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 vibrant destinations - Venice. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Venice. You will spend 2 nights here for some well-deserved relaxation.

Trieste is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic 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 UNESCO world heritage-listed appeal. Continue your exploration at St Mark's Basilica. This church is one of the city’s most well-known 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 Piazza San Marco. After exploring the public square, head to the locally renowned Teatro La Fenice. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Rialto Bridge, a place of romantic interest in Trieste.

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.

Treat yourself to a wonderful meal at Bauer Hotel, a top-rated dining spot in Venice. If you're in the mood for something new, try L'Osteria Le Guglie, another premier location with a delectable menu. You might also want to book a table at Corner Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Venice.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Caffe Rosso, a bar catering to every mood and preference. Adagio 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!

Day 3 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

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.

Venice is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Grassi Palace, an intriguing palace that is worthwhile a visit in the city. Nearby, you’ll find Peggy Guggenheim Collection, enchanting visitors with its enchanting appeal. Continue your exploration at Gallerie Dell'accademia. This art gallery is one of the city’s most increasingly popular spots.

Enjoy the freedom of exploring Venice at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Santa Maria Gloriosa Dei Frari. After exploring the church, head to the beloved Grand Canal.

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 Venice. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at Generator Venice, a top recommendation for dinner tonight. Or, for a change of pace, Nevodi boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Piazza. Known as a local hotspot, it’s a great choice for tonight in Venice.

After your meal, keep the night alive at a bar like Il Mercante, known for its lively atmosphere. The Irish Pub Venezia is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Ai Stagneri offers an excellent atmosphere for those looking to amp up the evening.

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

On day 4 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 Florence. In the evening, you’ll end up in Florence, where you will stay 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 Bargello National Museum. This curiosity-inducing museum provides an insightful glimpse into the city's identity. Next, discover Uffizi Gallery, a picture-perfect art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Ponte Vecchio, an iconic historical landmark. When you’re done, don’t forget to make a stop at the often recommended Loggia Dei Lanzi. Not far away from the public square, you will find the romantic Piazza Della Signoria, perfect for a quick visit. Round off your day at Palazzo Vecchio, another gem in Venice with romantic features to discover.

At the end of the day, you will drive to Florence, 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 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.

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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 5 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

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

Get ready to discover some of the most iconic wonders in Florence, including a palace, a church, an art gallery, an observation deck and much more! Start your day at Pitti Palace. This visually striking palace is a locally renowned place to see in Florence. Then, wander over to Cathedral Of Santa Maria Del Fiore. If visually striking sites excite you, this church will be right up your alley. Nearby, you’ll also find Galleria Dell'accademia. This detailed art gallery 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, Basilica Of Santa Croce In Florence is a captivating spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the symbolic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this top-rated observation deck.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

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

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery 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!

On day 6 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Greve in Chianti and San Gimignano. You still have 1 night left in Florence.

Savor the day by visiting some of the best places to see in Florence, including a castle, a monument, a public square, a museum, a park and much more! Start your adventure at Castle Of Verrazzano. This curiosity-inducing castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta San Giovanni located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Del Duomo. Its romantic features will captivate you. After the public square, continue your tour of the town with a visit to Palazzo Comunale, Pinacoteca, Torre Grossa. Visitors usually appreciate the historic features of this museum. Next up is Rocca Di Montestaffoli, a highly recommended castle. For a change of pace, head to Parco Della Rocca. As one of the most often recommended attractions in Florence, this park is the perfect place to end your self-guided sightseeing tour.

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

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.

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar 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.

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

Today, you'll explore some of the most beautiful places in Florence, including an archeological site, a public square, and a museum. Start your day with a visit to Colosseum. This globally renowned archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Roman Forum, which may be one of the most historic places you will experience today.

One of the best things about exploring Florence 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 Capitoline Hill, a well-known public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Capitoline Museums.

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

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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!

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

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.

Continue your journey to Sistine Chapel, one of the city’s most widely recognized spots that you shouldn’t miss. Another great site to visit is the wondrous St. Peter's Basilica. When you're finished at the major basilica, Fontana Dell'acqua Paola awaits your visit. This monument is a romantic highlight on today's itinerary.

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

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

Enjoy a delicious meal 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.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Say good night to Rome and look forward to another great day of your road trip 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.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most locally renowned attractions included on the itinerary is Basilica Di Santa Maria Maggiore. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Spanish Steps and learn what makes this culturally significant 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 world-famous monument is a highlight in Rome. As your day continues, stop by Piazza Navona, known for its history-steeped features. Lastly, don’t forget to check out the spectacular Castel Sant'angelo. Enjoy exploring this incredible castle at your own pace.

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 Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Explore the vibrant nightlife at The Apartment Bar Roma after your meal, a hub for lively evenings and memorable moments. Or, head to Hotel Hassler Roma for a great selection of flavorful drinks and a charming setting.

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

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Palazzo Salimbeni is the perfect place to start. This palace is one of the most curiosity-inducing places to visit in Rome. Next, head to Battistero Di San Giovanni Battista, an increasingly popular church, known for its culturally significant 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 Siena Cathedral. This history-steeped church is a highly recommended experience. Nearby, you'll also find Pubblico Palace and Piazza Del Campo. Visit these for an interesting touch to your journey. Finish the day with a visit to Tower Of Mangia, a historic monument 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 delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

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

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

Wake up to day 11 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Begin your adventure at Crete Senesi Vista. This is a worthwhile point of interest you should not miss. Another must-see is Fortress Of Montalcino, a frequently visited castle in Siena.

When you’re ready for the next sight, head to Piazza Del Popolo.

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

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

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Pinacoteca is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, San Paolo Pub ensures a night out tailored to your taste.

Savor another day of unforgettable experiences in Italy!

Dive into day 12 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Bologna. You’ll stay here for 1 night.

Prepare for a day full of fun adventures, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Two Towers. This well-known monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of San Domenico, one of the city’s best highlights.

Next, check out Palazzo D'accursio, one of the most underrated places to see in Siena. This palace is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Maggiore. Wander around and soak in the history-steeped atmosphere this public square offers.

At the end of the day, you will drive to Bologna, 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 Bologna. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

If you’re not ready to end the night just yet, Bar Al Bricco D'oro offers a perfect venue to relax and savor a drink. Similarly, Bar Freud E Squisito is well-suited for those looking to unwind in a social setting. Osteria Del Sole is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day 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 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.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Prato Della Valle. This well-known public square is a romantic place to see in Bologna. Continue your discovery at The Basilica Of St. Anthony, a monumental church with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Palazzo Zabarella. This curiosity-inducing palace offers a heritage-rich encounter with Bologna. Next, make your way to Musei Civici Eremitani to add another highlight to your day. After that, visit Scrovegni Chapel, a well-known church that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

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.

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.

Have a fantastic dining experience at Rustiko, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffè San Marco offers an enticing alternative with its varied menu. Additionally, Osteria Marise is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Trieste.

Explore the vibrant nightlife at Mast after your meal, a hub for lively evenings and memorable moments. Or, head to Urbanis for a great selection of flavorful drinks and a charming setting. Furthermore, Coktail Bar Trieste | La Preferita is perfect for those looking to extend their night with a touch of local flavor.

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.