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

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

Don’t miss out on dining 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.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Siena and San Gimignano. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 2 nights.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 10 min. When you arrive in Siena, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Fortezza Medicea (siena). Spend some time admiring the picture-perfect features of the monument before you continue to your next stop. Then, head to Tower Of Mangia. This worthwhile monument is a traveler-favorite in the city.

If you're keen to see more, continue to Piazza Del Campo. Feed your curiosity by learning something new about the public square. Next, take your journey to Siena Cathedral, a locally renowned church.

It’s time to gear up for the next part of your road trip adventure. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Parco Della Rocca, a beloved park known for its history-steeped features. Next, continue your sightseeing at Piazza Del Duomo, an increasingly popular public square.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

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.

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

Greet day 7 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Siena, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Greve in Chianti, Greti, and Montepulciano.

Set your GPS to Greve in Chianti and hit the road. Expect a journey of approximately 1 hour 2 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greve in Chianti beckons with new experiences!

Set out on a self-guided sightseeing tour at Castle Of Verrazzano and explore the history-steeped features.

Set your GPS to Greti and hit the road. Expect a journey of approximately 7 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greti beckons with new experiences!

Villa Calcinaia - Conti Capponi is an underrated winery we recommend visiting today. Discover its romantic features before continuing your self-guided tour.

Montepulciano’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Greti behind. This drive usually takes around 1 hour 45 min. Montepulciano welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Az. Agr. Crociani Susanna Crociani, an intriguing winery that everyone visiting Montepulciano should see. Next, head to Fortezza Medicea. This romantic castle is one of the most up-and-coming attractions in the region.

If you're keen to see more, don’t miss out on Porta Al Prato, a heritage-rich monument popular among locals as well as travelers.

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

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

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

Unwind after your meal by stepping into Charlie Mixology Bar Di Aldinucci Riccardo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Pinacoteca offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook San Paolo Pub, another top-rated bar in the area.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Bologna are on today's agenda. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Bologna may take around 2 hours 4 min. Upon your arrival in Bologna, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Our first attraction recommendation in Bologna is Palazzo Re Enzo, a beloved palace that draws attention for its picture-perfect features. Spend some time soaking in the atmosphere before continuing to Fountain Of Neptune, Bologna, a standout monument that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Bologna Cathedral, an up-and-coming church that offers a unique experience. Be sure to also explore Two Towers, a nearby monument, highly recommended by other travelers. End your self-guided tour at Piazza Santo Stefano, a grand public square and the perfect final attraction in Bologna.

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

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.

Enjoy a delicious meal at Ristorante Ciacco, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Ristorante Ballarini, another top spot with a tantalizing menu. You might also want to secure a reservation at Sfoglia Rina. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

After your meal, keep the night alive at a bar like Bar Al Bricco D'oro, known for its lively atmosphere. Bar Freud E Squisito is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Osteria Del Sole offers an excellent atmosphere for those looking to amp up the evening.

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

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Trieste, where you'll spend 1 night.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Verona. Your travel time is around 1 hour 47 min.

Savor the day by heading to Castelvecchio Museum, an interesting museum that draws visitors from near and far. When you're done, continue to Castelvecchio Bridge, where you can soak in the awe-inspiring surroundings.

Next, explore Verona Arena, yet another iconic place to see in the area. After the stadium, make time to go to Porta Borsari. This instagrammable historical landmark is well worth the visit. Lastly, head to Piazza Delle Erbe, a captivating public square you won’t want to miss.

When you’re done exploring for the day, you’ll drive to your hotel in Trieste. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Trieste's most popular restaurants, and connect with friendly locals for a true cultural experience.

Treat yourself to a delightful dinner at Caffè degli Specchi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria Istriano Of Giobi And Oxa? It's another excellent option with a diverse menu. Consider reserving a table at Chimera di Bacco as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Trieste.

After your delicious meal, get a taste of the vibrant nightlife with a visit to "life" New Bar Torinese Snc, known for its inviting atmosphere. White Cafe is another great option if you’re looking for a place to get the night started. Similarly, Café James Joyce 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!