9-Day Italy Self-Drive Road Trip With Itinerary from Trieste to Venice, Florence, and San Gimignano

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!

Trieste is brimming with adventures. Today’s wonderful stops include a castle, a street, a public square, a museum and much more! Begin your sightseeing adventure at the popular Miramare Castle and allow yourself time to explore. Just a short distance away you'll find your next stop, Canale Ponterosso Trieste, a romantic street that draws visitors from far and near.

Continue your journey to Piazza Unità D'italia, one of the village’s most notable spots that you shouldn’t miss. Another great site to visit is the up-and-coming Revoltella Museum.

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

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

Enjoy a lovely meal at Rustiko, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè San Marco is another top choice with a popular menu. You could also check for a table at Osteria Marise. As an establishment that gains consistently high praises from customers, it’s an ideal choice 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.

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

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 1 night.

Get ready for an exciting day in Trieste. Today’s sightseeing agenda includes a monument, a palace, a church, a public square, a street, a historical landmark and much more! Begin your adventure at Bridge Of Sighs. This is a locally renowned monument you should not miss. Another must-see is Doge's Palace, a well-known palace in Trieste.

When you’re ready for the next sight, head to St Mark's Basilica. From there, take a leisurely stroll to Piazza San Marco, another of the city’s wondrous attractions. We recommend continuing your self-guided tour at Grand Canal, an UNESCO world heritage-listed place of interest in the city. If time allows, add Rialto Bridge to your itinerary. This globally renowned historical landmark offers the perfect finishing touch to your day in Trieste.

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.

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.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Caffe Rosso, a bar catering to every mood and preference. Adagio likewise offers a unique atmosphere, perfect for a memorable night out.

Celebrate another amazing day of your road trip adventure 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 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Venice. Some of the city’s most loved attractions await! Basilica Of Santa Croce In Florence is the perfect place to start. This church is one of the most captivating places to visit in Venice. Next, head to Uffizi Gallery, a spectacular art gallery, known for its instagrammable 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 Ponte Vecchio. This symbolic historical landmark is a highly recommended experience. Nearby, you'll also find Loggia Dei Lanzi and Palazzo Vecchio. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Della Signoria, an enchanting public square in Venice.

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.

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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.

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

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

Start your adventure at Battistero Di San Giovanni. This underrated church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Duomo, Pisa located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Campo Santo. Its historic features will captivate you. After the cemetery, continue your tour of the city with a visit to Pisa Cathedral. Visitors usually appreciate the breathtaking features of this church. Next up is Angelo Caduto, a highly recommended sightseeing destination. For a change of pace, head to Leaning Tower Of Pisa. As one of the most timeless attractions in Florence, this monument 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 Florence.

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

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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 6 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 Siena and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 2 nights.

Today’s agenda in Florence includes a church, a public square, and a monument. Siena Cathedral is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Del Campo, a spectacular public square, located just a leisurely stroll away. Next, head to Tower Of Mangia, a culturally significant monument, also available for your discovery today.

At the end of the day, you will drive to San Gimignano, 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 San Gimignano's best restaurants.

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

Day 7 of your road trip across Italy promises a magnificent time exploring San Gimignano. You have 1 night left in San Gimignano. Take the opportunity to experience more of the best attractions and activities in the village.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the up-and-coming Piazza Del Duomo, an UNESCO world heritage-designated public square in San Gimignano. Next, go to Palazzo Comunale, Pinacoteca, Torre Grossa.

After visiting Piazza Del Duomo and Palazzo Comunale, Pinacoteca, Torre Grossa, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Sangimignano1300. This history-steeped museum offers a unique experience.

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 San Gimignano. If you are looking to dine at a popular restaurant in the village, it's often a good idea to reserve a table in advance.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Trieste, where you’ll be staying for 1 night.

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the captivating Two Towers, an instagrammable monument in San Gimignano. Next, go to Piazza Maggiore.

After visiting Two Towers and Piazza Maggiore, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Biblioteca Salaborsa. This instagrammable library offers a unique experience. Bologna Cathedral is another noteworthy attraction worthwhile a visit.

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 explore more of Trieste, 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.

Savor the flavors at Caffè degli Specchi, a top pick for dinner tonight. Alternatively, Osteria Istriano Of Giobi And Oxa beckons with its unique menu offerings. Also, consider Chimera di Bacco. With its consistent customer satisfaction, it’s an excellent option for dining in Trieste tonight.

Keep the evening going at "life" New Bar Torinese Snc, a great choice for enjoying the after-dinner hours with a drink. You could also go to White Cafe, which offers a similarly pleasant setting and great drinks. Another option is Café James Joyce, which provides an inviting environment for unwinding after a busy day out.

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