9-Day Italy Self-Drive Road Trip With Itinerary from Trieste traveling west to Venice and Florence

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Explore the best of Italy on a 9-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Trieste, Venice, Bologna, Florence, Siena, Pisa, and Lucca. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Trieste, 2 nights in Venice, and 4 nights in Florence. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Trieste, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Piazza San Marco and Rialto Bridge are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Ponte Vecchio, learn more about the unique Leaning Tower Of Pisa, and immerse yourself in the vibrant atmosphere of Piazza Del Duomo, Pisa.

As you hit the open road and drive through Trieste, Venice, Bologna, Florence, Siena, Pisa, and Lucca, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Unity of Italy Square
Bridge of SighsDoge's PalaceSt Mark's BasilicaPiazza San MarcoTeatro La FeniceRialto Bridge
Grand CanalBasilica S.Maria Gloriosa dei FrariGallerie dell'AccademiaPeggy Guggenheim Collection
Piazza MaggioreBiblioteca comunale dell'ArchiginnasioBasilica of San Domenico
piazzale MichelangeloPonte VecchioUffizi GalleryPalazzo Vecchiopiazza della SignoriaCathedral of Santa Maria del Fiore
Fortezza MediceaBasilica of San DomenicoSiena Cathedralpiazza del CampoTower of MangiaPubblico Palace

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Day 1

Day 1

  • Triest - Arrival day
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  • Unity of Italy Square
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Your road trip adventure in Italy begins as soon as you reach Trieste and pick up your car. You’ll stay in Trieste for 1 night and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Trieste is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Piazza Unità D'italia, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Trieste. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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 Trieste, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Murphy's Meeting Point, an excellent option for tonight's dining. Looking for something different? Caffè Tommaseo offers a tantalizing alternative with its diverse menu. And don’t miss Al Barattolo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Trieste.

Cap off your dinner by heading to Bar G, ideal for a leisurely evening with a drink in hand. Bar X is another bar that offers an enjoyable setting. Similarly, Antico Caffè Torinese is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise a toast to the start of your 9-day road trip in Italy!

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Day 2

Day 2

  • Triest
  • Venice
  • More

Drive 167 km, 2 hours 40 min

  • Bridge of Sighs
  • Doge's Palace
  • St Mark's Basilica
  • Piazza San Marco
  • Teatro La Fenice
  • Rialto Bridge
  • More

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

Enjoy the perfect balance of relaxation and exploration in Trieste today. One of the most captivating attractions included on the itinerary is Bridge Of Sighs. This culturally significant 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 well-known St Mark's Basilica. After exploring the church, head to Piazza San Marco. This globally renowned public square is a highlight in Trieste. As your day continues, stop by Teatro La Fenice, known for its instagrammable features. Lastly, don’t forget to check out the world-famous Rialto Bridge. Enjoy exploring this incredible historical landmark at your own pace.

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

Enjoy a 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 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.

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.

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Day 3

Day 3

  • Venice
  • More

Drive 5 km, 42 min

  • Grand Canal
  • Basilica S.Maria Gloriosa dei Frari
  • Gallerie dell'Accademia
  • Peggy Guggenheim Collection
  • More

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 Venice by discovering the best things there are to see and do in the city.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Grand Canal. This beloved street provides an insightful glimpse into the city's identity. Next, discover Santa Maria Gloriosa Dei Frari, a grand church, promising a delightful encounter.

Continue your sightseeing with a visit to Gallerie Dell'accademia, a locally appreciated art gallery. When you’re done, don’t forget to make a stop at the notable Peggy Guggenheim Collection.

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 delicious dinner at Generator Venice, an excellent option for tonight's dining. Looking for something different? Nevodi offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante La Piazza. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Il Mercante, a well-loved spot among locals and tourists. Or, head to The Irish Pub Venezia. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ai Stagneri, another top-rated place in the area.

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

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Day 4

Day 4

  • Venice
  • Florence
  • More

Drive 272 km, 3 hours 33 min

  • Piazza Maggiore
  • Biblioteca comunale dell'Archiginnasio
  • Basilica of San Domenico
  • More

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

Get ready for an exciting day in Venice. Today’s sightseeing agenda includes a public square, a library, and a church. Begin your adventure at Piazza Maggiore. This is an impressive public square you should not miss. Another must-see is Biblioteca Comunale Dell'archiginnasio, an increasingly popular library in Venice.

When you’re ready for the next sight, head to Basilica Of San Domenico.

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 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 Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

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

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Day 5

Day 5

  • Florence
  • More

Drive 4 km, 1 hour 5 min

  • piazzale Michelangelo
  • Ponte Vecchio
  • Uffizi Gallery
  • Palazzo Vecchio
  • piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • More

Day 5 offers a multitude of experiences. You will stay in Florence for 3 nights more, offering you enough time to explore at a relaxed pace.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazzale Michelangelo. This famous observation deck is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Ponte Vecchio, one of the city’s best highlights.

Next, check out Uffizi Gallery, one of the most spectacular places to see in Florence. This art gallery is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Palazzo Vecchio. Wander around and soak in the romantic atmosphere this palace offers. Then, head to Piazza Della Signoria, a top-rated public square that adds another dimension to your day. Finally, visit the widely recognized Cathedral Of Santa Maria Del Fiore, the last of our attraction recommendations for today.

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

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

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

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.

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

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Day 6

Day 6

  • Florence
  • More

Drive 154 km, 2 hours 53 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Pubblico Palace
  • More

On day 6 of your road trip, you’ll start and end your day in Florence, where you'll stay for 2 nights more.

Florence is home to plenty of attractions that offer fun adventures, scenic views, and photo-friendly spots! Start at Fortezza Medicea (siena), a curiosity-inducing monument that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of San Domenico, enchanting visitors with its stunning appeal. Continue your exploration at Siena Cathedral. This church is one of the city’s most locally renowned spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Del Campo. After exploring the public square, head to the often recommended Tower Of Mangia. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Pubblico Palace, a place of picture-perfect interest in Florence.

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.

Treat yourself to a delightful dinner at Ristorante Buca Mario, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Agricola Toscana? It's another excellent option with a diverse menu. Consider reserving a table at Eataly Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Unwind after your meal by stepping into Gosh*. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Quelo Bar, another top-rated bar in the area.

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

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Day 7

Day 7

  • Florence
  • More

Drive 196 km, 3 hours 17 min

  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Piazza dell'Anfiteatro
  • Guinigi Tower
  • Walls of Lucca
  • More

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

Get ready to discover some of the most iconic wonders in Florence, including a public square, a monument, and a historical landmark. Start your day at Piazza Del Duomo, Pisa. This UNESCO world heritage-designated public square is a wondrous place to see in Florence. Then, wander over to Leaning Tower Of Pisa. If picture-perfect sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Dell'anfiteatro. This romantic 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, Guinigi Tower is a curiosity-inducing spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the enchanting Mura Di Lucca. Take a moment to appreciate the fascinating details of this beloved historical landmark.

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 wonderful meal at Tijuana, a top-rated dining spot in Florence. If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu. You might also want to book a table at The Florence Irish Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Savor another day of unforgettable experiences in Italy!

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Day 8

Day 8

  • Florence
  • Triest
  • More

Drive 414 km, 4 hours 49 min

  • Two Towers
  • Piazza Santo Stefano
  • International Museum and Library of Music
  • More

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. 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.

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the well-known Two Towers, a breathtaking monument in Florence. Next, go to Piazza Santo Stefano.

After visiting Two Towers and Piazza Santo Stefano, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to International Museum And Library Of Music. This photogenic museum offers a unique experience.

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

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.

To truly maximize your evening out, consider visiting Mast after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Urbanis, another bar with an inviting ambiance. Similarly, Coktail Bar Trieste | La Preferita 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!

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Day 9

Day 9

  • Triest - Departure day
  • More
  • Giants' Stairway
  • More

Day 9 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Trieste before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Trieste's best shopping area, Piazza Unità d'Italia. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy. Browse through boutiques to find unique and stylish fashion pieces to take home. When you need a break, visit a cafe and relax with a cup of coffee or tea.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Trieste.

Treat yourself to a delightful dinner at Caffè degli Specchi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria Istriano Of Giobi And Oxa? It's another excellent option with a diverse menu.

You’ll then say farewell to Trieste. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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