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

Dive into day 2 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Trieste and Miramare / Miramar. At the end of the day, you’ll unwind at one of the finest accommodations in Venice, where you'll spend 2 nights.

To truly experience Trieste, make sure to drop by Cattedrale Di San Giusto Martire. This intriguing church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Roman Theatre Of Trieste, one of the city’s best highlights.

Next, check out Piazza Unità D'italia, one of the most notable places to see in Trieste. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Della Borsa. Wander around and soak in the romantic atmosphere this public square offers. Then, head to Canale Ponterosso Trieste, a top-rated street that adds another dimension to your day. Finally, visit the notable Miramare Castle, the last of our attraction recommendations for today.

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.

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 Venice, it's often a good idea to reserve a table in advance.

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

Let the evening flow smoothly from dinner to drinks at Al Parlamento, a top-rated bar in the area. For other recommendations, The Caffe Rosso provides a perfect setting for rounding out your night with style and great drinks. Likewise, Adagio offers a memorable night with diverse drink options and excellent service.

Relax and look forward to more memorable moments to come!

On day 3 of your road trip, you will have an entire day to discover what to see in Venice. You’ll stay in Venice for 1 night.

Make time for Bridge Of Sighs, a captivating monument that is worthwhile a visit in the city. Nearby, you’ll find Doge's Palace, enchanting visitors with its UNESCO world heritage-designated appeal. Continue your exploration at St Mark's Basilica. This church is one of the city’s most well-known spots.

Enjoy the freedom of exploring Venice at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza San Marco. After exploring the public square, head to the timeless Rialto Bridge. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Grand Canal, a place of UNESCO world heritage-designated interest in Venice.

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.

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.

Treat yourself to a delightful dinner at Generator Venice, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Nevodi? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante La Piazza as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Il Mercante stands out as an excellent choice for a post-dinner cocktail. Alternatively, The Irish Pub Venezia offers an ideal atmosphere to enjoy the pleasures of the night. Ai Stagneri is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass and celebrate another amazing 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 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 3 nights.

Awaiting your discovery is the often recommended Piazza Santo Stefano, a visually striking public square in Venice. Next, go to Two Towers.

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

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.

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.

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. Known for great service, it’s a fantastic choice for tonight in Florence.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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

Day 5 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Basilica Of Santa Croce In Florence makes a great addition to your morning plans. This interesting church is a culturally significant place to see in Florence. Continue your discovery at Palazzo Vecchio, a history-steeped palace with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Uffizi Gallery. This famous art gallery offers a romantic encounter with Florence. Next, make your way to Ponte Vecchio to add another highlight to your day. After that, visit The Boboli Gardens, a popular botanical garden that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazzale Michelangelo, an astonishing observation deck in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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 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 consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

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

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa and Lucca. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Let Piazza Del Duomo, Pisa set the tone for the day. Spend some time admiring this stunning public square before continuing your journey. Leaning Tower Of Pisa is your next stop. This world-famous monument is one of the best-rated sights in Florence.

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 Piazza Dell'anfiteatro. This stunning public square is a sight to behold. To round off your sightseeing experience, visit San Michele In Foro and Porta San Pietro. If time allows, end your day with Mura Di Lucca, a history-steeped historical landmark that offers a memorable conclusion to your exploration.

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.

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Unwind after your meal by stepping into Gosh*. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Quelo Bar, another top-rated bar in the area.

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

Your itinerary for day 7 of your road trip in Italy includes 1 stop and features some of the highlights of Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 2 nights.

Fortezza Medicea (siena) is must-visit monument and a great option for a daytime tour of the area. Continue your journey to Basilica Of San Domenico, a locally appreciated church, located just a leisurely stroll away. Next, head to Siena Cathedral, a visually striking 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 curiosity-inducing Pubblico Palace. If you’re looking for more, Piazza Del Campo is also a spectacular attraction that is worthwhile a visit. Lastly, don’t miss Tower Of Mangia, a place of respected interest in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

Enjoy a lovely dining experience at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Maudit Pub is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Impero Siena ensures a night out tailored to your taste.

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

On day 8 of your road trip, you’ll start and end your day in Siena, where you have 1 night left to stay.

Enjoy all that Antinori Nel Chianti Classico has to offer. This is a frequently visited winery you should not miss. Another must-see is Rocca Di Castellina In Chianti, a frequently visited castle in Siena.

When you’re ready for the next sight, head to Tumulo Di Montecalvario. From there, take a leisurely stroll to Fèlsina S. P. A. , another of the village’s up-and-coming attractions. We recommend continuing your self-guided tour at Castello Di Brolio, an enchanting place of interest in the village.

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.

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.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 9 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Santa Maria degli Angeli and Perugia are on today's agenda. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Start your day at Basilica Of San Francesco D'assisi. This UNESCO world heritage-listed church is an interesting place to see in Siena. Then, wander over to Piazza Del Comune. If history-steeped sites excite you, this public square will be right up your alley. Nearby, you’ll also find Rocca Maggiore. This culturally significant castle is a favorite among visitors.

Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Perugia Cathedral is a frequently visited spot in the town that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the awe-inspiring Piazza Iv Novembre. Take a moment to appreciate the fascinating details of this underrated public square. Wrap up your self-guided tour of Siena's top attractions with a visit to The Fontana Maggiore.

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

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

Have a fantastic dining experience at Ristorante Settimo Sigillo, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffè Baglioni offers an enticing alternative with its varied menu. Additionally, Bar Pellas is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Perugia.

After savoring a delicious meal, step into the vibrant nightlife at Tommi Bar, where the evening is just getting started. In the same way, Valentina offers a unique charm perfect for experiencing the local bar scene in Perugia. Caffe Dal Perugino 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 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including City of San Marino. When you’re not sightseeing, take time to relax at your chosen hotel in Trieste, where you’ll be staying for 1 night.

Your adventure in Perugia is only getting started when you visit State Museum Of San Marino, an often recommended local hot spot. Another notable attraction to explore is Liberty Square.

After soaking in the highlights of these sights, take some time to wander Perugia's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Del Santo. Guaita Tower is also worth visiting.

At the end of the day, you will drive to Trieste, 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 Trieste. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Rustiko, a top recommendation for dinner tonight. Or, for a change of pace, Caffè San Marco boasts a menu that's sure to impress. Also, be sure to check out Osteria Marise. Known as a local hotspot, it’s a great choice for tonight in Trieste.

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.

Savor another day of unforgettable experiences in Italy!