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

Greet day 2 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Trieste 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 Miramare / Miramar and Trieste.

Brace yourself for today’s incredible lineup of attractions in Trieste, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Miramare Castle, a captivating castle in the village. Then, head to Canale Ponterosso Trieste and soak in the ambiance of this visually striking street.

There are many interesting places to see in Trieste, and when you are ready for more, go to Piazza Della Borsa. This is one of the village’s most underrated picture-perfect spots of interest. After exploring the public square, visit the locally appreciated Roman Theatre Of Trieste. Not far away, you'll also find Piazza Unità D'italia. This public square is a history-steeped highlight in Trieste. Before wrapping up your self-guided sightseeing tour, head to Revoltella Museum, an up-and-coming museum in the village.

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

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

Enjoy a lovely meal at Rustiko, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè San Marco is another top choice with a popular menu. You could also check for a table at Osteria Marise. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Trieste tonight.

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.

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.

Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Bridge Of Sighs. This popular 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 best 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 culturally significant atmosphere this public square offers. Then, head to Grand Canal, a top-rated street that adds another dimension to your day. Finally, visit the wondrous Rialto Bridge, the last of our attraction recommendations for today.

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.

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.

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.

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.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

A blend of family-friendly attractions, photo-friendly spots, and historic treasures await you in Venice on today’s itinerary. First up is the well-known art gallery, Galleria Dell'accademia. Afterward, continue to Basilica Of Santa Croce In Florence, a church every traveler should visit.

As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Uffizi Gallery. This widely recognized art gallery is an essential stop. Following that, head to Ponte Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Della Repubblica, a notable public square in the city. Finally, end your day with a visit to Piazza Della Signoria, a visually striking public square that offers the perfect conclusion to your sightseeing of the 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 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 delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo, Pisa. This breathtaking public square is a highlight of any visit in the city. Then, enjoy Campo Santo, another masterful attraction that never fails to captivate visitors. Next, head over to Pisa Cathedral, one of the city’s most intriguing attractions, known for its stunning features.

If you’re looking for more, spend time soaking in the atmosphere of Leaning Tower Of Pisa. This picture-perfect monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Museo Dell'opera Del Duomo, an intriguing museum, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Knights' Square before you head back to your hotel.

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

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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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 6 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 and San Gimignano. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Discover a day packed with fun adventures, breathtaking views, and picturesque spots in Florence. Begin your sightseeing with Fortezza Medicea (siena). This increasingly popular monument is one of the top attractions in the city. Proceed to Tower Of Mangia, another must-visit attraction.

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 Piazza Del Campo. This extraordinary public square is a traveler-favorite. Not far away, you’ll find Siena Cathedral, another key site on your sightseeing itinerary. Parco Della Rocca is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Duomo and uncover why it's recognized as one of the city's most underrated attractions.

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.

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

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.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day 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!

Today’s itinerary in Siena covers several incredible sights, including a castle, a winery, and a monument. Start your adventure at Castle Of Verrazzano. This often recommended castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the stunning wonders of Villa Calcinaia - Conti Capponi, a must-see winery in the town.

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 Az. Agr. Crociani Susanna Crociani. This up-and-coming winery offers an enriching experience. For a change of pace, head to Fortezza Medicea, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Porta Al Prato. These sights offer a fulfilling end to a perfect day.

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

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

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.

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

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the beloved Palazzo Re Enzo, a picture-perfect palace in Siena. Next, go to Fountain Of Neptune, Bologna.

After visiting Palazzo Re Enzo and Fountain Of Neptune, Bologna, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Bologna Cathedral. This picture-perfect church offers a unique experience. Two Towers is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Santo Stefano, one of the most enchanting places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by Piazza Maggiore.

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.

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

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.

Cap off your dinner by heading to Bar Al Bricco D'oro, ideal for a leisurely evening with a drink in hand. Bar Freud E Squisito is another bar that offers an enjoyable setting. Similarly, Osteria Del Sole 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!

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Verona. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Trieste. You will spend 1 night here for some well-deserved relaxation.

Today’s itinerary in Bologna covers several incredible sights, including a museum, a monument, a stadium, a historical landmark, a public square and much more! Start your adventure at Castelvecchio Museum. This locally renowned museum is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Castelvecchio Bridge, a must-see monument 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 Verona Arena. This timeless stadium offers an enriching experience. For a change of pace, head to Porta Borsari, where you can take in history-steeped features. Conclude your self-guided sightseeing tour with a visit to Piazza Delle Erbe. 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 Trieste. Trieste 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 Trieste. 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 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.

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.

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