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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Venice. At the end of the day, you will retreat to the hotel of your choice in Venice, where will spend 2 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Venice may take around 2 hours 17 min. Upon your arrival in Venice, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Set out on a self-guided sightseeing tour at Bridge Of Sighs and explore the romantic features. Next, make your way to Doge's Palace, another highlight in Venice. When you’re done exploring the palace, continue to St Mark's Basilica, an UNESCO world heritage-listed church.

Nearby, you will also find Piazza San Marco. This world-famous public square is a top place to see in the area. Lastly, head to Teatro La Fenice, a picture-perfect opera house that is perfect for some final exploring in the city.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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.

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

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

Day 3 of your road trip will take you to the best attractions Venice has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Venice.

Set aside time today to explore Cannaregio, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Grassi Palace is must-visit palace and a great option for a daytime tour of the area. Continue your journey to Peggy Guggenheim Collection, a well-known art gallery, located just a leisurely stroll away. Next, head to Gallerie Dell'accademia, a history-steeped art gallery, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Venice. When you're ready, let your sightseeing route take you to the intriguing Santa Maria Gloriosa Dei Frari. If you’re looking for more, Grand Canal is also an often recommended attraction that is worthwhile a visit.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Venice is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Venice.

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.

Unwind after your meal by stepping into Il Mercante. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, The Irish Pub Venezia offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Ai Stagneri, another top-rated bar in the area.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Florence. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 3 nights.

When you’ve had your share of Venice, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Florence. Your travel time is around 2 hours 56 min.

One of our top recommendations for your sightseeing is Bargello National Museum. Spend some time admiring the photogenic features of the museum before you continue to your next stop. Then, head to Uffizi Gallery. This impressive art gallery is a traveler-favorite in the city.

If you're keen to see more, continue to Ponte Vecchio. Feed your curiosity by learning something new about the historical landmark. Next, take your journey to Loggia Dei Lanzi, a frequently visited public square. Conclude your sightseeing at Palazzo Vecchio, known for its romantic features.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax 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.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

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

On day 5 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 2 nights.

Florence is brimming with adventures. Oltrarno is a neighborhood that stands out as one of the must-see places in Florence. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Your adventure in Florence is only getting started when you visit Pitti Palace, a captivating local hot spot. Another notable attraction to explore is Cathedral Of Santa Maria Del Fiore. This top-rated church is known for its instagrammable appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Galleria Dell'accademia. This photogenic art gallery offers a fascinating experience that many visitors find memorable. Basilica Of Santa Croce In Florence is also worth visiting, along with Piazzale Michelangelo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Greve in Chianti and San Gimignano. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Greve in Chianti is brimming with adventures.

Set your GPS to Greve in Chianti and hit the road. Expect a journey of approximately 46 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greve in Chianti beckons with new experiences!

For a more meaningful self-guided tour of the town's best attractions, visit Castle Of Verrazzano, a locally appreciated castle that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’re ready to jump back into the car and say goodbye to Greve in Chianti, you’ll hit the road in the direction of San Gimignano. This drive usually takes around 52 min.

For a more meaningful self-guided tour of the town's best attractions, visit Porta San Giovanni, a worthwhile monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Piazza Del Duomo and admire its visually striking features.

When you’re ready, continue to Palazzo Comunale, Pinacoteca, Torre Grossa, an underrated museum beloved by locals and tourists alike. Don't miss out on Rocca Di Montestaffoli, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Parco Della Rocca, a romantic place to see that you won’t regret spending some extra time discovering.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

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.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Rome, where you’ll be staying for 3 nights.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Rome. This drive usually takes around 3 hours 9 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Colosseum, a wondrous archeological site that everyone visiting Rome should see. Next, head to Roman Forum. This picture-perfect archeological site is one of the most globally renowned attractions in the region.

If you're keen to see more, don’t miss out on Capitoline Hill, a romantic public square popular among locals as well as travelers. Capitoline Museums is an excellent attraction to visit next. Spend some time learning more about this locally renowned museum before you continue 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.

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.

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.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

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

On day 8 of your road trip, you’ll start and end your day in Rome, where you have 2 nights left to stay.

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.

No visit to Rome is complete without Fontana Dell'acqua Paola. This beloved monument is one of the top attractions in the city.

It’s time to gear up for the next part of your road trip adventure. Set course for Vatican City! Under favorable conditions, your drive to Vatican City may take around 12 min. Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Next, continue your sightseeing at Saint Peter's Square, a well-known square.

Make sure to also explore St. Peter's Basilica, a timeless major basilica.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Head back to your accommodation in Rome and get some rest to prepare for another magical day of your road trip in Italy.

Day 9 offers an itinerary packed with the best things to see in Trieste. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

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.

One of the most well-known attractions included on the itinerary is Basilica Di Santa Maria Maggiore. This photogenic church will help you start your sightseeing on top. Then, take a leisurely stroll to Spanish Steps and learn what makes this history-steeped public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Trevi Fountain. After exploring the monument, head to Pantheon. This iconic monument is a highlight in Rome. As your day continues, stop by Piazza Navona, known for its visually striking features. Lastly, don’t forget to check out the top-rated Castel Sant'angelo. Enjoy exploring this incredible castle at your own pace.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

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.

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.

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

On day 10 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Throughout the day, make sure to take breaks to appreciate the surroundings.

After soaking in Rome’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 2 hours 42 min. When you arrive in Siena, it's time to take a break from the road.

Our first attraction recommendation in Siena is Palazzo Salimbeni, a beloved palace that draws attention for its instagrammable features. Spend some time soaking in the atmosphere before continuing to Battistero Di San Giovanni Battista, a photogenic church that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Siena Cathedral, a notable church that offers a unique experience. Be sure to also explore Pubblico Palace, a nearby palace, highly recommended by other travelers. End your self-guided tour at Piazza Del Campo, a history-steeped public square and the perfect final attraction in Siena.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Make sure to reserve a table at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei, a hidden gem nestled in Siena. 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 Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

Savor another day of unforgettable experiences in Italy!

On day 11 of your road trip, you’ll start and end your day in Siena, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Asciano and Montalcino.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Asciano. Your travel time is around 46 min.

One of our top recommendations for your sightseeing is Crete Senesi Vista.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Montalcino. This drive usually takes around 30 min, without any stops or traffic disruptions.

Spend your afternoon discovering Fortress Of Montalcino, an up-and-coming castle known for its respected features. Next, continue your sightseeing at Piazza Del Popolo, an underrated public square.

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 a true cultural experience.

Enjoy a lovely dining experience at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

Explore the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Pinacoteca for a great selection of flavorful drinks and a charming setting. Furthermore, San Paolo Pub is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass to another unforgettable day in Italy!

Your itinerary for day 12 of your road trip in Italy includes 1 stop and features some of the highlights of Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Bologna. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 15 min. Upon reaching Bologna, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Two Towers is a well-known monument we recommend visiting today. Discover its breathtaking features before continuing your self-guided tour to Basilica Of San Domenico, a photogenic church that’s well-regarded in the area.

Next, stop by Palazzo D'accursio, a historic palace. While you’re nearby, don’t forget to visit Piazza Maggiore, a grand and truly unique public square.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and relax before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Bologna, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. Known for great service, it’s a fantastic choice for tonight in Bologna.

Extend your evening after a delightful meal by visiting Bar Al Bricco D'oro, which offers the perfect atmosphere for a night out. Moreover, Bar Freud E Squisito is another popular option for a drink or two. Likewise, Osteria Del Sole 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!

Experience an unparalleled adventure on day 13 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Padua. At the end of the day, you will retreat to the hotel of your choice in Trieste, where will spend 1 night.

Padua’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Bologna behind. This drive usually takes around 1 hour 30 min. Padua welcomes you with a multitude of unique vacation experiences.

Spend your afternoon discovering Prato Della Valle, an interesting public square known for its visually striking features. Next, continue your sightseeing at The Basilica Of St. Anthony, a notable church.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Palazzo Zabarella and uncover the details of this heritage-rich palace. Make sure to also explore Musei Civici Eremitani, a beloved museum. For your last stop, consider Scrovegni Chapel, an UNESCO world heritage-designated church that many travelers find worth the detour.

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.

Indulge in a memorable dining experience at one of Trieste's most popular restaurants, and connect with friendly locals for a true cultural experience.

Treat yourself to a wonderful meal at Rustiko, a top-rated dining spot in Trieste. If you're in the mood for something new, try Caffè San Marco, another premier location with a delectable menu. You might also want to book a table at Osteria Marise. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Trieste.

After savoring a delicious meal, step into the vibrant nightlife at Mast, where the evening is just getting started. In the same way, Urbanis offers a unique charm perfect for experiencing the local bar scene in Trieste. Coktail Bar Trieste | La Preferita is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.