Luxury 4-Day Italy Road Trip from Pisa to Siena and surrounding area

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Description

Escape for the holiday of a lifetime with this 4-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 Pisa, and 1 night in Siena, 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 4-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 4-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 4-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 Pisa, Siena, Levanto, Corniglia, and La Spezia 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 – Pisa - arrival day

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

Make Knights' Square one of your first sightseeing stops in Pisa. Rated an average of 4.5 out of 5 stars by 9,051 travelers, a visit to this local attraction makes for a great introduction to the area.

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

After a long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Pisa for you, so you can check out the menus and make your reservation in advance.

Treat yourself to a delightful dinner at Ristorante Capodimonte Pisa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Baribaldi Pisa? It's another excellent option with a diverse menu. Consider reserving a table at Restaurant -Pizzeria Il Mio Capriccio as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

Explore the vibrant nightlife at Jeffer Cocktails & Friends after your meal, a hub for lively evenings and memorable moments. Or, head to Le Parisien Wine Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Las Volta Cocktailbar is perfect for those looking to extend their night with a touch of local flavor.

Raise a toast to the start of your 4-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Pisa, Cascine Vecchie, and Siena

  • Siena
  • Pisa
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Drive 136 km, 2 hours 17 min

  • Palazzo Blu
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Pisa Cathedral
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
  • More

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Pisa, and Cascine Vecchie. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Palazzo Blu. This art museum is a popular stop on travelers’ itineraries in Pisa, with an average rating of 4.5 out of 5 stars by 4,244 visitors. Around 37,457 people visit this attraction every year.

Piazza Del Duomo, Pisa is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 104,550 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Leaning Tower Of Pisa. Visitors have rated this bell tower an average of 4.7 out of 5 stars in 116,882 reviews. Leaning Tower Of Pisa receives around 3,200,000 visitors every year.

Pisa Cathedral is another unique site you can experience today. This attraction is a cathedral rated an average of 4.8 out of 5 stars in 8,361 reviews.

Cascine Vecchie’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 9 min. Cascine Vecchie welcomes you with a multitude of unique vacation experiences.

Begin your sightseeing with a visit to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This extraordinary park is rated an average of 4.4 out of 5 stars by 9,632 visitors.

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

Discover a world of culinary delights in Siena, 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.

Enjoy a delicious meal at Antica Trattoria Papei, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Quattro Venti, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

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

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Day 3

Day 3 – Siena, Levanto, Corniglia, La Spezia, and Pisa

  • Pisa
  • Levanto
  • Corniglia
  • La Spezia
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Drive 370 km, 5 hours

  • Spiaggia Levanto
  • Cinque Terre National Park
  • Giardini Pubblici
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Wake up to day 3 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 Pisa, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Levanto, Corniglia, and La Spezia.

Set your GPS to Levanto and hit the road. Expect a journey of approximately 2 hours 46 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Levanto beckons with new experiences!

Journey into the unknown at Spiaggia Levanto, a unique attraction awaiting your visit. This remarkable point of interest has an average rating of 4.3 out of 5 stars from 4,950 reviews.

When you’ve had your share of Levanto, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Corniglia. Your travel time is around 32 min.

When you’re ready for some sightseeing, make your way to Cinque Terre National Park. This much-appreciated park is rated 4.7 out of 5 stars in 43,526 reviews.

When you’ve had your share of Corniglia, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of La Spezia. Your travel time is around 35 min.

Drop by the renowned Giardini Pubblici. This popular park has been rated an average of 4.1 out of 5 stars by 2,364 visitors.

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.

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

Dine in style at Ristorante alle Bandierine, a top recommendation for dinner tonight. Or, for a change of pace, Barrique Cocktail And Bistrot boasts a menu that's sure to impress. Also, be sure to check out Filter Coffee Lab. Known as a local hotspot, it’s a great choice for tonight in Pisa.

To truly maximize your evening out, consider visiting Bar Mocambo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Tree, another bar with an inviting ambiance. Similarly, Chupiteria also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

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Day 4

Day 4 – Pisa - departure day

  • Pisa - Departure day
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Today is the last day of your 4-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 Pisa before saying goodbye.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Pisa's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

Make the most of what's left of your luxury vacation and head out to the stunning “tuttomondo” (keith Haring). This extraordinary sightseeing destination and attraction is rated an average of 4.6 out of 5 stars in 1,937 reviews, and is an excellent choice for your last sightseeing in Pisa.

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

Have a fantastic dining experience at Sud, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Offers an enticing alternative with its varied menu.

You will then say farewell to Pisa 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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