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 still have 1 night to spend in Trieste, there’s no need to rush. Experience Miramare / Miramar and Trieste to the fullest today with this curated day itinerary.

Enjoy all that Canale Ponterosso Trieste has to offer. This is an underrated street you should not miss. Another must-see is Piazza Unità D'italia, a locally renowned public square in Trieste.

When you’re ready for the next sight, head to Revoltella Museum.

When you’re ready to jump back into the car and say goodbye to Trieste, you’ll hit the road in the direction of Miramare / Miramar. This drive usually takes around 18 min.

Miramare Castle is a popular castle we recommend visiting today. Discover its enchanting features before continuing your self-guided tour.

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

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.

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 your delicious meal, get a taste of the vibrant nightlife with a visit to Mast, known for its inviting atmosphere. Urbanis is another great option if you’re looking for a place to get the night started. Similarly, Coktail Bar Trieste | La Preferita provides a great setting to enjoy the night away.

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

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of Venice. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 1 night.

Venice’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Trieste behind. This drive usually takes around 2 hours 17 min. Venice welcomes you with a multitude of unique vacation experiences.

Spend your afternoon discovering Bridge Of Sighs, a notable monument known for its history-steeped features. Next, continue your sightseeing at Doge's Palace, a locally renowned palace.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by St Mark's Basilica and uncover the details of this inviting church. Make sure to also explore Piazza San Marco, a wondrous public square. For your last stop, consider Grand Canal, an enchanting street that many travelers find worth the detour.

When you’re done exploring for the day, you’ll drive to your hotel in Venice. Check in and relax before you head out to tour the city.

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

Enjoy a delicious meal at Bauer Hotel, a highly-rated dining destination in Venice. If you're eager to try something different, consider L'Osteria Le Guglie, another top spot with a tantalizing menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

After your meal, keep the night alive at a bar like Al Parlamento, known for its lively atmosphere. The Caffe Rosso is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Adagio offers an excellent atmosphere for those looking to amp up the evening.

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

On day 4 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Continue your road trip and head to your next destination, Florence. This car ride takes around 2 hours 56 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Basilica Of Santa Croce In Florence, an interesting church that everyone visiting Florence should see. Next, head to Uffizi Gallery. This standout art gallery is one of the most spectacular attractions in the region.

If you're keen to see more, don’t miss out on Ponte Vecchio, a history-steeped historical landmark popular among locals as well as travelers. Loggia Dei Lanzi is an excellent attraction to visit next. Spend some time learning more about this up-and-coming public square before you continue your journey. Lastly, visit Palazzo Vecchio, a culturally significant palace and a top attraction in the city.

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 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 meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Fasten your seatbelt and make your way to your next stop — Pisa, home to many well-known sights in the region. Keep in mind that your travel time from Florence to Pisa may take around 1 hour 14 min without traffic disruptions. Upon arrival in Pisa, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Battistero Di San Giovanni. Spend some time admiring the culturally significant features of the church before you continue to your next stop. Then, head to Piazza Del Duomo, Pisa. This iconic public square is a traveler-favorite in the city.

If you're keen to see more, continue to Campo Santo. Feed your curiosity by learning something new about the cemetery. Next, take your journey to Pisa Cathedral, an up-and-coming church.

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

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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 culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Siena and San Gimignano. When you’re not sightseeing, take time to relax at your chosen hotel in San Gimignano, where you’ll be staying for 2 nights.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Siena. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 12 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Siena Cathedral is a popular church we recommend visiting today. Discover its enchanting features before continuing your self-guided tour to Piazza Del Campo, a romantic public square that’s well-regarded in the area.

Next, stop by Tower Of Mangia, a picture-perfect monument.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Gimignano may take around 46 min. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Savor the day by heading to Porta San Giovanni, a worthwhile monument that draws visitors from near and far.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in San Gimignano. San Gimignano 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 San Gimignano's most popular restaurants, and connect with friendly locals for a true cultural experience.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Day 7 of your road trip will take you to the best attractions San Gimignano has to offer. Cherish the 1 night you have left in the village and use the provided itinerary to discover what to see in San Gimignano.

San Gimignano is brimming with adventures.

Start your day at Piazza Del Duomo. This UNESCO world heritage-listed public square is an up-and-coming place to see in San Gimignano. Then, wander over to Palazzo Comunale, Pinacoteca, Torre Grossa. If historic sites excite you, this museum will be right up your alley. Nearby, you’ll also find Sangimignano1300. This eye-catching museum is a favorite among visitors.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine.

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Trieste, where will spend 1 night.

Set your GPS to Bologna and hit the road. Expect a journey of approximately 2 hours without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bologna beckons with new experiences!

One of our top recommendations for your sightseeing is Two Towers. Spend some time admiring the picture-perfect features of the monument before you continue to your next stop. Then, head to Piazza Maggiore. This impressive public square is a traveler-favorite in the city.

If you're keen to see more, continue to Biblioteca Salaborsa. Feed your curiosity by learning something new about the library. Next, take your journey to Bologna Cathedral, an up-and-coming church.

When you’re done exploring for the day, you’ll drive to your hotel in Trieste. Check in and relax before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Trieste, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Caffè degli Specchi, a top-rated dining spot in Trieste. If you're in the mood for something new, try Osteria Istriano Of Giobi And Oxa, another premier location with a delectable menu. You might also want to book a table at Chimera di Bacco. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Trieste.

After your delicious meal, get a taste of the vibrant nightlife with a visit to "life" New Bar Torinese Snc, known for its inviting atmosphere. White Cafe is another great option if you’re looking for a place to get the night started. Similarly, Café James Joyce provides a great setting to enjoy the night away.

Relax and look forward to more memorable moments to come!