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 will explore Trieste and Miramare / Miramar, 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 2 nights.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Cattedrale Di San Giusto Martire. This increasingly popular 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 locally renowned 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 picture-perfect 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 captivating Miramare Castle, 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.

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.

Make sure to reserve a table at Bauer Hotel, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of L'Osteria Le Guglie, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corner Pub, a hidden gem nestled in Venice. 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 Al Parlamento, where the evening is just getting started. In the same way, The Caffe Rosso offers a unique charm perfect for experiencing the local bar scene in Venice. Adagio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day in Italy!

Day 3 of your road trip across Italy promises a magnificent time exploring Venice. You have 1 night left in Venice. Take the opportunity to experience more of the best attractions and activities in the city.

Immerse yourself in Venice’s rich culture with today's sightseeing itinerary. Start your journey at Bridge Of Sighs. This grand monument is sure to ignite your curiosity. Next, dive into the majestic features of Doge's Palace, a must-visit palace 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 St Mark's Basilica, a notable church. For a change of scene, check out Piazza San Marco, known for its history-steeped features. We also recommend visiting Rialto Bridge. This historical landmark is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Grand Canal, yet another frequently visited attraction 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.

As you explore more of Venice, 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.

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

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.

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 Bologna. 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 3 nights.

Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most underrated attractions included on the itinerary is Piazza Santo Stefano. This symbolic public square will help you start your sightseeing on top. Then, take a leisurely stroll to Two Towers and learn what makes this stunning monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the spectacular Piazza Maggiore. After exploring the public square, head to Fountain Of Neptune, Bologna. This worthwhile monument is a highlight in Venice. As your day continues, stop by Bologna Cathedral, known for its symbolic features. Lastly, don’t forget to check out the intriguing Palazzo Pallavicini. Enjoy exploring this incredible palace at your own pace.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

Day 5 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in Florence by discovering the best things there are to see and do in the city.

Florence is brimming with adventures. Today’s wonderful stops include a church, a palace, an art gallery, a historical landmark, a botanical garden, an observation deck and much more! Begin your sightseeing adventure at the locally renowned Basilica Of Santa Croce In Florence and allow yourself time to explore. Just a short distance away you'll find your next stop, Palazzo Vecchio, a romantic palace that draws visitors from far and near.

Continue your journey to Uffizi Gallery, one of the city’s most spectacular spots that you shouldn’t miss. Another great site to visit is the world-famous Ponte Vecchio. When you're finished at the historical landmark, The Boboli Gardens awaits your visit. This botanical garden is a visually striking highlight on today's itinerary. Last up is an observation deck - the impressive Piazzale Michelangelo.

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 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 dining experience at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

Wake up to day 6 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!

Discover a day packed with fun adventures, breathtaking views, and photo-friendly spots in Florence. Begin your sightseeing with Piazza Del Duomo, Pisa. This wondrous public square is one of the top attractions in the city. Proceed to Leaning Tower Of Pisa, 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 Dell'anfiteatro. This popular public square is a traveler-favorite. Not far away, you’ll find San Michele In Foro, another key site on your sightseeing itinerary. Porta San Pietro is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Mura Di Lucca and uncover why it's recognized as one of the city's most locally appreciated attractions.

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

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

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar 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 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Fortezza Medicea (siena). This historic monument is sure to ignite your curiosity. Next, dive into the stunning features of Basilica Of San Domenico, a must-visit church 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 Siena Cathedral, a well-known church. For a change of scene, check out Pubblico Palace, known for its culturally significant features. We also recommend visiting Piazza Del Campo. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Tower Of Mangia, yet another frequently visited attraction in Florence.

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.

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

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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 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 Bargino, Castellina in Chianti, Castelnuovo Berardenga, and San Regolo to the fullest today with this curated day itinerary!

Start by visiting Antinori Nel Chianti Classico, a prime spot to begin your journey. This eye-catching winery is sure to impress. Next on your list is Rocca Di Castellina In Chianti, another must-visit landmark and up-and-coming castle renowned for its respected features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Tumulo Di Montecalvario. This symbolic archeological site is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Fèlsina S. P. A. , a frequently visited winery. Nearby, you'll also find Castello Di Brolio, ready to add charm to your journey.

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.

Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Let the evening flow smoothly from dinner to drinks at Charlie Mixology Bar Di Aldinucci Riccardo, a top-rated bar in the area. For other recommendations, Bar Pinacoteca provides a perfect setting for rounding out your night with style and great drinks. Likewise, San Paolo Pub offers a memorable night with diverse drink options and excellent service.

Relax and recharge in preparation for another adventurous day 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 2 vibrant destinations - Santa Maria degli Angeli and Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Siena. Some of the town’s most loved attractions await! Basilica Of San Francesco D'assisi is the perfect place to start. This church is one of the most notable places to visit in Siena. Next, head to Piazza Del Comune, a locally appreciated public square, known for its romantic 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 Rocca Maggiore. This visually striking castle is a highly recommended experience. Nearby, you'll also find Perugia Cathedral and Piazza Iv Novembre. Visit these for an interesting touch to your journey. Finish the day with a visit to The Fontana Maggiore, a historic monument in Siena.

At the end of the day, you will drive to Perugia, 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 Perugia's most popular restaurants, and connect with friendly locals for an authentic adventure.

Treat yourself to a delicious dinner at Ristorante Settimo Sigillo, an excellent option for tonight's dining. Looking for something different? Caffè Baglioni offers a tantalizing alternative with its diverse menu. And don’t miss Bar Pellas. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

Unwind after your meal by stepping into Tommi Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Valentina offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffe Dal Perugino, another top-rated bar in the area.

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

On day 10 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 City of San Marino. In the evening, you’ll end up in Trieste, where you will stay for 1 night.

State Museum Of San Marino is must-visit museum and a great starting point for the day. Next, continue your journey to Liberty Square, an increasingly popular point of interest, located just a leisurely stroll away.

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.

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.

Savor the flavors at Rustiko, a top pick for dinner tonight. Alternatively, Caffè San Marco beckons with its unique menu offerings. Also, consider Osteria Marise. With its consistent customer satisfaction, it’s an excellent option for dining in Trieste tonight.

Extend your evening after a delightful meal by visiting Mast, which offers the perfect atmosphere for a night out. Moreover, Urbanis is another popular option for a drink or two. Likewise, Coktail Bar Trieste | La Preferita also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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