9-Day Italy Self-Drive Road Trip With Itinerary from Venice to Trieste, Florence, and Milan and surrounding area

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Escape the ordinary with this exciting 9-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 3 nights in Venice, 3 nights in Trieste, 1 night in Florence, and 1 night in Milan. 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 you covered.

Upon arriving in Venice, 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 Duomo Di Milano Museum, learn more about the unique Ponte Vecchio, and immerse yourself in the vibrant atmosphere of Leaning Tower Of Pisa.

As you hit the open road and drive through Venice, Trieste, Miramare / Miramar, Padua, Florence, Pisa, and Milan, 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, accommodations, 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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Driver’s age is 30 - 65
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Pick-up: 10:00
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Day 1

Day 1

  • Venice - Arrival day
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  • Rialto Bridge
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Your road trip adventure in Italy begins as soon as you reach Venice and pick up your car. You’ll stay here for 2 nights and explore what to see in Venice, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Venice 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 Rialto Bridge, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Venice. Make yourself at home and unwind before heading out again.

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

Enjoy a lovely dining experience at Bauer Hotel, a popular restaurant in Venice. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Venice at L'Osteria Le Guglie, 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 Corner Pub. It’s yet another ideal choice to enhance your time in Venice tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Al Parlamento stands out as an excellent choice for a post-dinner cocktail. Alternatively, The Caffe Rosso offers an ideal atmosphere to enjoy the pleasures of the night. Adagio is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 2

Day 2

  • Venice
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Drive 1 km, 22 min

  • Piazza San Marco
  • St Mark's Campanile
  • St Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • More

Day 2 offers an itinerary packed with the best things to see in Venice. You’ll stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Piazza San Marco brings Venice's character to life. This romantic public square is a highlight of any visit in the city. Then, enjoy St Mark's Campanile, another UNESCO world heritage-listed attraction that never fails to captivate visitors. Next, head over to St Mark's Basilica, one of the city’s most well-known attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Doge's Palace. This romantic palace is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Bridge Of Sighs, a locally renowned monument, and take a stroll around the area.

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.

Bring home unique finds from Venice's bustling shopping hub, Rialto Market. Enjoy a leisurely exploration of unique stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Rialto Market offers plenty of options, including primary services, unique landmarks, and community events.

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

Enjoy an outstanding dining experience at Local, a 1-star Michelin restaurant offering an exceptional contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 1-star Michelin-awardee, Wistèria, known for its delicious contemporary and venetian cuisine. Another highly-recommended place to eat in Venice is Quadri, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious modern menu.

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.

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

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Day 3

Day 3

  • Venice
  • Triest
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Drive 160 km, 2 hours 21 min

  • Palazzo Contarini del Bovolo
  • Teatro La Fenice
  • Peggy Guggenheim Collection
  • Santa Maria della Salute
  • More

Experience an unparalleled adventure on day 3 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 Trieste, where will spend 3 nights.

Experience Palazzo Contarini Del Bovolo, a locally renowned palace in the city. Then, head to Teatro La Fenice and soak in the ambiance of this picture-perfect opera house.

There are many interesting places to see in Venice, and when you are ready for more, go to Peggy Guggenheim Collection. This is one of the city’s most captivating remarkable spots of interest. After exploring the art gallery, visit the increasingly popular Santa Maria Della Salute.

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

Trieste 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 Trieste.

Begin your culinary exploration in Trieste by securing a reservation at Harry's Piccolo. This renowned restaurant holds 2 Michelin star and offers an exceptional menu of creative cuisine. Or, for a change of pace, Caffè Tommaseo boasts a menu that's sure to impress.

Following your dinner, dive into the local bar culture at Bar G. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar X, the perfect place for those looking to experience the best of the nightlife. Similarly, Antico Caffè Torinese provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 4

Day 4

  • Triest
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Drive 3 km, 47 min

  • Arco di Riccardo
  • Unity of Italy Square
  • Piazza della Borsa
  • canale ponterosso trieste
  • Molo Audace
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Day 4 of your road trip will take you to the best attractions Trieste has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Trieste.

Make a stop at Arco Di Riccardo. This curiosity-inducing archeological site is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Unità D'italia located in Trieste for another exciting encounter.

Next, immerse yourself in the setting of Piazza Della Borsa. Its romantic features will captivate you. After the public square, continue your tour of the city with a visit to Canale Ponterosso Trieste. Visitors usually appreciate the romantic features of this street. Next up is Molo Audace, a highly recommended pier.

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.

Trieste 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 Trieste.

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

If you’re not ready to end the night just yet, Mast offers a perfect venue to relax and savor a drink. Similarly, Urbanis is well-suited for those looking to unwind in a social setting. Coktail Bar Trieste | La Preferita 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!

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Day 5

Day 5

  • Triest
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Drive 20 km, 55 min

  • Miramare Castle
  • Science Center Scientific Imaginary Trieste
  • Civico museo del Castello di San Giusto
  • Cattedrale di San Giusto Martire
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On day 5 of your road trip, you’ll start and end your day in Trieste, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Miramare / Miramar and Trieste.

Awaiting your discovery is the interesting Miramare Castle, a respected castle in Trieste. Next, go to Science Center Scientific Imaginary Trieste.

After visiting Miramare Castle and Science Center Scientific Imaginary Trieste, have a stroll along Trieste's streets and take in the local charm. Continue your sightseeing by heading to Civico Museo Del Castello Di San Giusto. This enchanting castle offers a unique experience. Cattedrale Di San Giusto Martire is another noteworthy attraction worthwhile a visit.

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

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.

Treat yourself to a wonderful meal at Caffè degli Specchi, a top-rated dining spot in Trieste. If you're in the mood for something new, try Osteria Istriano Of Giobi And Oxa, another premier location with a delectable menu. You might also want to book a table at Chimera di Bacco. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Trieste.

To truly maximize your evening out, consider visiting "life" New Bar Torinese Snc after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to White Cafe, another bar with an inviting ambiance. Similarly, Café James Joyce also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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.

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Day 6

Day 6

  • Triest
  • Florence
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Drive 420 km, 5 hours 18 min

  • Scrovegni Chapel
  • The Basilica of St Anthony
  • Prato della Valle
  • More

On day 6 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Padua are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Make time for Scrovegni Chapel, a locally renowned church that is worthwhile a visit in the city. Nearby, you’ll find The Basilica Of St. Anthony, enchanting visitors with its culturally significant appeal. Continue your exploration at Prato Della Valle. This public square is one of the city’s most well-known spots.

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

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 7

Day 7

  • Florence
  • Milan
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Drive 370 km, 5 hours 3 min

  • Ponte Vecchio
  • piazzale Michelangelo
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
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Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Florence and Pisa. At the end of the day, you’ll unwind at one of the finest accommodations in Milan, where you'll spend 1 night.

Your adventure in Florence is only getting started when you visit Ponte Vecchio, a wondrous local hot spot. Another notable attraction to explore is Piazzale Michelangelo. This famous observation deck is known for its respected 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 Leaning Tower Of Pisa. This culturally significant monument offers a fascinating experience that many visitors find memorable. Piazza Del Duomo, Pisa is also worth visiting.

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

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

Set out on a gastronomic journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. For a different taste, head over to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Il Luogo Aimo e Nadia, a highly rated local gem known for its exquisite italian contemporary and modern menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. Known for great service, it’s a fantastic choice for tonight in Milan.

Round off your dining experience by visiting Nottingham Forest, a prime location for a drink. Alternatively, explore the distinctive characteristics of Armani/bamboo Bar, a bar catering to every mood and preference. Mag Cafe likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 8

Day 8

  • Milan
  • Venice
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Drive 267 km, 3 hours 26 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • La Scala
  • Castello Sforzesco
  • Sempione Park
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Your itinerary for day 8 of your road trip in Italy includes 1 stop and features some of the highlights of Milan. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 1 night.

Duomo Di Milano Museum is perfect for a self-paced visit during the day. This visually striking church is sure to impress. Next on your list is Galleria Vittorio Emanuele Ii, another must-visit landmark and extraordinary shopping mall renowned for its visually striking features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to La Scala. This romantic opera house is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Sforzesco Castle Art Library, an extraordinary castle. Nearby, you'll also find Parco Sempione, ready to add charm to your journey.

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

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.

Make sure to reserve a table at Osteria Alla Staffa, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bistrot de Venise, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corte Sconta, a hidden gem nestled in Venice. 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 Dolce Vita Venezia, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tarnowska's American Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar All'angolo 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 Italy.

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Day 9

Day 9

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

If you're up for some more sightseeing, we recommend visiting Venetian Arsenal, a breathtaking historical landmark before you head out.

For a last-minute shopping spree in Venice, Calle Larga XXII Marzo is nearby. Enjoy a variety of retail stores, dining options, and essential services in one convenient location. Explore high-end stores offering an exquisite selection of luxury items.

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

If you're eager to try something different, consider Trattoria Al Gazzettino, another top spot with a tantalizing menu.

You’ll then say farewell to Venice. 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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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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