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

Get ready for an exciting day in Trieste. Today’s sightseeing agenda includes a castle, a pier, a public square, an archeological site, a church and much more! Begin your adventure at Miramare Castle. This is a captivating castle you should not miss. Another must-see is Molo Audace, an underrated pier in Trieste.

When you’re ready for the next sight, head to Piazza Unità D'italia. From there, take a leisurely stroll to Roman Theatre Of Trieste, another of the village’s curiosity-inducing attractions. We recommend continuing your self-guided tour at Cattedrale Di San Giusto Martire, a historic place of interest in the village. If time allows, add Civico Museo Del Castello Di San Giusto to your itinerary. This beloved castle offers the perfect finishing touch to your day in Trieste.

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

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.

Enjoy a delicious meal at Rustiko, a highly-rated dining destination in Trieste. If you're eager to try something different, consider Caffè San Marco, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria Marise. With a reputation for consistently satisfying customers, it’s an excellent 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.

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

On day 3 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 Venice. In the evening, you’ll end up in Venice, where you will stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Trieste, featuring fun adventures, romantic experiences, and breathtaking views. Start at Bridge Of Sighs, a notable monument in the city. Then, head to Doge's Palace and soak in the ambiance of this enchanting palace.

There are many interesting places to see in Trieste, and when you are ready for more, go to St Mark's Basilica. This is one of the city’s most popular enchanting spots of interest. After exploring the church, visit the wondrous Piazza San Marco. Not far away, you'll also find Teatro La Fenice. This opera house is a picture-perfect highlight in Trieste. Before wrapping up your self-guided sightseeing tour, head to Rialto Bridge, an iconic historical landmark in the city.

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.

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

Enjoy a lovely meal at Bauer Hotel, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, L'Osteria Le Guglie is another top choice with a popular menu. You could also check for a table at Corner Pub. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Venice tonight.

Keep the excitement of the evening going by visiting a bar or two. Al Parlamento is an excellent place to start. You could also check out The Caffe Rosso, offering a different kind of charm. A last recommendation for the day is Adagio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Day 4 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

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.

Brace yourself for today’s incredible lineup of attractions in Venice, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Santa Maria Della Salute, a curiosity-inducing church in the city. Then, head to Peggy Guggenheim Collection and soak in the ambiance of this respected art gallery.

There are many interesting places to see in Venice, and when you are ready for more, go to Gallerie Dell'accademia. This is one of the city’s most frequently visited heritage-rich spots of interest. After exploring the art gallery, visit the curiosity-inducing Santa Maria Gloriosa Dei Frari. Not far away, you'll also find Grand Canal. This street is a romantic highlight 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 dinnertime approaches, it's time to head out for a bite to eat in Venice. 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.

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.

Keep the excitement of the evening going by visiting a bar or two. Il Mercante is an excellent place to start. You could also check out The Irish Pub Venezia, offering a different kind of charm. A last recommendation for the day is Ai Stagneri. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Head back to your accommodation in Venice and get some rest in preparation for another magical day of your road trip in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Padua, Bologna, and Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 3 nights.

Savor the day by visiting some of the best places to see in Venice, including a church, a public square, a monument, an art gallery and much more! Start your adventure at The Basilica Of St. Anthony. This popular church is a must-visit for travelers looking for a unique holiday experience. Make your way to Prato Della Valle located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Two Towers. Its breathtaking features will captivate you. After the monument, continue your tour of the city with a visit to Piazza Maggiore. Visitors usually appreciate the history-steeped features of this public square. Next up is Galleria Dell'accademia, a highly recommended art gallery. For a change of pace, head to Cathedral Of Santa Maria Del Fiore. As one of the most famous attractions in Venice, this church is the perfect place to end your self-guided sightseeing tour.

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

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.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

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

Day 6 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.

Start by visiting Piazzale Michelangelo, a prime spot to begin your journey. This visually striking observation deck is sure to impress. Next on your list is Basilica Of Santa Croce In Florence, another must-visit landmark and interesting church renowned for its photogenic features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Della Signoria. This masterful public square is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Palazzo Vecchio, a captivating palace. Nearby, you'll also find Uffizi Gallery, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Ponte Vecchio and wrap up your day with its symbolic appeal.

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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

Greet day 7 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa.

Set out on a day brimming with fun adventures, breathtaking views, and picturesque spots. Start at the worthwhile Battistero Di San Giovanni, a grand church in Florence. Next, go to Piazza Del Duomo, Pisa.

After visiting Battistero Di San Giovanni and Piazza Del Duomo, Pisa, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Campo Santo. This breathtaking cemetery offers a unique experience. Pisa Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Leaning Tower Of Pisa, one of the most breathtaking places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Knights' Square.

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

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.

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly 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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Gosh* stands out as an excellent choice for a post-dinner cocktail. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers an ideal atmosphere to enjoy the pleasures of the night. Quelo Bar is also a great option that provides a perfect setting for a relaxing evening.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip 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 for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a church, a palace, a public square and much more! Begin your adventure at Fortezza Medicea (siena). This is a worthwhile monument you should not miss. Another must-see is Basilica Of San Domenico, an often recommended church in Florence.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Pubblico Palace, another of the city’s frequently visited attractions. We recommend continuing your self-guided tour at Piazza Del Campo, an UNESCO world heritage-listed place of interest in the city. If time allows, add Tower Of Mangia to your itinerary. This frequently visited monument offers the perfect finishing touch to your day in Florence.

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

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.

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

Savor another day of unforgettable experiences in Italy!

At the end of the day, you'll drive back to Siena, where you'll stay for 1 night more.

Start your day at Palazzo Salimbeni. This photogenic palace is a locally appreciated place to see in Siena. Then, wander over to Porta Romana. If picture-perfect sites excite you, this monument will be right up your alley. Nearby, you’ll also find Cipressi Di San Quirico D'orcia. This serene rock formation 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, Museo Della Mezzadria Senese is a curiosity-inducing spot in the city that will captivate you with its unique charm. When you’re done at the museum, don’t forget to check out the inviting Abbazia Di Monte Oliveto Maggiore. Take a moment to appreciate the fascinating details of this worthwhile monastery. Wrap up your self-guided tour of Siena's top attractions with a visit to 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.

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.

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

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Bologna and Verona, 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.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Porta Castiglione. This instagrammable monument is sure to ignite your curiosity. Next, dive into the eye-catching features of Porta Borsari, a must-visit historical landmark 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 Verona Arena, a globally renowned stadium. For a change of scene, check out Gran Guardia, known for its photogenic features.

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.

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

Dine in style at Caffè degli Specchi, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Istriano Of Giobi And Oxa boasts a menu that's sure to impress. Also, be sure to check out Chimera di Bacco. Known as a local hotspot, it’s a great choice for tonight in Trieste.

Extend your evening after a delightful meal by visiting "life" New Bar Torinese Snc, which offers the perfect atmosphere for a night out. Moreover, White Cafe is another popular option for a drink or two. Likewise, Café James Joyce also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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