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.

Start by visiting Miramare Castle, a prime spot to begin your journey. This romantic castle is sure to impress. Next on your list is Canale Ponterosso Trieste, another must-visit landmark and increasingly popular street renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of Trieste by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Unità D'italia. This history-steeped public square is an essential place to visit for anyone looking for the full Trieste experience. We also recommend visiting Revoltella Museum, an often recommended 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 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.

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

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.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Bridge Of Sighs. This captivating monument is a majestic place to see in Trieste. Continue your discovery at Doge's Palace, an UNESCO world heritage-listed palace with stories to tell.

As you stroll around Trieste, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to St Mark's Basilica. This well-known church offers a romantic encounter with Trieste. Next, make your way to Piazza San Marco to add another highlight to your day. After that, visit Grand Canal, an up-and-coming street that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Rialto Bridge, a globally renowned historical landmark in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this 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 day of adventure, treat yourself to an exquisite dinner at one of Venice's best restaurants.

Savor the flavors at Bauer Hotel, a top pick for dinner tonight. Alternatively, L'Osteria Le Guglie beckons with its unique menu offerings. Also, consider Corner Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Al Parlamento stands out as an excellent choice for a post-dinner cocktail. Alternatively, The Caffe Rosso offers an ideal atmosphere to enjoy the pleasures of the night. Adagio is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Today’s agenda in Venice includes a church, an art gallery, a historical landmark, a public square, a palace and much more! Basilica Of Santa Croce In Florence is must-visit church and a great starting point for the day. Next, continue your journey to Uffizi Gallery, an impressive art gallery, located just a leisurely stroll away. Next, head to Ponte Vecchio, a history-steeped historical landmark, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Venice. When you're ready, let your sightseeing route take you to the curiosity-inducing Loggia Dei Lanzi. If you’re looking for more, Palazzo Vecchio is also a popular attraction that is worthwhile a visit. Lastly, don’t miss Piazza Della Signoria, a place of history-steeped interest in the city.

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.

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

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice 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.

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

A blend of family-friendly attractions, breathtaking views, and picturesque spots await you in Florence on today’s itinerary. First up is the increasingly popular church, Battistero Di San Giovanni. Afterward, continue to Piazza Del Duomo, Pisa, a public square every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Campo Santo. This up-and-coming cemetery is an essential stop. Following that, head to Pisa Cathedral, another must-visit site that will enhance your experience. Don’t forget to stop by Angelo Caduto, a curiosity-inducing sightseeing destination in the city. Finally, end your day with a visit to Leaning Tower Of Pisa, an UNESCO world heritage-listed monument that offers the perfect conclusion to your sightseeing of the day.

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

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.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Florence is brimming with adventures. Today’s wonderful stops include a church, a public square, and a monument. Begin your sightseeing adventure at the locally renowned Siena Cathedral and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Del Campo, an enchanting public square that draws visitors from far and near.

Continue your journey to Tower Of Mangia, one of the city’s most locally appreciated spots that you shouldn’t miss. Another great site to visit is the up-and-coming 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.

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.

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

Start by visiting Piazza Del Duomo, a prime spot to begin your journey. This majestic public square is sure to impress. Next on your list is Palazzo Comunale, Pinacoteca, Torre Grossa, another must-visit landmark and increasingly popular museum renowned for its culturally significant 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 Sangimignano1300. This heritage-rich museum is an essential place to visit for anyone looking for the full San Gimignano 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.

Take some time to reflect on your day and savor another beautiful night 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 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Trieste. You will spend 1 night here for some well-deserved relaxation.

Get ready for an exciting day in San Gimignano. Today’s sightseeing agenda includes a monument, a public square, a library, a church and much more! Begin your adventure at Two Towers. This is a captivating monument you should not miss. Another must-see is Piazza Maggiore, a spectacular public square in San Gimignano.

When you’re ready for the next sight, head to Biblioteca Salaborsa. From there, take a leisurely stroll to Bologna Cathedral, another of the city’s frequently visited attractions.

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.

Have a fantastic dining experience at Caffè degli Specchi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria Istriano Of Giobi And Oxa offers an enticing alternative with its varied menu. Additionally, Chimera di Bacco is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Trieste.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at "life" New Bar Torinese Snc, a well-loved spot among locals and tourists. Or, head to White Cafe. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Café James Joyce, another top-rated place in the area.

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