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

On day 2 of your road trip, you’ll start and end your day in Trieste, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Miramare / Miramar and Trieste. You still have 1 night left in Trieste.

Savor the day by visiting some of the best places to see in Trieste, including a castle, a street, a public square, a museum and much more! Start your adventure at Miramare Castle. This notable castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Canale Ponterosso Trieste located in Trieste for another exciting encounter.

Next, immerse yourself in the setting of Piazza Unità D'italia. Its history-steeped features will captivate you. After the public square, continue your tour of the village with a visit to Revoltella Museum. Visitors usually appreciate the visually striking features of this museum.

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.

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.

Let the evening flow smoothly from dinner to drinks at Mast, a top-rated bar in the area. For other recommendations, Urbanis provides a perfect setting for rounding out your night with style and great drinks. Likewise, Coktail Bar Trieste | La Preferita offers a memorable night with diverse drink options and excellent service.

Raise your glass and celebrate another amazing day of your road trip 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.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming city of Trieste. Your adventure starts at Bridge Of Sighs, a popular local hot spot. Another notable attraction to explore is Doge's Palace. This notable palace is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Trieste's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to St Mark's Basilica. This grand church offers a fascinating experience that many visitors find memorable. Piazza San Marco is also worth visiting, along with Grand Canal. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Rialto Bridge. This iconic historical landmark provides a fitting finale to your sightseeing.

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.

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

Treat yourself to a delightful dinner at Bauer Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try L'Osteria Le Guglie? It's another excellent option with a diverse menu. Consider reserving a table at Corner Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

Explore the vibrant nightlife at Al Parlamento after your meal, a hub for lively evenings and memorable moments. Or, head to The Caffe Rosso for a great selection of flavorful drinks and a charming setting. Furthermore, Adagio is perfect for those looking to extend their night with a touch of local flavor.

Say good night to Venice and look forward to another great day of your road trip 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 family-friendly attractions, photo-friendly spots, and history-rich sites. Start at the interesting 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 awe-inspiring 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 enchanting 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.

As you explore more of Florence, 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 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 gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

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

On day 5 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Begin your adventure at Battistero Di San Giovanni. This is an increasingly popular 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 intriguing attractions. If time allows, add Leaning Tower Of Pisa to your itinerary. This wondrous monument offers the perfect finishing touch to your day in Florence.

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

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

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Head back to your accommodation in Florence and get some rest in preparation for another magical 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, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in San Gimignano, where you’ll be staying for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Siena Cathedral. This well-known church provides an insightful glimpse into the city's identity. Next, discover Piazza Del Campo, a history-steeped public square, promising a delightful encounter.

Continue your sightseeing with a visit to Tower Of Mangia, an often recommended monument. When you’re done, don’t forget to make a stop at the locally appreciated Porta San Giovanni.

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.

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

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.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore San Gimignano on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Del Duomo is the first of them. Spend some time admiring this inviting public square before continuing your journey. Palazzo Comunale, Pinacoteca, Torre Grossa is your next stop. This worthwhile museum is one of the best-rated sights in San Gimignano.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Sangimignano1300. This history-steeped museum is a sight to behold.

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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in San Gimignano. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Relax and recharge in preparation for another adventurous day 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 Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Trieste, which will be your home away from home for 1 night.

Start by visiting Two Towers, a prime spot to begin your journey. This historic monument is sure to impress. Next on your list is Piazza Maggiore, another must-visit landmark and famous public square renowned for its romantic features.

While exploring and sightseeing, take time to savor the culture of San Gimignano by sampling some local delicacies. When you’re ready for more sightseeing, head to Biblioteca Salaborsa. This heritage-rich library is an essential place to visit for anyone looking for the full San Gimignano experience. We also recommend visiting Bologna Cathedral, a locally appreciated church.

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.

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 lovely dining experience at Caffè degli Specchi, a popular restaurant in Trieste. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Trieste at Osteria Istriano Of Giobi And Oxa, 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 Chimera di Bacco. It’s yet another ideal choice to enhance your time in Trieste tonight.

To truly maximize your evening out, consider visiting "life" New Bar Torinese Snc after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to White Cafe, another bar with an inviting ambiance. Similarly, Café James Joyce also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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