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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Trieste and Miramare / Miramar. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Venice. You will spend 2 nights here for some well-deserved relaxation.

Immerse yourself in Trieste’s rich culture with today's sightseeing itinerary. Start your journey at Cattedrale Di San Giusto Martire. This picture-perfect church is sure to ignite your curiosity. Next, dive into the culturally significant features of Roman Theatre Of Trieste, a must-visit archeological site 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 Piazza Unità D'italia, a notable public square. For a change of scene, check out Piazza Della Borsa, known for its romantic features. We also recommend visiting Canale Ponterosso Trieste. This street is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Miramare Castle, yet another notable attraction in Trieste.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

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.

Treat yourself to a delicious dinner at Bauer Hotel, an excellent option for tonight's dining. Looking for something different? L'Osteria Le Guglie offers a tantalizing alternative with its diverse menu. And don’t miss Corner Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

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

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

Day 3 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Venice covers several incredible sights, including a monument, a palace, a church, a public square, a historical landmark, a street and much more! Start your adventure at Bridge Of Sighs. This interesting monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Doge's Palace, a must-see palace 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 St Mark's Basilica. This locally renowned church offers an enriching experience. For a change of pace, head to Piazza San Marco, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Rialto Bridge and Grand Canal. These sights offer a fulfilling end to a perfect day.

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 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.

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.

To truly maximize your evening out, consider visiting Il Mercante after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to The Irish Pub Venezia, another bar with an inviting ambiance. Similarly, Ai Stagneri also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Piazza Santo Stefano. This up-and-coming public square is a romantic place to see in Venice. Continue your discovery at Two Towers, a culturally significant monument with stories to tell.

As you stroll around Venice, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Maggiore. This extraordinary public square offers a visually striking encounter with Venice. Next, make your way to Fountain Of Neptune, Bologna to add another highlight to your day. After that, visit Bologna Cathedral, a beloved church that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Palazzo Pallavicini, a locally appreciated palace 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 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.

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.

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.

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.

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

Get ready for a day filled with fun adventures, picturesque spots, and history-rich sites in the charming city of Florence. Your adventure starts at Basilica Of Santa Croce In Florence, a notable local hot spot. Another notable attraction to explore is Palazzo Vecchio. This notable palace is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Uffizi Gallery. This historic art gallery offers a fascinating experience that many visitors find memorable. Ponte Vecchio is also worth visiting, along with The Boboli Gardens. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazzale Michelangelo. This widely recognized observation deck provides a fitting finale to your sightseeing.

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 Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

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.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 1 night more, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary!

Today’s agenda in Florence includes a public square, a monument, a church, a historical landmark and much more! Piazza Del Duomo, Pisa is must-visit public square and a great starting point for the day. Next, continue your journey to Leaning Tower Of Pisa, a world-famous monument, located just a leisurely stroll away. Next, head to Piazza Dell'anfiteatro, a history-steeped public square, 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 intriguing San Michele In Foro. If you’re looking for more, Porta San Pietro is also an intriguing attraction that is worthwhile a visit. Lastly, don’t miss Mura Di Lucca, a place of enchanting interest in the city.

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

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.

Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

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

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Fortezza Medicea (siena) is the perfect place to start. This monument is one of the most curiosity-inducing places to visit in Florence. Next, head to Basilica Of San Domenico, a frequently visited church, known for its picture-perfect 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 Siena Cathedral. This grand church is a highly recommended experience. Nearby, you'll also find Pubblico Palace and Piazza Del Campo. Visit these for an interesting touch to your journey. Finish the day with a visit to Tower Of Mangia, a breathtaking monument in Florence.

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.

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most worthwhile attractions included on the itinerary is Antinori Nel Chianti Classico. This stunning winery will help you start your sightseeing on top. Then, take a leisurely stroll to Rocca Di Castellina In Chianti and learn what makes this visually striking castle unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Tumulo Di Montecalvario. After exploring the archeological site, head to Fèlsina S. P. A. This intriguing winery is a highlight in Siena. As your day continues, stop by Castello Di Brolio, known for its enchanting features.

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

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

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.

Unwind after your meal by stepping into Charlie Mixology Bar Di Aldinucci Riccardo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Pinacoteca offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook San Paolo Pub, another top-rated bar in the area.

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

On day 9 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 Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a church, a public square, a castle, a monument and much more! Begin your adventure at Basilica Of San Francesco D'assisi. This is an interesting church you should not miss. Another must-see is Piazza Del Comune, a worthwhile public square in Siena.

When you’re ready for the next sight, head to Rocca Maggiore. From there, take a leisurely stroll to Perugia Cathedral, another of the town’s worthwhile attractions. We recommend continuing your self-guided tour at Piazza Iv Novembre, a romantic place of interest in the town. If time allows, add The Fontana Maggiore to your itinerary. This often recommended monument offers the perfect finishing touch to your day in Siena.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

As you explore more of Perugia, 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 Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Tommi Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Valentina for a great selection of flavorful drinks and a charming setting. Furthermore, Caffe Dal Perugino is perfect for those looking to extend their night with a touch of local flavor.

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

Dive into day 10 of your remarkable road trip in Italy. Today you will explore City of San Marino, 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 Trieste. You’ll stay here for 1 night.

Start your adventure at State Museum Of San Marino. This underrated museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Liberty Square located in Perugia for another exciting encounter.

Next, immerse yourself in the setting of Basilica Del Santo. After the church, continue your tour of the city with a visit to Guaita Tower.

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.

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.

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.

After enjoying a fulfilling meal, continue your evening at Mast, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Urbanis offers a welcoming atmosphere for easing into the nightlife. Similarly, Coktail Bar Trieste | La Preferita provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!