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

Greet day 2 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Trieste 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 Miramare / Miramar and Trieste.

Get ready to discover some of the most iconic wonders in Trieste, including a castle, a street, a public square, a museum and much more! Start your day at Miramare Castle. This romantic castle is a captivating place to see in Trieste. Then, wander over to Canale Ponterosso Trieste. If romantic sites excite you, this street will be right up your alley. Nearby, you’ll also find Piazza Unità D'italia. This visually striking public square is a favorite among visitors.

Trieste offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Revoltella Museum is an intriguing spot in the village that will captivate you with its unique charm.

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.

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.

Continue your lively evening at Mast, a perfect place for winding down or revving up the night, depending on which mood you’re in. Urbanis is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Coktail Bar Trieste | La Preferita ensures a night out tailored to your taste.

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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Venice. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Venice. You will spend 1 night here for some well-deserved relaxation.

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

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 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.

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.

Extend your evening after a delightful meal by visiting Al Parlamento, which offers the perfect atmosphere for a night out. Moreover, The Caffe Rosso is another popular option for a drink or two. Likewise, Adagio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Florence, 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 Florence. You’ll stay here for 2 nights.

Set out on a day brimming with fun adventures, picturesque spots, and historic treasures. Start at the well-known Basilica Of Santa Croce In Florence, a photogenic church in Venice. Next, go to Uffizi Gallery.

After visiting Basilica Of Santa Croce In Florence and Uffizi Gallery, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to Ponte Vecchio. This visually striking historical landmark offers a unique experience. Loggia Dei Lanzi is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Palazzo Vecchio, one of the most history-steeped places to visit in Venice. If you still have some time left for sightseeing, we also recommend stopping by Piazza Della Signoria.

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 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.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

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

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

Begin your adventure at Battistero Di San Giovanni. This is an often recommended church you should not miss. Another must-see is Piazza Del Duomo, Pisa, an iconic public square in Florence.

When you’re ready for the next sight, head to Campo Santo. From there, take a leisurely stroll to Pisa Cathedral, another of the city’s increasingly popular attractions. If time allows, add Leaning Tower Of Pisa to your itinerary. This world-famous monument offers the perfect finishing touch to your day in Florence.

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.

Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in San Gimignano, which will be your home away from home 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 widely recognized public square, located just a leisurely stroll away. Next, head to Tower Of Mangia, an UNESCO world heritage-listed 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.

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 and reflect on the day's adventures.

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

Day 7 offers a multitude of experiences. You will stay in San Gimignano for 1 night more, offering you enough time to explore at a relaxed pace.

Brace yourself for today’s incredible lineup of attractions in San Gimignano, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Piazza Del Duomo, an intriguing public square in the village. Then, head to Palazzo Comunale, Pinacoteca, Torre Grossa and soak in the ambiance of this UNESCO world heritage-listed museum.

There are many interesting places to see in San Gimignano, and when you are ready for more, go to Sangimignano1300. This is one of the village’s most locally appreciated photogenic spots of interest.

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 San Gimignano, 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.

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.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Two Towers. This well-known monument is a breathtaking place to see in San Gimignano. Continue your discovery at Piazza Maggiore, a history-steeped public square with stories to tell.

As you stroll around San Gimignano, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Biblioteca Salaborsa. This up-and-coming library offers an instagrammable encounter with San Gimignano. Next, make your way to Bologna Cathedral to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in San Gimignano.

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 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.

Enjoy a delicious meal at Caffè degli Specchi, a highly-rated dining destination in Trieste. If you're eager to try something different, consider Osteria Istriano Of Giobi And Oxa, another top spot with a tantalizing menu. You might also want to secure a reservation at Chimera di Bacco. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Trieste this evening.

Keep the excitement of the evening going by visiting a bar or two. "life" New Bar Torinese Snc is an excellent place to start. You could also check out White Cafe, offering a different kind of charm. A last recommendation for the day is Café James Joyce. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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