Two-Week Italy Self-Drive Road Trip With Itinerary from Trieste traveling west to Venice, Florence, Rome, and Siena

On day 2 of your road trip, you will have an entire day to explore Borgo Grotta Gigante / Briščiki. You’ll stay in Trieste for 1 night and discover all the best things to see and do in the area.

Bring your curiosity for today’s adventure around Trieste. Some of the village’s most loved attractions await! Grotta Gigante is the perfect place to start. This cave is one of the most beloved places to visit in Trieste. Next, head to Canale Ponterosso Trieste, an often recommended street, known for its visually striking 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 Molo Audace. This history-steeped pier is a highly recommended experience. Nearby, you'll also find Piazza Unità D'italia and Revoltella Museum. Visit these for an interesting touch to your journey. Finish the day with a visit to Miramare Castle, a visually striking castle in Trieste.

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 Trieste. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

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.

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

On day 3 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 Venice. In the evening, you’ll end up in Venice, where you will stay for 2 nights.

Today's adventure in Trieste promises more breathtaking discoveries and enriching experiences! Begin at Bridge Of Sighs. This visually striking monument is a highlight of any visit in the city. Then, enjoy Doge's Palace, another romantic attraction that never fails to captivate visitors. Next, head over to St Mark's Basilica, one of the city’s most notable attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of St Mark's Campanile. This romantic monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza San Marco, a timeless public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Rialto Bridge before you head back to your hotel.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Venice. Venice 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 Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Bauer Hotel, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of L'Osteria Le Guglie, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corner Pub, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Al Parlamento, known for its inviting atmosphere. The Caffe Rosso is another great option if you’re looking for a place to get the night started. Similarly, Adagio provides a great setting to enjoy the night away.

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

Day 4 of your road trip will take you to the best attractions Venice has to offer. Cherish the 1 night you have left in Venice by discovering the best things there are to see and do in the city.

Today’s itinerary in Venice covers several incredible sights, including a church and an art gallery. Start your adventure at Santa Maria Della Salute. This curiosity-inducing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the masterful wonders of Peggy Guggenheim Collection, a must-see art gallery 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 Gallerie Dell'accademia. This intriguing art gallery offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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 Venice. 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.

Don’t miss out on dining at Generator Venice, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Nevodi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

If you’re not ready to end the night just yet, Il Mercante offers a perfect venue to relax and savor a drink. Similarly, The Irish Pub Venezia is well-suited for those looking to unwind in a social setting. Ai Stagneri is another excellent spot to enjoy a nightcap after a delightful meal.

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

Embark on another extraordinary experience on day 5 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 3 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Ponte Vecchio. This globally renowned historical landmark provides an insightful glimpse into the city's identity. Next, discover Uffizi Gallery, a picture-perfect art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Palazzo Vecchio, a locally renowned palace. When you’re done, don’t forget to make a stop at the famous Piazza Della Signoria.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

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.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

Day 6 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, photo-friendly spots, and budget-friendly activities. Start at Central Market, a popular food market in the city. Then, head to Galleria Dell'accademia and soak in the ambiance of this history-steeped art gallery.

There are many interesting places to see in Florence, and when you are ready for more, go to Cathedral Of Santa Maria Del Fiore. This is one of the city’s most spectacular inviting spots of interest. After exploring the church, visit the increasingly popular Brunelleschi's Dome. Not far away, you'll also find Basilica Of Santa Croce In Florence. This church is a standout highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazzale Michelangelo, an impressive observation deck in the city.

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

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.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Porta Nuova is the first of them. Spend some time admiring this breathtaking historical landmark before continuing your journey. Parco Della Rocca is your next stop. This worthwhile park is one of the best-rated sights in Florence.

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 heritage-rich museum is a sight to behold. To round off your sightseeing experience, visit Villa Calcinaia - Conti Capponi.

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

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.

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

To truly maximize your evening out, consider visiting Gosh* after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Antico Caffè Del Moro - Art Bar Firenze, another bar with an inviting ambiance. Similarly, Quelo Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Savor another day of unforgettable experiences in Italy!

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 3 nights.

Savor the day by visiting some of the best places to see in Florence, including an archeological site, a monument, and a public square. Start your adventure at Roman Forum. This iconic archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Colosseum located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Arch Of Constantine. Its historic features will captivate you. After the monument, continue your tour of the city with a visit to Piazza Del Popolo. Visitors usually appreciate the visually striking features of this public square. Next up is Altare Della Patria, a highly recommended monument.

At the end of the day, you will drive to Rome, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you explore more of Rome, 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 dining experience at La Bottega Roma, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Pasta In Corso, 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 Trattoria Vecchia Roma. It’s yet another ideal choice to enhance your time in Rome tonight.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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 9 of your road trip, you’ll start and end your day in Rome, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Vatican City and Rome. You still have 2 nights left in Rome.

At the top of the list of things to do today is to explore Trastevere, a neighborhood that captures the true essence of Vatican City. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Start your adventure at Vatican Museums. This timeless art museum is a place that is appreciated by travelers and locals alike.

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. Peter's Basilica. This timeless major basilica offers an enriching experience. For a change of pace, head to Campo De' Fiori, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Piazza Navona. These sights offer a fulfilling end to a perfect day.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

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

Day 10 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s route brings fun adventures, romantic experiences, and natural wonders. The first attraction of today is Villa Borghese. This top-rated park is an idyllic place to see in Rome. Continue your discovery at Spanish Steps, an enchanting public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Di Spagna. This iconic public square offers a grand encounter with Rome. Next, make your way to Trevi Fountain to add another highlight to your day. After that, visit Pantheon, a globally renowned monument that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Castel Sant'angelo, an impressive castle 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 Rome.

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 Rome, 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 delicious meal at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 3 nights here for some well-deserved relaxation.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Pinacoteca Nazionale. This photogenic art gallery is sure to ignite your curiosity. Next, dive into the romantic features of Siena Cathedral, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Pubblico Palace, a locally appreciated palace. For a change of scene, check out Piazza Del Campo, known for its UNESCO world heritage-listed features. We also recommend visiting Tower Of Mangia. This monument is a must for anyone looking to experience the city to the fullest.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena 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 Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

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

On day 12 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 2 nights more, there’s no need to rush. Experience Siena and Castellina in Chianti to the fullest today with this curated day itinerary!

Siena is brimming with adventures. Today’s wonderful stops include a church, a palace, and a castle. Begin your sightseeing adventure at the locally appreciated Basilica Of San Domenico and allow yourself time to explore. Just a short distance away you'll find your next stop, Santuario Di Santa Caterina, a photogenic church that draws visitors from far and near.

Continue your journey to Palazzo Salimbeni, one of the city’s most frequently visited spots that you shouldn’t miss. Another great site to visit is the worthwhile Rocca Di Castellina In Chianti.

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start. You could also check out Bar Pinacoteca, offering a different kind of charm. A last recommendation for the day is San Paolo Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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.

Wake up to day 13 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a public square, a castle, and a monastery. Begin your adventure at Piazza Del Popolo. This is an often recommended public square you should not miss. Another must-see is Fortress Of Montalcino, a locally appreciated castle in Siena.

When you’re ready for the next sight, head to Abbey Of Sant'antimo.

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

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

Make sure to reserve a table at Ristorante San Desiderio, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Le Logge, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Taverna Di Cecco, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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 14 of your remarkable road trip in Italy. Today you will explore Padua, 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 Trieste. You’ll stay here for 1 night.

Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Prato Della Valle. This locally renowned public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is The Basilica Of St. Anthony, one of the city’s best highlights.

Next, check out Ragione Palace, one of the most frequently visited places to see in Siena. This palace is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Scrovegni Chapel. Wander around and soak in the respected atmosphere this church offers.

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.

Dine in style at Caffè degli Specchi, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Istriano Of Giobi And Oxa boasts a menu that's sure to impress. Also, be sure to check out Chimera di Bacco. Known as a local hotspot, it’s a great choice for tonight in Trieste.

Cap off your dinner by heading to "life" New Bar Torinese Snc, ideal for a leisurely evening with a drink in hand. White Cafe is another bar that offers an enjoyable setting. Similarly, Café James Joyce is also a popular place to go on a night out, perfect for relaxing and socializing.

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