Luxury 5-Day Italy Road Trip from Venice traveling south to Florence, and Pisa

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Description

Escape for the holiday of a lifetime with this 5-day luxury road trip in Italy!

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned vacation itinerary, you will stay 2 nights in Venice, 1 night in Florence, and 1 night in Pisa, experiencing the ultimate luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 5-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.

Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 5-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.

Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. Here you can find unique souvenirs to preserve the memory of your luxury holiday in Italy.

This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 5-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.

To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Venice, Florence, Pisa, and Bologna at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best flights, activities, tours, and hotels in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your luxury holiday in Italy today!

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Day 1

Day 1 – Venice - arrival day

  • Venice - Arrival day
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  • Teatro La Fenice
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Your luxury holiday in Italy begins as soon as you reach the city of Venice, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

An excellent attraction to start your day with is Teatro La Fenice. This opera house is rated an average of 4.7 out of 5 stars in 10,677 reviews.

Tonight, you will be treated to a stay at one of the best luxury hotels in Venice. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Venice.

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

If you’re not ready to end the night just yet, Al Parlamento offers a perfect venue to relax and savor a drink. Similarly, Adagio is well-suited for those looking to unwind in a social setting. Il Mercante is another excellent spot to enjoy a nightcap after a delightful meal.

Raise a toast to the start of your 5-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Venice, and Florence

  • Florence
  • Venice
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Drive 259 km, 3 hours 9 min

  • St. Mark's Square
  • Saint Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
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On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Venice. The day's journey will conclude in Florence, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

A top pick for your self-guided sightseeing tour today is Piazza San Marco. Previous visitors have rated this square an average of 4.7 out of 5 stars in 152,982 reviews.

St Mark's Basilica is a local recommendation that you also can pay a visit today. This cathedral is rated an average of 4.7 out of 5 stars in 18,439 reviews.

Another attraction you won't want to miss is Doge's Palace. This palace is rated an average of 4.7 out of 5 stars in 24,775 reviews. Every year, around 318,104 travelers visit this site to discover its unique features.

Bridge Of Sighs is another outstanding experience in Venice. Around 18,223 travelers have rated this footbridge an average of 4.6 out of 5 stars.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Florence.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative, and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary, and international cuisine in the city.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Reminisce about your day, look through photos, and prepare for another great day to come! Your stress-free luxury holiday in Italy has plenty more in store for you.

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Day 3

Day 3 – Florence, and Pisa

  • Pisa
  • Florence
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Drive 88 km, 1 hour 56 min

  • Piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Uffizi Gallery
  • Piazzale Michelangelo
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Wake up to day 3 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Make Piazza Della Signoria your first stop of the day. Previous visitors have rated this square an average of 4.8 out of 5 stars in 66,956 reviews.

Next up, make a stop at Cathedral Of Santa Maria Del Fiore. With an average rating of 4.8 out of 5 stars by 76,359 visitors, it's easy to understand why so many people visit this church every year.

Ponte Vecchio is another attraction you can visit on this day of your vacation. This deck arch bridge has an average rating of 4.7 out of 5 stars by 118,099 visitors.

When you’re finished at Ponte Vecchio, the perfect next stop is Uffizi Gallery. This national museum is rated an average of 4.7 out of 5 stars in 61,794 reviews. Uffizi Gallery attracts approximately 2,011,219 visitors annually.

If you’re keen to explore even more, then consider a visit to Piazzale Michelangelo. This square is a top place to visit, with a rating of 4.8 out of 5 stars from 77,744 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Pisa. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Discover a world of culinary delights in Pisa, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Baribaldi Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Restaurant -Pizzeria Il Mio Capriccio, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Jeffer Cocktails & Friends stands out as an excellent choice for a post-dinner cocktail. Alternatively, Le Parisien Wine Bar offers an ideal atmosphere to enjoy the pleasures of the night. Las Volta Cocktailbar is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to another amazing day of your luxury holiday in Florence, Italy and seize the opportunity to celebrate.

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Day 4

Day 4 – Pisa, Bologna, and Venice

  • Venice
  • Pisa
  • Bologna
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Drive 331 km, 3 hours 53 min

  • Leaning Tower of Pisa
  • Piazza del Duomo
  • Cattedrale di Pisa
  • Museo Ducati
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Wake up to day 4 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Venice, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Pisa, and Bologna.

Drop by the renowned Leaning Tower Of Pisa. This popular bell tower has been rated an average of 4.7 out of 5 stars by 116,882 visitors. Based on recent data, this attraction is visited by more than 3,200,000 travelers every year.

Another unforgettable place to experience is Piazza Del Duomo, Pisa. Rated 4.7 out of 5 stars by 104,550 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Pisa Cathedral. This cathedral has been rated an average of 4.8 out of 5 stars in 8,361 reviews.

Set your GPS to Bologna and hit the road. Expect a journey of approximately 1 hour 50 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Bologna beckons with new experiences!

An excellent attraction to start your day with is Ducati Museum. This industry museum typically receives around 7,600 visitors every year and is rated an average of 4.5 out of 5 stars in 4,028 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Venice. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

After exploring the unique sights of Italy, savor a delicious meal or get refreshed with a drink. We’ve gathered the most recommended restaurants and bars in the city of Venice for you so you can browse their menus in advance and make a reservation.

Prepare for an extraordinary culinary adventure in Venice by booking a table at Local, a 1-star Michelin restaurant that boasts an exceptional contemporary menu. For a different flavor experience, head to Wistèria, renowned for its delectable contemporary, and venetian dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Quadri, a local gem known for its delightful modern cuisine in Venice. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Explore the vibrant nightlife at The Irish Pub Venezia after your meal, a hub for lively evenings and memorable moments. Or, head to Dolce Vita Venezia for a great selection of flavorful drinks and a charming setting. Furthermore, Devils Forest Pub is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass and relax after another big day of your luxury holiday in Italy!

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Day 5

Day 5 – Venice - departure day

  • Venice - Departure day
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  • Rialto Bridge
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Today is the last day of your 5-day luxury holiday in Italy and it’s soon time to start your journey home. This is your chance to get one last glimpse of Venice before saying goodbye.

Maximize your last day in Italy and go on a shopping spree in Venice’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Rialto Bridge. This extraordinary stone bridge and attraction is rated an average of 4.7 out of 5 stars in 141,666 reviews, and is an excellent choice for your last sightseeing in Venice.

Treat yourself to a final feast. Savor the unique flavors of Venice one last time before you head to the airport.

Treat yourself to a delicious dinner at La Palanca, an excellent option for tonight's dining. Looking for something different? Farini offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Dona Onesta.

You will then say farewell to Venice and begin your journey home. We wish you safe travels and a warm welcome home, with unforgettable memories and incredible photos from your luxury holiday in Italy in your luggage!

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