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

On day 2 of your road trip, you’ll start and end your day in 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 locally renowned 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 romantic 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 historic 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 intriguing 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.

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.

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

Unwind after your meal by stepping into Mast. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Urbanis offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Coktail Bar Trieste | La Preferita, another top-rated bar in the area.

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

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Venice, 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.

Today, you'll explore some of the most beautiful places in Trieste, including a monument, a palace, a church, a public square, an opera house, a historical landmark and much more! Start your day with a visit to Bridge Of Sighs. This interesting monument is a must-visit in the city. When you’re ready for your next discovery, continue to Doge's Palace, which may be one of the most romantic places you will experience today.

One of the best things about exploring Trieste on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to St Mark's Basilica, a locally renowned church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza San Marco and Teatro La Fenice. End your day with a visit to Rialto Bridge, a globally renowned historical landmark that’s sure to leave a lasting impression.

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 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.

Enjoy a lovely dining experience at Bauer Hotel, a popular restaurant in Venice. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Venice at L'Osteria Le Guglie, 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 Corner Pub. It’s yet another ideal choice to enhance your time in Venice tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Al Parlamento stands out as an excellent choice for a post-dinner cocktail. Alternatively, The Caffe Rosso offers an ideal atmosphere to enjoy the pleasures of the night. Adagio 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!

On day 4 of your road trip, you will have an entire day to explore Venice. You’ll stay in Venice for 1 night and discover all the best things to see and do in the area.

A visit to Cannaregio in Venice is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Today’s itinerary in Venice covers several incredible sights, including a church, an art gallery, and a street. Start your adventure at Santa Maria Della Salute. This worthwhile church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Peggy Guggenheim Collection, a must-see art gallery 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 Gallerie Dell'accademia. This often recommended art gallery offers an enriching experience. For a change of pace, head to Santa Maria Gloriosa Dei Frari, where you can take in culturally significant features. Conclude your self-guided sightseeing tour with a visit to 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 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.

Continue your evening by exploring the vibrant nightlife scene at Il Mercante, a prime destination for a thrilling night out. Also, don’t forget to check out The Irish Pub Venezia, a bar that offers unique local touches. Likewise, Ai Stagneri provides an excellent alternative for a fun evening.

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 3 vibrant destinations - Padua, Bologna, and Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 3 nights here for some well-deserved relaxation.

Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most locally renowned attractions included on the itinerary is The Basilica Of St. Anthony. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Prato Della Valle and learn what makes this visually striking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the interesting Two Towers. After exploring the monument, head to Piazza Maggiore. This impressive public square is a highlight in Venice. As your day continues, stop by Galleria Dell'accademia, known for its heritage-rich features. Lastly, don’t forget to check out the top-rated Cathedral Of Santa Maria Del Fiore. Enjoy exploring this incredible church at your own pace.

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

Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

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

Day 6 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and breathtaking views. Start at Piazzale Michelangelo, a widely recognized observation deck in the city. Then, head to Basilica Of Santa Croce In Florence and soak in the ambiance of this culturally significant church.

There are many interesting places to see in Florence, and when you are ready for more, go to Piazza Della Signoria. This is one of the city’s most spectacular grand spots of interest. After exploring the public square, visit the captivating Palazzo Vecchio. Not far away, you'll also find Uffizi Gallery. This art gallery is a historic highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Ponte Vecchio, a world-famous historical landmark in the city.

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.

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.

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

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a cemetery, a monument and much more! Start your adventure at Battistero Di San Giovanni. This underrated church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the breathtaking wonders of Piazza Del Duomo, Pisa, 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 Campo Santo. This intriguing cemetery offers an enriching experience. For a change of pace, head to Pisa Cathedral, where you can take in historic features. Conclude your self-guided sightseeing tour with a visit to Leaning Tower Of Pisa and Knights' Square. These sights offer a fulfilling end to a perfect day.

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.

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.

Following your dinner, dive into the local bar culture at Gosh*. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Antico Caffè Del Moro - Art Bar Firenze, the perfect place for those looking to experience the best of the nightlife. Similarly, Quelo Bar 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!

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Get ready to discover some of the most iconic wonders in Florence, including a monument, a church, a palace, a public square and much more! Start your day at Fortezza Medicea (siena). This historic monument is an often recommended place to see in Florence. Then, wander over to Basilica Of San Domenico. If picture-perfect sites excite you, this church will be right up your alley. Nearby, you’ll also find Siena Cathedral. This grand church 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, Pubblico Palace is an intriguing spot in the city that will captivate you with its unique charm. When you’re done at the palace, don’t forget to check out the respected Piazza Del Campo. Take a moment to appreciate the fascinating details of this impressive public square. Wrap up your self-guided tour of Florence's top attractions with a visit to Tower Of Mangia.

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.

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

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

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

On day 9 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 Siena, San Quirico d'Orcia, Buonconvento, Monte Oliveto Maggiore, and Asciano to the fullest today with this curated day itinerary!

Just a short distance away you'll find your next stop, Porta Romana, a breathtaking monument that draws visitors from far and near.

Continue your journey to Cipressi Di San Quirico D'orcia, one of the city’s most curiosity-inducing spots that you shouldn’t miss. Another great site to visit is the frequently visited Museo Della Mezzadria Senese. When you're finished at the museum, Abbazia Di Monte Oliveto Maggiore awaits your visit. This monastery is an inviting highlight on today's itinerary. Last up is a point of interest - the intriguing Crete Senesi Vista.

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

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.

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.

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Pinacoteca is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, San Paolo Pub ensures a night out tailored to your taste.

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 2 destinations, Bologna and Verona. When you’re not sightseeing, take time to relax at your selected hotel in Trieste, where you’ll be staying for 1 night.

Siena is home to plenty of attractions that offer fun adventures, picturesque spots, and history-rich sites! Start at Porta Castiglione, an increasingly popular monument that is worthwhile a visit in the city. Nearby, you’ll find Porta Borsari, enchanting visitors with its photogenic appeal. Continue your exploration at Verona Arena. This stadium is one of the city’s most timeless 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 Gran Guardia.

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.

Make sure to reserve a table at Caffè degli Specchi, an iconic dining spot in Trieste. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Istriano Of Giobi And Oxa, a popular restaurant in Trieste. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Chimera di Bacco, a hidden gem nestled in Trieste. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Round off your dining experience by visiting "life" New Bar Torinese Snc, a prime location for a drink. Alternatively, explore the distinctive characteristics of White Cafe, a bar catering to every mood and preference. Café James Joyce likewise offers a unique atmosphere, perfect for a memorable night out.

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