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.

Start by visiting Grotta Gigante, a prime spot to begin your journey. This picturesque cave is sure to impress. Next on your list is Canale Ponterosso Trieste, another must-visit landmark and curiosity-inducing street renowned for its visually striking 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 Molo Audace. This history-steeped pier is an essential place to visit for anyone looking for the full Trieste experience. We also recommend visiting Piazza Unità D'italia, a captivating public square. Nearby, you'll also find Revoltella Museum, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Miramare Castle and wrap up your day with its history-steeped appeal.

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.

Experience shopping bliss at Trieste as you explore Piazza Unità d'Italia. Take a leisurely stroll through unique boutiques and shops, where local treasures are waiting to be found. Beyond shopping, Piazza Unità d'Italia offers more options, including cafes, unique attractions, key services, and vibrant events.

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.

Savor the flavors at Rustiko, a top pick for dinner tonight. Alternatively, Caffè San Marco beckons with its unique menu offerings. Also, consider Osteria Marise. With its consistent customer satisfaction, it’s an excellent option for dining in Trieste tonight.

If you’re not ready to end the night just yet, Mast offers a perfect venue to relax and savor a drink. Similarly, Urbanis is well-suited for those looking to unwind in a social setting. Coktail Bar Trieste | La Preferita is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences 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 agenda in Trieste includes a monument, a palace, a church, a public square, a historical landmark and much more! Bridge Of Sighs is must-visit monument and a great starting point for the day. Next, continue your journey to Doge's Palace, a locally renowned palace, located just a leisurely stroll away. Next, head to St Mark's Basilica, a history-steeped church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Trieste. When you're ready, let your sightseeing route take you to the often recommended St Mark's Campanile. If you’re looking for more, Piazza San Marco is also a wondrous attraction that is worthwhile a visit. Lastly, don’t miss Rialto Bridge, a place of romantic interest in the city.

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.

Have a fantastic dining experience at Bauer Hotel, a highly recommended choice for tonight's dinner. If you're looking to mix things up, L'Osteria Le Guglie offers an enticing alternative with its varied menu. Additionally, Corner Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

After enjoying a fulfilling meal, continue your evening at Al Parlamento, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Caffe Rosso offers a welcoming atmosphere for easing into the nightlife. Similarly, Adagio provides an excellent environment for a relaxed and enjoyable evening.

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.

Get ready for an exciting day in Venice. Today’s sightseeing agenda includes a church and an art gallery. Begin your adventure at Santa Maria Della Salute. This is a locally appreciated church you should not miss. Another must-see is Peggy Guggenheim Collection, a captivating art gallery in Venice.

When you’re ready for the next sight, head to Gallerie Dell'accademia.

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 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 Generator Venice, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Nevodi is another top choice with a popular menu. You could also check for a table at Ristorante La Piazza. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Venice tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Il Mercante, known for its inviting atmosphere. The Irish Pub Venezia is another great option if you’re looking for a place to get the night started. Similarly, Ai Stagneri provides a great setting to enjoy the night away.

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

Dive into day 5 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 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 wondrous historical landmark provides an insightful glimpse into the city's identity. Next, discover Uffizi Gallery, a romantic art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Palazzo Vecchio, a well-known palace. When you’re done, don’t forget to make a stop at the widely recognized 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.

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

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

Savor another day of unforgettable experiences in Italy!

Day 6 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Florence is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and wallet-friendly activities! Start at Central Market, a notable food market that is worthwhile a visit in the city. Nearby, you’ll find Galleria Dell'accademia, enchanting visitors with its photogenic appeal. Continue your exploration at Cathedral Of Santa Maria Del Fiore. This church is one of the city’s most astonishing spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Brunelleschi's Dome. After exploring the monument, head to the well-known Basilica Of Santa Croce In Florence. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazzale Michelangelo, a place of enchanting interest in Florence.

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 Florence. 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.

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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

As the sun sets on another day of adventure, rest up and recharge for the next leg 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 agenda in Florence includes a historical landmark, a park, a museum, a winery and much more! Porta Nuova is must-visit historical landmark and a great starting point for the day. Next, continue your journey to Parco Della Rocca, an often recommended park, located just a leisurely stroll away. Next, head to Sangimignano1300, an eye-catching museum, also available for your discovery today.

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

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Gosh*, a perfect place for winding down or revving up the night, depending on which mood you’re in. Antico Caffè Del Moro - Art Bar Firenze is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Quelo Bar ensures a night out tailored to your taste.

Take some time to reflect on your day and savor another beautiful night 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 Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Florence is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Roman Forum, a wondrous archeological site that is worthwhile a visit in the city. Nearby, you’ll find Colosseum, enchanting visitors with its UNESCO world heritage-listed appeal. Continue your exploration at Arch Of Constantine. This monument is one of the city’s most underrated spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Del Popolo. After exploring the public square, head to the locally renowned Altare Della Patria.

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 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 La Bottega Roma, a highly-rated dining destination in Rome. If you're eager to try something different, consider Pasta In Corso, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.

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

Wake up to day 9 of your extraordinary road trip in Italy. With 2 nights left in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Don’t miss Trastevere in Vatican City today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Rome is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and picturesque spots! Start at Vatican Museums, a wondrous art museum that is worthwhile a visit in the city. Continue your exploration at St. Peter's Basilica. This major basilica is one of the city’s most globally renowned spots.

Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Campo De' Fiori. After exploring the public square, head to the globally renowned Piazza Navona.

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

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.

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

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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

Day 10 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Rome covers several incredible sights, including a park, a public square, a monument, a castle and much more! Start your adventure at Villa Borghese. This impressive park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Spanish Steps, a must-see public square 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 Piazza Di Spagna. This iconic public square offers an enriching experience. For a change of pace, head to Trevi Fountain, where you can take in enchanting features. Conclude your self-guided sightseeing tour with a visit to Pantheon and Castel Sant'angelo. 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.

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

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

Celebrate another amazing day of your road trip adventure 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.

Get ready to discover some of the most iconic wonders in Rome, including an art gallery, a church, a palace, a public square, a monument and much more! Start your day at Pinacoteca Nazionale. This standout art gallery is a worthwhile place to see in Rome. Then, wander over to Siena Cathedral. If history-steeped sites excite you, this church will be right up your alley. Nearby, you’ll also find Pubblico Palace. This picture-perfect palace is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Del Campo is a famous spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the culturally significant Tower Of Mangia. Take a moment to appreciate the fascinating details of this intriguing monument.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

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

Greet day 12 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena for your remaining 2 nights 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 Siena and Castellina in Chianti.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Basilica Of San Domenico. This underrated church provides an insightful glimpse into the city's identity. Next, discover Santuario Di Santa Caterina, a heritage-rich church, promising a delightful encounter.

Continue your sightseeing with a visit to Palazzo Salimbeni, a worthwhile palace. When you’re done, don’t forget to make a stop at the worthwhile Rocca Di Castellina In Chianti.

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

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

Have a fantastic dining experience at Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Unwind after your meal by stepping into Charlie Mixology Bar Di Aldinucci Riccardo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Pinacoteca offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook San Paolo Pub, another top-rated bar in the area.

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

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

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 underrated public square you should not miss. Another must-see is Fortress Of Montalcino, an up-and-coming castle in Siena.

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

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

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

Enjoy a lovely dining experience at Ristorante San Desiderio, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Osteria Le Logge, 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 Ristorante Taverna Di Cecco. It’s yet another ideal choice to enhance your time in Siena tonight.

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

On day 14 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Padua. When you’re not sightseeing, take time to relax at your selected hotel in Trieste, where you’ll be staying for 1 night.

Siena is brimming with adventures. Today’s wonderful stops include a public square, a church, and a palace. Begin your sightseeing adventure at the popular Prato Della Valle and allow yourself time to explore. Just a short distance away you'll find your next stop, The Basilica Of St. Anthony, a culturally significant church that draws visitors from far and near.

Continue your journey to Ragione Palace, one of the city’s most beloved spots that you shouldn’t miss. Another great site to visit is the well-known Scrovegni Chapel.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Trieste. Trieste offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

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.

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.

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