14-Day Italy Self-Drive Road Trip With Itinerary from Trieste traveling west to Venice, Florence, Rome, Siena, and Bologna

Dive into day 2 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 2 nights.

Enjoy the perfect balance of relaxation and exploration in Trieste today. One of the most notable attractions included on the itinerary is Bridge Of Sighs. This history-steeped monument will help you start your sightseeing on top. Then, take a leisurely stroll to Doge's Palace and learn what makes this enchanting palace unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the captivating St Mark's Basilica. After exploring the church, head to Piazza San Marco. This wondrous public square is a highlight in Trieste. As your day continues, stop by Teatro La Fenice, known for its romantic features. Lastly, don’t forget to check out the world-famous Rialto Bridge. Enjoy exploring this incredible historical landmark at your own pace.

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.

Enjoy a delicious meal at Bauer Hotel, a top-rated dining destination in Venice. If you're in the mood to try something new, consider L'Osteria Le Guglie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

Continue the enjoyment post-dinner at Al Parlamento, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, The Caffe Rosso offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Adagio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day in Italy!

Day 3 of your road trip across Italy promises a magnificent time exploring Venice. You have 1 night left in Venice. Take the opportunity to experience more of the best attractions and activities in the city.

A top thing to do today is to explore Cannaregio, a must-see neighborhood in Venice. It's the perfect starting point for touring the top attractions in the area.

Today's adventure in Venice promises more breathtaking discoveries and enriching experiences! Begin at Grassi Palace. This romantic palace is a highlight of any visit in the city. Then, enjoy Peggy Guggenheim Collection, another awe-inspiring attraction that never fails to captivate visitors. Next, head over to Gallerie Dell'accademia, one of the city’s most up-and-coming attractions, known for its respected features.

If you’re looking for more, spend time soaking in the atmosphere of Santa Maria Gloriosa Dei Frari. This stunning church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Grand Canal, a locally appreciated street, and take a stroll around the area.

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.

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.

Explore the vibrant nightlife at Il Mercante after your meal, a hub for lively evenings and memorable moments. Or, head to The Irish Pub Venezia for a great selection of flavorful drinks and a charming setting. Furthermore, Ai Stagneri is perfect for those looking to extend their night with a touch of local flavor.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 3 nights.

A blend of family-friendly attractions, photo-friendly spots, and historic treasures await you in Venice on today’s itinerary. First up is the curiosity-inducing museum, Bargello National Museum. Afterward, continue to Uffizi Gallery, an art gallery every traveler should visit.

As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Ponte Vecchio. This globally renowned historical landmark is an essential stop. Following that, head to Loggia Dei Lanzi, another must-visit site that will enhance your experience. Don’t forget to stop by Palazzo Vecchio, a notable palace in the city. Finally, end your day with a visit to Piazza Della Signoria, an enchanting public square that offers the perfect conclusion to your sightseeing of the day.

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

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 5 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Oltrarno is a fantastic place you can explore today in Florence. 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 Florence-way-of-life and visit all the nearby sights.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a palace, a church, an art gallery, an observation deck and much more! Begin your adventure at Pitti Palace. This is a captivating palace you should not miss. Another must-see is Cathedral Of Santa Maria Del Fiore, an impressive church in Florence.

When you’re ready for the next sight, head to Galleria Dell'accademia. From there, take a leisurely stroll to Basilica Of Santa Croce In Florence, another of the city’s popular attractions. We recommend continuing your self-guided tour at Piazzale Michelangelo, a culturally significant place of 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.

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

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery 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.

Wake up to day 6 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!

Get ready to discover some of the most iconic wonders in Florence, including a castle, a monument, a public square, a museum, a park and much more! Start your day at Castle Of Verrazzano. This visually striking castle is a curiosity-inducing place to see in Florence. Then, wander over to Porta San Giovanni. If historic sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Del Duomo. This enchanting public square is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Palazzo Comunale, Pinacoteca, Torre Grossa is a locally appreciated spot in the town that will captivate you with its unique charm. When you’re done at the museum, don’t forget to check out the romantic Rocca Di Montestaffoli. Take a moment to appreciate the fascinating details of this curiosity-inducing castle. Wrap up your self-guided tour of Florence's top attractions with a visit to Parco Della Rocca.

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 3 nights here for some well-deserved relaxation.

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Colosseum. This iconic archeological site is an UNESCO world heritage-designated place to see in Florence. Continue your discovery at Roman Forum, a breathtaking archeological site with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Capitoline Hill. This interesting public square offers a masterful encounter with Florence. Next, make your way to Capitoline Museums to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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.

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

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

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

On day 8 of your road trip, you’ll start and end your day in Rome, where you'll stay for 2 nights more.

Make sure to visit Trastevere, a popular neighborhood in Vatican City. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Vatican Museums.

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

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

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 9 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Discover a day packed with fun adventures, photo-friendly spots, and history-rich sites in Rome. Begin your sightseeing with Basilica Di Santa Maria Maggiore. This interesting church is one of the top attractions in the city. Proceed to Spanish Steps, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Trevi Fountain. This timeless monument is a traveler-favorite. Not far away, you’ll find Pantheon, another key site on your sightseeing itinerary. Piazza Navona is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Castel Sant'angelo and uncover why it's recognized as one of the city's most astonishing attractions.

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.

Make sure to reserve a table at Hotel de Russie, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Taverna Italiana, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of The Parrot Bar, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at The Apartment Bar Roma. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Hotel Hassler Roma, the perfect place for those looking to experience the best of the nightlife.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Palazzo Salimbeni. This history-steeped palace is sure to ignite your curiosity. Next, dive into the culturally significant features of Battistero Di San Giovanni Battista, 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 Siena Cathedral, a locally renowned church. For a change of scene, check out Pubblico Palace, known for its culturally significant features. We also recommend visiting Piazza Del Campo. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Tower Of Mangia, yet another intriguing attraction in Rome.

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

On day 11 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 Asciano and Montalcino. You still have 1 night left in Siena.

Start your day with a visit to Crete Senesi Vista. This up-and-coming point of interest is a must-visit in the city. When you’re ready for your next discovery, continue to Fortress Of Montalcino, which may be one of the most romantic places you will experience today.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza Del Popolo, an up-and-coming public square in the city.

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

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.

Make sure to reserve a table at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 12 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 Bologna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the popular Two Towers, a picture-perfect monument in Siena. Next, go to Basilica Of San Domenico.

After visiting Two Towers and Basilica Of San Domenico, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Palazzo D'accursio. This historic palace offers a unique experience. Piazza Maggiore is another noteworthy attraction worthwhile a visit.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna 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 Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

Continue your evening by exploring the vibrant nightlife scene at Bar Al Bricco D'oro, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Freud E Squisito, a bar that offers unique local touches. Likewise, Osteria Del Sole provides an excellent alternative for a fun evening.

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

Dive into day 13 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.

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a public square, a church, a palace, a museum and much more! Begin your adventure at Prato Della Valle. This is a popular public square you should not miss. Another must-see is The Basilica Of St. Anthony, a notable church in Bologna.

When you’re ready for the next sight, head to Palazzo Zabarella. From there, take a leisurely stroll to Musei Civici Eremitani, another of the city’s intriguing attractions. We recommend continuing your self-guided tour at Scrovegni Chapel, a historic place of interest in the city.

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

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.

Dine in style at Rustiko, a top recommendation for dinner tonight. Or, for a change of pace, Caffè San Marco boasts a menu that's sure to impress. Also, be sure to check out Osteria Marise. Known as a local hotspot, it’s a great choice for tonight in Trieste.

Following your dinner, dive into the local bar culture at Mast. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Urbanis, the perfect place for those looking to experience the best of the nightlife. Similarly, Coktail Bar Trieste | La Preferita provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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