11-Day Italy Self-Drive Road Trip With Itinerary from Trieste traveling west to Venice, Florence, and Siena

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

Savor the day by visiting some of the best places to see in Trieste, including a castle, a pier, a public square, an archeological site, a church and much more! Start your adventure at Miramare Castle. This well-known castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Molo Audace located in Trieste for another exciting encounter.

Next, immerse yourself in the setting of Piazza Unità D'italia. Its respected features will captivate you. After the public square, continue your tour of the village with a visit to Roman Theatre Of Trieste. Visitors usually appreciate the breathtaking features of this archeological site. Next up is Cattedrale Di San Giusto Martire, a highly recommended church. For a change of pace, head to Civico Museo Del Castello Di San Giusto. As one of the most increasingly popular attractions in Trieste, this castle is the perfect place to end your self-guided sightseeing tour.

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

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

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.

Keep the excitement of the evening going by visiting a bar or two. Mast is an excellent place to start. You could also check out Urbanis, offering a different kind of charm. A last recommendation for the day is Coktail Bar Trieste | La Preferita. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Celebrate another amazing day of your road trip adventure in Italy!

On day 3 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 Venice. In the evening, you’ll end up in Venice, where you will stay for 2 nights.

Get ready for an exciting day in Trieste. Today’s sightseeing agenda includes a monument, a palace, a church, a public square, an opera house, a historical landmark and much more! Begin your adventure at Bridge Of Sighs. This is a popular monument you should not miss. Another must-see is Doge's Palace, a popular palace in Trieste.

When you’re ready for the next sight, head to St Mark's Basilica. From there, take a leisurely stroll to Piazza San Marco, another of the city’s globally renowned attractions. We recommend continuing your self-guided tour at Teatro La Fenice, a romantic place of interest in the city. If time allows, add Rialto Bridge to your itinerary. This globally renowned historical landmark offers the perfect finishing touch to your day in Trieste.

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

Have a fantastic dining experience at Bauer Hotel, a highly recommended choice for tonight's dinner. If you're looking to mix things up, L'Osteria Le Guglie offers an enticing alternative with its varied menu. Additionally, Corner Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

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

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

Day 4 of your road trip will take you to the best attractions Venice has to offer. Cherish the 1 night you have left in Venice by discovering the best things there are to see and do in the city.

At the top of the list of things to do today is to explore Cannaregio, a neighborhood that captures the true essence of Venice. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the curiosity-inducing Santa Maria Della Salute, a history-steeped church in Venice. Next, go to Peggy Guggenheim Collection.

After visiting Santa Maria Della Salute and Peggy Guggenheim Collection, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to Gallerie Dell'accademia. This historic art gallery offers a unique experience. Santa Maria Gloriosa Dei Frari is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Grand Canal, one of the most enchanting places to visit in Venice.

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.

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

Enjoy a delicious meal at Generator Venice, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Nevodi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

After enjoying a fulfilling meal, continue your evening at Il Mercante, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Irish Pub Venezia offers a welcoming atmosphere for easing into the nightlife. Similarly, Ai Stagneri provides an excellent environment for a relaxed and enjoyable evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Padua, Bologna, and Florence, 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 Florence. You’ll stay here for 3 nights.

Today’s itinerary in Venice covers several incredible sights, including a church, a public square, a monument, an art gallery and much more! Start your adventure at The Basilica Of St. Anthony. This locally renowned church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Prato Della Valle, a must-see public square 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 Two Towers. This well-known monument offers an enriching experience. For a change of pace, head to Piazza Maggiore, where you can take in awe-inspiring features. Conclude your self-guided sightseeing tour with a visit to Galleria Dell'accademia and Cathedral Of Santa Maria Del Fiore. These sights offer a fulfilling end to a perfect day.

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.

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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 6 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Savor the day by visiting some of the best places to see in Florence, including an observation deck, a church, a public square, a palace, an art gallery, a historical landmark and much more! Start your adventure at Piazzale Michelangelo. This astonishing observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Of Santa Croce In Florence located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Della Signoria. Its detailed features will captivate you. After the public square, continue your tour of the city with a visit to Palazzo Vecchio. Visitors usually appreciate the visually striking features of this palace. Next up is Uffizi Gallery, a highly recommended art gallery. For a change of pace, head to Ponte Vecchio. As one of the most world-famous attractions in Florence, this historical landmark is the perfect place to end your self-guided sightseeing tour.

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.

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Celebrate another amazing day of your road trip adventure in Italy!

Wake up to day 7 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Battistero Di San Giovanni, a locally appreciated church in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this UNESCO world heritage-listed public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Campo Santo. This is one of the city’s most increasingly popular culturally significant spots of interest. After exploring the cemetery, visit the up-and-coming Pisa Cathedral. Not far away, you'll also find Leaning Tower Of Pisa. This monument is an UNESCO world heritage-designated highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Knights' Square, a curiosity-inducing public square in the city.

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

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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing 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.

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 - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Today’s agenda in Florence includes a monument, a church, a palace, a public square and much more! Fortezza Medicea (siena) is must-visit monument and a great starting point for the day. Next, continue your journey to Basilica Of San Domenico, an intriguing church, located just a leisurely stroll away. Next, head to Siena Cathedral, an enchanting church, 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 locally appreciated Pubblico Palace. If you’re looking for more, Piazza Del Campo is also an astonishing attraction that is worthwhile a visit. Lastly, don’t miss Tower Of Mangia, a place of UNESCO world heritage-designated interest in the city.

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 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 meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 9 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Siena, San Quirico d'Orcia, Buonconvento, Monte Oliveto Maggiore, and Asciano. You still have 1 night left in Siena.

Today’s well-planned self-sightseeing route offers several fun adventures, picturesque spots, and history-rich sites. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Palazzo Salimbeni is the first of them. Spend some time admiring this standout palace before continuing your journey. Porta Romana is your next stop. This intriguing monument is one of the best-rated sights in Siena.

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 Cipressi Di San Quirico D'orcia. This mesmerizing rock formation is a sight to behold. To round off your sightseeing experience, visit Museo Della Mezzadria Senese and Abbazia Di Monte Oliveto Maggiore.

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

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.

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Explore the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Pinacoteca for a great selection of flavorful drinks and a charming setting. Furthermore, San Paolo Pub is perfect for those looking to extend their night with a touch of local flavor.

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

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Bologna and 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.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Porta Castiglione. This heritage-rich monument is sure to ignite your curiosity. Next, dive into the standout features of Porta Borsari, a must-visit historical landmark 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 Verona Arena, a timeless stadium. For a change of scene, check out Gran Guardia, known for its heritage-rich features.

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.

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.

If you’re not ready to end the night just yet, "life" New Bar Torinese Snc offers a perfect venue to relax and savor a drink. Similarly, White Cafe is well-suited for those looking to unwind in a social setting. Café James Joyce is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences in Italy!