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

Wake up to day 2 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Miramare / Miramar and Trieste. With 1 night to stay in Trieste, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Whether you decide to explore Miramare / Miramar on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Your adventure in Trieste is only getting started when you visit Miramare Castle, a popular local hot spot. Another notable attraction to explore is Molo Audace. This often recommended pier is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Trieste's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Unità D'italia. This romantic public square offers a fascinating experience that many visitors find memorable. Roman Theatre Of Trieste is also worth visiting, along with Cattedrale Di San Giusto Martire. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Civico Museo Del Castello Di San Giusto. This often recommended castle provides a fitting finale to your sightseeing.

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 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 evening going at Mast, a great choice for enjoying the after-dinner hours with a drink. You could also go to Urbanis, which offers a similarly pleasant setting and great drinks. Another option is Coktail Bar Trieste | La Preferita, which provides an inviting environment for unwinding after a busy day out.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Venice. When you’re not sightseeing, take time to relax at your chosen hotel in Venice, where you’ll be staying for 2 nights.

Start your day at Bridge Of Sighs. This enchanting monument is a popular place to see in Trieste. Then, wander over to Doge's Palace. If enchanting sites excite you, this palace will be right up your alley. Nearby, you’ll also find St Mark's Basilica. This romantic church is a favorite among visitors.

Trieste offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza San Marco is a globally renowned spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the romantic Teatro La Fenice. Take a moment to appreciate the fascinating details of this well-known opera house. Wrap up your self-guided tour of Trieste's top attractions with a visit to Rialto Bridge.

When you’re done exploring for the day, you’ll drive to your hotel in Venice. Check in and relax 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.

Enjoy a delicious meal at Bauer Hotel, a highly-rated dining destination in Venice. If you're eager to try something different, consider L'Osteria Le Guglie, another top spot with a tantalizing menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

To truly maximize your evening out, consider visiting Al Parlamento after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to The Caffe Rosso, another bar with an inviting ambiance. Similarly, Adagio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Celebrate another amazing day of your road trip adventure 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 the city and use the provided itinerary to discover what to see in Venice.

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.

To truly experience Venice, make sure to drop by Santa Maria Della Salute. This beloved church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Peggy Guggenheim Collection, one of the city’s best highlights.

Next, check out Gallerie Dell'accademia, one of the most intriguing places to see in Venice. This art gallery is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Santa Maria Gloriosa Dei Frari. Wander around and soak in the historic atmosphere this church offers. Then, head to Grand Canal, a top-rated street that adds another dimension to your day.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Dine in style at Generator Venice, a top recommendation for dinner tonight. Or, for a change of pace, Nevodi boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Piazza. Known as a local hotspot, it’s a great choice for tonight in Venice.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Il Mercante, a well-loved spot among locals and tourists. Or, head to The Irish Pub Venezia. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ai Stagneri, another top-rated place in the area.

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

Your itinerary for day 5 of your road trip in Italy includes 3 stops and features some of the highlights of Padua, Bologna, and Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 3 nights.

The Basilica Of St. Anthony leaves a lasting impression. This church is one of the most popular places to visit in Venice. Next, head to Prato Della Valle, a notable public square, known for its history-steeped 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 Two Towers. This breathtaking monument is a highly recommended experience. Nearby, you'll also find Piazza Maggiore and Galleria Dell'accademia. Visit these for an interesting touch to your journey. Finish the day with a visit to Cathedral Of Santa Maria Del Fiore, an enchanting church in Venice.

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.

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 6 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 2 nights.

Make a stop at Piazzale Michelangelo. This spectacular 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 romantic 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 timeless 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 experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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

On day 7 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Start your day at Battistero Di San Giovanni. This breathtaking church is a locally appreciated place to see in Florence. Then, wander over to Piazza Del Duomo, Pisa. If breathtaking sites excite you, this public square will be right up your alley. Nearby, you’ll also find Campo Santo. This picture-perfect cemetery is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pisa Cathedral is an often recommended spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the UNESCO world heritage-listed Leaning Tower Of Pisa. Take a moment to appreciate the fascinating details of this wondrous monument. Wrap up your self-guided tour of Florence's top attractions with a visit to Knights' Square.

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

Florence 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 Florence.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

After your meal, keep the night alive at a bar like Gosh*, known for its lively atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Quelo Bar offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences 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 place, which are Siena. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 2 nights.

Awaiting your discovery is the frequently visited Fortezza Medicea (siena), a picture-perfect monument in Florence. Next, go to Basilica Of San Domenico.

After visiting Fortezza Medicea (siena) and Basilica Of San Domenico, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Siena Cathedral. This romantic church offers a unique experience. Pubblico Palace is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Del Campo, one of the most romantic places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Tower Of Mangia.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

If you’re not ready to end the night just yet, Meet Life Cafè offers a perfect venue to relax and savor a drink. Similarly, Maudit Pub is well-suited for those looking to unwind in a social setting. Bar Impero Siena is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 9 of your road trip, you'll get the chance to experience Siena, San Quirico d'Orcia, Buonconvento, Monte Oliveto Maggiore, and Asciano. At the end of the day, you'll drive back to Siena, where you still have 1 night left to stay.

Make time for Palazzo Salimbeni, a frequently visited palace that is worthwhile a visit in the city. Nearby, you’ll find Porta Romana, enchanting visitors with its stunning appeal. Continue your exploration at Cipressi Di San Quirico D'orcia. This rock formation is one of the city’s most underrated 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 Museo Della Mezzadria Senese. After exploring the museum, head to the intriguing Abbazia Di Monte Oliveto Maggiore.

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

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

Have a fantastic dining experience at Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pinacoteca, a bar catering to every mood and preference. San Paolo Pub likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 10 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Bologna and Verona are on today's agenda. In the evening, you’ll end up in Trieste, where you will stay for 1 night.

Let Porta Castiglione set the tone for the day. Spend some time admiring this culturally significant monument before continuing your journey. Porta Borsari is your next stop. This locally appreciated historical landmark 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 Verona Arena. This visually striking stadium is a sight to behold. To round off your sightseeing experience, visit Gran Guardia.

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.

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.

Enjoy a delicious meal 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.

Continue the enjoyment post-dinner at "life" New Bar Torinese Snc, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, White Cafe offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Café James Joyce. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day in Italy!