7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Venice and Florence

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Milan Cathedral, Duomo di Milano, and Piazza Duomo square in the Milan city center, Italy
Photo of Arch of Peace, or Arco della Pace, city gate in the centre of the Old Town of Milan in the sunny day, Lombardia, Italy.
7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Venice and Florence
7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Venice and Florence
7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Venice and Florence
7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Venice and Florence
7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Venice and Florence
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Escape the ordinary with this exciting 7-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 2 nights in Milan, 2 nights in Venice, and 2 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 you covered.

Upon arriving in Milan, 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.

As you hit the open road and drive through Milan, Venice, Florence, Siena, Colle di Val d'Elsa, and Parma, 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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Day1

Day 1

  • Milan - Arrival day
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  • Sempione Park
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Say hello to Milan! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Milan for 1 night before you continue your adventure!

Milan 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 Parco Sempione. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Milan. 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 Milan, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Hotel Morfeo Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Contraste, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Galles Milano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Nottingham Forest, a well-loved spot among locals and tourists. Or, head to Armani/bamboo Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Mag Cafe, another top-rated place in the area.

Raise a toast to the start of your 7-day road trip in Italy!

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Day2

Day 2

  • Milan
  • Venice
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Drive 276 km, 3 hours 43 min

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

Your itinerary for day 2 of your road trip in Italy includes 1 stop and features some of the highlights of Venice. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll 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 3 hours 1 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 UNESCO world heritage-listed 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, a visually striking church.

Nearby, you will also find Piazza San Marco. This timeless public square is a top place to see in the area. Lastly, head to Rialto Bridge, a history-steeped historical landmark 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.

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

Dine in style at Bauer Hotel, a top recommendation for dinner tonight. Or, for a change of pace, L'Osteria Le Guglie boasts a menu that's sure to impress. Also, be sure to check out Corner Pub. Known as a local hotspot, it’s a great 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 Al Parlamento, a well-loved spot among locals and tourists. Or, head to The Caffe Rosso. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Adagio, another top-rated place in the area.

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

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Day3

Day 3

  • Venice
  • More

Drive 4 km, 1 hour 4 min

  • Santa Maria della Salute
  • Peggy Guggenheim Collection
  • Teatro La Fenice
  • Palazzo Contarini del Bovolo
  • Basilica S.Maria Gloriosa dei Frari
  • Santa Croce
  • More

Day 3 offers an itinerary packed with the best things to see in Milan. You’ll stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Don’t miss Santa Croce 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.

Check out the up-and-coming church, Santa Maria Della Salute. Afterward, continue to Peggy Guggenheim Collection, an art gallery every traveler should visit. As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Teatro La Fenice. This notable opera house is an essential stop. Following that, head to Palazzo Contarini Del Bovolo, another must-visit site that will enhance your experience. Don’t forget to stop by Santa Maria Gloriosa Dei Frari, a locally appreciated church in the city.

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.

Make sure to reserve a table at Generator Venice, 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 Nevodi, 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 Ristorante La Piazza, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Il Mercante, which offers the perfect atmosphere for a night out. Moreover, The Irish Pub Venezia is another popular option for a drink or two. Likewise, Ai Stagneri also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

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Day4

Day 4

  • Venice
  • Florence
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Drive 259 km, 3 hours 18 min

  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • Piazza della Repubblica
  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • More

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

Florence’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Venice behind. This drive usually takes around 2 hours 52 min. Florence welcomes you with a multitude of unique vacation experiences.

Spend your afternoon discovering Galleria Dell'accademia, a notable art gallery known for its history-steeped features. Next, continue your sightseeing at Cathedral Of Santa Maria Del Fiore, an extraordinary 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 Piazza Della Repubblica and uncover the details of this romantic public square. Make sure to also explore Ponte Vecchio, a wondrous historical landmark. For your last stop, consider Uffizi Gallery, a history-steeped art gallery that many travelers find worth the detour.

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 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.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

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Day5

Day 5

  • Florence
  • Siena
  • Colle di Val d'Elsa
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Drive 160 km, 3 hours 10 min

  • Porta Pispini
  • piazza del Campo
  • Siena Cathedral
  • Basilica of San Domenico
  • Fortezza Medicea
  • The Diborrato Waterfall
  • More

On day 5 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Siena and Colle di Val d'Elsa to the fullest today with this curated day itinerary.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Siena. 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 1 hour 9 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Spend your afternoon discovering Porta Pispini, an increasingly popular historical landmark known for its culturally significant features. Next, continue your sightseeing at Piazza Del Campo, an impressive public square.

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 Siena Cathedral and uncover the details of this enchanting church. Make sure to also explore Basilica Of San Domenico, an up-and-coming church. For your last stop, consider Fortezza Medicea (siena), a culturally significant monument that many travelers find worth the detour.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Colle di Val d'Elsa. This drive usually takes around 23 min.

Savor the day by heading to The Diborrato Waterfall, an up-and-coming waterfall that draws visitors from near and far.

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. If you are looking to dine at a popular restaurant in Florence, 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.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day6

Day 6

  • Florence
  • Parma
  • Milan
  • More

Drive 315 km, 3 hours 56 min

  • Galleria nazionale di Parma
  • Palazzo della Pilotta
  • Teatro Regio
  • Parma Cathedral
  • 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. Parma are on today's agenda. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Set your GPS to Parma and hit the road. Expect a journey of approximately 2 hours 9 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Parma beckons with new experiences!

When you're ready for some sights, head to Galleria Nazionale Di Parma, an increasingly popular art gallery in Parma. Explore its history-steeped features at your own pace before you continue your journey to your next attraction, Palazzo Della Pilotta. This often recommended palace is a top recommendation in the area.

When you’re ready to explore more, Teatro Regio is an excellent choice. Spend some time discovering what some claim to be the most history-steeped opera house in the region. Next, continue your sightseeing at the underrated Parma Cathedral and discover what makes this church unique.

At the end of the day, you will drive to Milan, 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 Milan, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Dessert Bar Milano, a highly-rated dining destination in Milan. If you're eager to try something different, consider Radisson Blu Hotel Milan, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

Continue your evening by exploring the vibrant nightlife scene at Kilburn Cocktail Bar Milano, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Frida, a bar that offers unique local touches. Likewise, The Friends Pub Milano provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences in Italy!

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Day7

Day 7

  • Milan - Departure day
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  • Duomo di Milano
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Day 7 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Milan 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 Duomo Di Milano Museum, a visually striking church before you head out.

Take advantage of your accommodation's proximity to Milan’s shopping district for some last-minute bargain hunting. Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones. Discover boutiques offering an array of stylish fashion choices. Take a break with a cup of coffee or tea while savoring the local vibe in a coffee shop.

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

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu.

You’ll then say farewell to Milan. 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.
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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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