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

Day 2 of your road trip will take you to the best attractions Borgo Grotta Gigante / Briščiki has to offer. Cherish the 1 night you have left in Trieste by discovering the best things there are to see and do in the village.

Start by visiting Grotta Gigante, a prime spot to begin your journey. This gorgeous cave is sure to impress. Next on your list is Canale Ponterosso Trieste, another must-visit landmark and up-and-coming street renowned for its enchanting 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 romantic pier is an essential place to visit for anyone looking for the full Trieste experience. We also recommend visiting Piazza Unità D'italia, an interesting 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 romantic 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.

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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Mast, known for its inviting atmosphere. Urbanis is another great option if you’re looking for a place to get the night started. Similarly, Coktail Bar Trieste | La Preferita provides a great setting to enjoy the night away.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Venice. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 2 nights.

Trieste is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Bridge Of Sighs, a notable monument that is worthwhile a visit in the city. Nearby, you’ll find Doge's Palace, enchanting visitors with its grand appeal. Continue your exploration at St Mark's Basilica. This church is one of the city’s most notable spots.

Enjoy the freedom of exploring Trieste at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit St Mark's Campanile. After exploring the monument, head to the timeless Piazza San Marco. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Rialto Bridge, a place of visually striking interest in Trieste.

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.

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

Treat yourself to a delicious dinner at Bauer Hotel, an excellent option for tonight's dining. Looking for something different? L'Osteria Le Guglie offers a tantalizing alternative with its diverse menu. And don’t miss Corner Pub. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

Continue your evening by exploring the vibrant nightlife scene at Al Parlamento, a prime destination for a thrilling night out. Also, don’t forget to check out The Caffe Rosso, a bar that offers unique local touches. Likewise, Adagio provides an excellent alternative for a fun evening.

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

Day 4 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Venice. Begin your sightseeing with Santa Maria Della Salute. This curiosity-inducing church is one of the top attractions in the city. Proceed to Peggy Guggenheim Collection, another must-visit attraction.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Gallerie Dell'accademia. This beloved art gallery is a traveler-favorite.

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.

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 Generator Venice, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Nevodi? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante La Piazza as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Venice.

Round off your dining experience by visiting Il Mercante, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Irish Pub Venezia, a bar catering to every mood and preference. Ai Stagneri likewise offers a unique atmosphere, perfect for a memorable night out.

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.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the timeless Ponte Vecchio, a visually striking historical landmark in Venice. Next, go to Uffizi Gallery.

After visiting Ponte Vecchio and Uffizi Gallery, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to Palazzo Vecchio. This visually striking palace offers a unique experience. Piazza Della Signoria is another noteworthy attraction worthwhile a visit.

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.

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 Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Celebrate another amazing day of your road trip adventure 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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Central Market. This visually striking food market is a highlight of any visit in the city. Then, enjoy Galleria Dell'accademia, another detailed attraction that never fails to captivate visitors. Next, head over to Cathedral Of Santa Maria Del Fiore, one of the city’s most top-rated attractions, known for its UNESCO world heritage-designated features.

If you’re looking for more, spend time soaking in the atmosphere of Brunelleschi's Dome. This visually striking monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Basilica Of Santa Croce In Florence, a locally renowned church, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazzale Michelangelo before you head back to your hotel.

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 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.

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.

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.

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

Wake up to day 7 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Porta Nuova. This curiosity-inducing historical landmark is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Parco Della Rocca, one of the hamlet’s best highlights.

Next, check out Sangimignano1300, one of the most curiosity-inducing places to see in Florence. This museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Villa Calcinaia - Conti Capponi. Wander around and soak in the awe-inspiring atmosphere this winery offers.

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.

Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. 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!

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.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Roman Forum is the perfect place to start. This archeological site is one of the most wondrous places to visit in Florence. Next, head to Colosseum, a globally renowned archeological site, known for its picture-perfect 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 Arch Of Constantine. This picture-perfect monument is a highly recommended experience. Nearby, you'll also find Piazza Del Popolo and Altare Della Patria. Visit these for an interesting touch to your journey.

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.

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

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.

At the end of the day, you'll drive back to Rome, where you'll stay for 2 nights more.

Trastevere is a fantastic place you can explore today in Vatican City. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Vatican City-way-of-life and visit all the nearby sights.

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 globally renowned major basilica offers an enriching experience. For a change of pace, head to Campo De' Fiori, where you can take in history-steeped 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 the area’s best attractions, you’ll drive back to your accommodation in Rome.

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

Enjoy a lovely dining experience at RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

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

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

On day 10 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Today’s agenda in Rome includes a park, a public square, a monument, a castle and much more! Villa Borghese is must-visit park and a great starting point for the day. Next, continue your journey to Spanish Steps, an astonishing public square, located just a leisurely stroll away. Next, head to Piazza Di Spagna, an awe-inspiring public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the wondrous Trevi Fountain. If you’re looking for more, Pantheon is also a wondrous attraction that is worthwhile a visit. Lastly, don’t miss Castel Sant'angelo, a place of history-steeped interest 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.

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.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Keep the evening going at The Apartment Bar Roma, a great choice for enjoying the after-dinner hours with a drink. You could also go to Hotel Hassler Roma, which offers a similarly pleasant setting and great drinks.

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

On day 11 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. In the evening, you’ll end up in Siena, where you will stay for 3 nights.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, picturesque spots, and history-rich sites. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Pinacoteca Nazionale is the first of them. Spend some time admiring this historic art gallery before continuing your journey. Siena Cathedral is your next stop. This captivating church is one of the best-rated sights in Rome.

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 Pubblico Palace. This culturally significant palace is a sight to behold. To round off your sightseeing experience, visit Piazza Del Campo and Tower Of Mangia.

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.

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 delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

On day 12 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Siena and Castellina in Chianti. You still have 2 nights left in Siena.

Discover a day packed with fun adventures, scenic views, and picturesque spots in Siena. Begin your sightseeing with Basilica Of San Domenico. This beloved church is one of the top attractions in the city. Proceed to Santuario Di Santa Caterina, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Palazzo Salimbeni. This up-and-coming palace is a traveler-favorite. Not far away, you’ll find Rocca Di Castellina In Chianti, another key site on your sightseeing itinerary.

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.

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Fischi per Fiaschi? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Pinacoteca, a bar that offers unique local touches. Likewise, San Paolo Pub provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences in Italy!

On day 13 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 1 night more, there’s no need to rush. Experience Montalcino and Castelnuovo dell'Abate to the fullest today with this curated day itinerary!

Siena is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Piazza Del Popolo, an up-and-coming public square that is worthwhile a visit in the village. Nearby, you’ll find Fortress Of Montalcino, enchanting visitors with its history-steeped appeal. Continue your exploration at Abbey Of Sant'antimo. This monastery is one of the village’s most up-and-coming spots.

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

As you explore more of Siena, 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.

Dine in style at Ristorante San Desiderio, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Le Logge boasts a menu that's sure to impress. Also, be sure to check out Ristorante Taverna Di Cecco. Known as a local hotspot, it’s a great choice for tonight in Siena.

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

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Padua. 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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, romantic experiences, and scenic views. Start at Prato Della Valle, an interesting public square in the city. Then, head to The Basilica Of St. Anthony and soak in the ambiance of this heritage-rich church.

There are many interesting places to see in Siena, and when you are ready for more, go to Ragione Palace. This is one of the city’s most curiosity-inducing breathtaking spots of interest. After exploring the palace, visit the well-known Scrovegni Chapel.

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 meal at Caffè degli Specchi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Istriano Of Giobi And Oxa is another top choice with a popular menu. You could also check for a table at Chimera di Bacco. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Trieste tonight.

Keep the evening going at "life" New Bar Torinese Snc, a great choice for enjoying the after-dinner hours with a drink. You could also go to White Cafe, which offers a similarly pleasant setting and great drinks. Another option is Café James Joyce, which provides an inviting environment for unwinding after a busy day out.

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