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, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Miramare / Miramar and Trieste. You still have 1 night left in Trieste.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Miramare Castle. This popular castle is an enchanting place to see in Trieste. Continue your discovery at Canale Ponterosso Trieste, a history-steeped street with stories to tell.

As you stroll around Trieste, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Piazza Della Borsa. This beloved public square offers a historic encounter with Trieste. Next, make your way to Roman Theatre Of Trieste to add another highlight to your day. After that, visit Piazza Unità D'italia, a captivating public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Revoltella Museum, an often recommended museum in the village. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Trieste.

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

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

Enjoy a delicious meal at Rustiko, a highly-rated dining destination in Trieste. If you're eager to try something different, consider Caffè San Marco, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria Marise. With a reputation for consistently satisfying customers, it’s an excellent 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.

Raise your glass to another unforgettable day in Italy!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Venice. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 1 night.

Today's adventure in Trieste promises more breathtaking discoveries and enriching experiences! Begin at Bridge Of Sighs. This visually striking monument is a highlight of any visit in the city. Then, enjoy Doge's Palace, another visually striking attraction that never fails to captivate visitors. Next, head over to St Mark's Basilica, one of the city’s most interesting attractions, known for its UNESCO world heritage-listed features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza San Marco. This history-steeped public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Grand Canal, an underrated street, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Rialto Bridge before you head back to your hotel.

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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Venice. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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.

Extend your evening after a delightful meal by visiting Al Parlamento, which offers the perfect atmosphere for a night out. Moreover, The Caffe Rosso is another popular option for a drink or two. Likewise, Adagio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Say good night to Venice and look forward to another great day of your road trip 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.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and historic treasures. 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. Galleria Dell'accademia is the first of them. Spend some time admiring this heritage-rich art gallery before continuing your journey. Basilica Of Santa Croce In Florence is your next stop. This popular 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 Uffizi Gallery. This standout art gallery is a sight to behold. To round off your sightseeing experience, visit Ponte Vecchio and Piazza Della Repubblica. If time allows, end your day with Piazza Della Signoria, a history-steeped public square that offers a memorable conclusion to your exploration.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence's best restaurants.

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.

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.

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

On day 5 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Del Duomo, Pisa. This symbolic public square is sure to ignite your curiosity. Next, dive into the remarkable features of Campo Santo, a must-visit cemetery 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 Pisa Cathedral, an increasingly popular church. For a change of scene, check out Leaning Tower Of Pisa, known for its culturally significant features. We also recommend visiting Museo Dell'opera Del Duomo. This museum is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Knights' Square, yet another underrated attraction in Florence.

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.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Siena and 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 Siena. You’ll stay here for 2 nights.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most worthwhile attractions included on the itinerary is Fortezza Medicea (siena). This instagrammable monument will help you start your sightseeing on top. Then, take a leisurely stroll to Tower Of Mangia and learn what makes this UNESCO world heritage-listed monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the spectacular Piazza Del Campo. After exploring the public square, head to Siena Cathedral. This captivating church is a highlight in Florence. As your day continues, stop by Parco Della Rocca, known for its history-steeped features. Lastly, don’t forget to check out the locally appreciated Piazza Del Duomo. Enjoy exploring this incredible public square at your own pace.

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.

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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Celebrate another amazing day of your road trip adventure 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Castle Of Verrazzano. This worthwhile castle provides an insightful glimpse into the town's identity. Next, discover Villa Calcinaia - Conti Capponi, a visually striking winery, promising a delightful encounter.

Continue your sightseeing with a visit to Az. Agr. Crociani Susanna Crociani, a beloved winery. When you’re done, don’t forget to make a stop at the intriguing Fortezza Medicea. Round off your day at Porta Al Prato, another gem in Siena with culturally significant features to discover.

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

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

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.

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.

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

On day 8 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 Bologna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Siena is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and photo-friendly spots! Start at Palazzo Re Enzo, a beloved palace that is worthwhile a visit in the city. Nearby, you’ll find Fountain Of Neptune, Bologna, enchanting visitors with its symbolic appeal. Continue your exploration at Bologna Cathedral. This church is one of the city’s most curiosity-inducing spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Two Towers. After exploring the monument, head to the increasingly popular Piazza Santo Stefano. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Maggiore, a place of visually striking interest in Siena.

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.

As you explore more of Bologna, 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 delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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.

Raise your glass and celebrate another amazing day of your road trip 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 Verona. At the end of the day, you will enjoy the comforts of a top-rated hotel in Trieste, which will be your home away from home for 1 night.

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Castelvecchio Museum is the perfect place to start. This museum is one of the most popular places to visit in Bologna. Next, head to Castelvecchio Bridge, an interesting monument, known for its culturally significant features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Verona Arena. This visually striking stadium is a highly recommended experience. Nearby, you'll also find Porta Borsari and Piazza Delle Erbe. Visit these for an interesting touch to your journey.

When you’re done exploring for the day, you’ll drive to your hotel in Trieste. Check in and spend some time relaxing 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 an authentic adventure.

Savor the flavors at Caffè degli Specchi, a top pick for dinner tonight. Alternatively, Osteria Istriano Of Giobi And Oxa beckons with its unique menu offerings. Also, consider Chimera di Bacco. With its consistent customer satisfaction, it’s an excellent option for dining in Trieste tonight.

Cap off your dinner by heading to "life" New Bar Torinese Snc, ideal for a leisurely evening with a drink in hand. White Cafe is another bar that offers an enjoyable setting. Similarly, Café James Joyce is also a popular place to go on a night out, perfect for relaxing and socializing.

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