Luxury 9-Day Spain Road Trip from Valladolid traveling east to Madrid, and Toledo

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Set off on the ultimate travel extravagance with this 9-day luxury road trip across Spain. Every aspect of your journey is crafted to provide a sophisticated and comfortable experience. Enjoy a holiday where luxury unfolds at every turn in each stop of your adventure in Spain.

Spain 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 Spain. With this perfectly planned vacation itinerary, you will stay 3 nights in Valladolid, 2 nights in Madrid, and 3 nights in Toledo, experiencing the ultimate luxury vacation in Spain.

Finding the perfect luxury lodging is going to make your vacation in Spain feel truly special. The home for your 9-day luxury holiday will be only the most exclusive 5-star hotels in Spain. 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 Spain, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 9-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 Spain.

Throughout your exclusive vacation in Spain, 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 Spain. Here you can find unique souvenirs to preserve the memory of your luxury holiday in Spain.

This exclusive travel plan is designed to include everything you need to have the best vacation in Spain. By booking this luxury holiday package, you can avoid spending hours researching and planning your 9-day road trip in Spain. 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 Spain before and after booking. Our flexible trip planning means you will be able to explore Valladolid, Segovia, Real Sitio de San Ildefonso, Madrid, Toledo, San Lorenzo de El Escorial, and El Escorial 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 Spain.

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

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Day 1

Day 1 – Valladolid - arrival day

  • Valladolid - Arrival day
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  • Plaza Mayor de Valladolid
  • More

Your luxury holiday in Spain begins as soon as you reach the city of Valladolid, where you'll be staying for 2 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

A top pick for your self-guided sightseeing tour today is Plaza Mayor. Previous visitors have rated this square an average of 4.7 out of 5 stars in 6,713 reviews.

Tonight, you will be treated to a stay at one of the best luxury hotels in Valladolid. 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 Valladolid for you, so you can check out the menus and make your reservation in advance.

Make sure to book a table at The other library Café, a popular restaurant in Valladolid. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Valladolid at Café & copas Murmullo, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is ATYPIKAL. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Valladolid tonight.

After your meal, keep the night alive at a bar like The Lost Child Cocktail's Bar, known for its lively atmosphere. Café Bar Alborada is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Monasterio offers an excellent atmosphere for those looking to amp up the evening.

Raise a toast to the start of your 9-day luxury vacation in Spain and look forward to more fantastic days to come!

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Day 2

Day 2 – Valladolid

  • Valladolid
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Drive 9 km, 56 min

  • Museo Nacional de Escultura - Colegio de San Gregorio
  • Cathedral of Valladolid
  • Plaza de Zorrilla
  • Parque Campo Grande
  • More

Day 2 of your luxury road trip in Spain begins and concludes in the city of Valladolid. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Valladolid, where you still have 1 night nights remaining.

Start your sightseeing with a visit to National Sculpture Museum. This art museum is a popular stop on travelers’ itineraries in Valladolid, with an average rating of 4.7 out of 5 stars by 3,935 visitors. Around 145,606 people visit this attraction every year.

Cathedral Of Valladolid is another popular place of interest you can visit today. The average rating of 4.3 out of 5 stars from 5,791 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Plaza De Zorrilla. Visitors have rated this square an average of 4.6 out of 5 stars in 6,590 reviews.

Tren Burra is another unique site you can experience today. This attraction is a park rated an average of 4.3 out of 5 stars in 190 reviews.

Make your way to the fantastic Parque Campo Grande, perhaps the most famous park in Valladolid. This attraction is rated 4.7 out of 5 stars by 15,850 travelers.

Discover a world of culinary delights in Valladolid, 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.

Get ready for an unforgettable culinary journey in Valladolid by reserving a table at Alquimia - Laboratorio. Renowned as a 1-star Michelin restaurant, it offers an exceptional creative, and modern menu. For a different taste experience, head to Trigo, recognized for its delicious modern dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Llantén, a local favorite known for its delightful traditional cuisine in Valladolid. Nestled in the heart of the city, this Bib Gourmand awardee is an ideal choice for discerning traditional foodies seeking culinary excellence.

Keep the evening going at Rugby Bar The Central, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Villa Gin Bar, which offers a similarly pleasant setting and great drinks.

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

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Day 3

Day 3 – Valladolid, Segovia, Real Sitio de San Ildefonso, and Madrid

  • Madrid
  • Segovia
  • San Ildefonso
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Drive 227 km, 3 hours 14 min

  • Alcázar de Segovia
  • Catedral de Segovia
  • Aqueduct of Segovia
  • Royal Palace of La Granja of San Ildefonso
  • More

Wake up to day 3 of your luxury road trip holiday in Spain! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Madrid, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Segovia, and Real Sitio de San Ildefonso.

Embrace the thrill of the open road as you wave goodbye to Valladolid and set your GPS to Segovia. 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 21 min. Upon reaching Segovia, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Make Alcázar Of Segovia your first stop of the day. Previous visitors have rated this alcázar an average of 4.7 out of 5 stars in 49,713 reviews. More than 754,946 people visit this place of interest every year.

Next up, make a stop at Segovia Cathedral. With an average rating of 4.7 out of 5 stars by 18,509 visitors, it's easy to understand why so many people visit this catholic cathedral every year.

Aqueduct Of Segovia is another attraction you can visit on this day of your vacation. This stone bridge has an average rating of 4.8 out of 5 stars by 95,202 visitors.

Embrace the thrill of the open road as you wave goodbye to Segovia and set your GPS to Real Sitio de San Ildefonso. 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 17 min. Upon reaching Real Sitio de San Ildefonso, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Journey into the unknown at Royal Palace Of La Granja Of San Ildefonso, a unique attraction awaiting your visit. This remarkable museum has an average rating of 4.6 out of 5 stars from 19,635 reviews.

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

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

Get ready for an unforgettable culinary journey in Madrid by reserving a table at DiverXO. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Smoked Room, recognized for its delicious contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Paco Roncero, a local favorite known for its delightful creative cuisine in Madrid. Nestled in the heart of the city, this restaurant with 2 Michelin star is an ideal choice for discerning creative foodies seeking culinary excellence.

After your meal, keep the night alive at a bar like Baton Rouge Cocktail Bar, known for its lively atmosphere. Cafe Madrid is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, 1862 Dry Bar offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 4

Day 4 – Madrid

  • Madrid
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Drive 15 km, 1 hour 14 min

  • Santiago Bernabéu Stadium
  • Puerta de Alcalá
  • El Retiro Park
  • Museo Nacional del Prado
  • Museo Nacional Centro de Arte Reina Sofía
  • More

Day 4 of your luxury road trip in Spain begins and concludes in the city of Madrid. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Madrid, where you still have 1 night nights remaining.

Begin your sightseeing with a visit to Santiago Bernabéu Stadium. This extraordinary association football venue is rated an average of 4.6 out of 5 stars by 120,158 visitors.

Next, make your way to Puerta De Alcalá. This top attraction is a triumphal arch with an average rating of 4.7 out of 5 stars by 43,833 visitors.

We also recommend a visit to El Retiro Park. This urban park is rated 4.8 out of 5 stars by 162,386 travelers.

If you’re keen to keep exploring, visit Museo Del Prado. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 98,929 travelers. Around 3,497,345 people come to experience this place of interest every year.

Today is also your chance to spend some time at Museo Nacional Centro De Arte Reina Sofía. This art museum is rated an average of 4.5 out of 5 stars by 46,855 travelers. It’s estimated that 1 person visit this fantastic attraction every year.

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

Dine in style at La Mi Venta, a top recommendation for dinner tonight. Or, for a change of pace, Mas Al Sur boasts a menu that's sure to impress. Also, be sure to check out Prada a Tope Madrid. Known as a local hotspot, it’s a great choice for tonight in Madrid.

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

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Day 5

Day 5 – Madrid, and Toledo

  • Toledo
  • Madrid
  • More

Drive 87 km, 1 hour 48 min

  • Plaza Mayor
  • San Miguel Market
  • Royal Palace of Madrid
  • Plaza de España
  • Casa de Campo
  • More

Wake up to day 5 of your luxury holiday in Spain! Remember to have a hearty breakfast because today will be filled with memorable adventures in Madrid. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Be one of the day’s first visitors at Main Square. This square is rated an average of 4.6 out of 5 stars by 152,388 visitors.

When you’re finished at Main Square, head to Market Of San Miguel. This one-of-a-kind building is rated an average of 4.4 out of 5 stars in 106,296 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Royal Palace Of Madrid. This royal palace is rated an average of 4.6 out of 5 stars by 77,471 visitors.

If you’re keen to explore more, then consider a visit to Plaza De España. This square is a much-appreciated attraction with an average rating of 4.4 out of 5 stars from 98,199 visitors.

To round off your sightseeing experience, make your way to Casa De Campo. This famous park is rated an average of 4.5 out of 5 stars by 50,826 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Toledo. 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 Toledo.

Experience a symphony of flavors at Iván Cerdeño in Toledo by securing a reservation in advance. Renowned for its 2-star Michelin distinction, Iván Cerdeño delights its guests with its exceptional variety of meals showcasing delicious modern cuisine. Or, if you're feeling adventurous, why not try Tobiko Restaurante? It's another excellent option with a diverse menu.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Buca Bar, known for its inviting atmosphere. Pub "o'briens" is another great option if you’re looking for a place to get the night started. Similarly, Terraza Miradero provides a great setting to enjoy the night away.

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

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Day 6

Day 6 – Toledo

  • Toledo
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Drive 8 km, 1 hour 8 min

  • Mirador del Valle
  • Alcantara Bridge
  • Puerta de Bisagra
  • Monasterio de San Juan de los Reyes
  • San Martin's Bridge
  • More

Day 6 of your luxury road trip in Spain begins and concludes in the city of Toledo. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Toledo, where you still have 2 nights nights remaining.

An excellent attraction to start your day with is Mirador Del Valle. This landmark is rated an average of 4.8 out of 5 stars in 10,058 reviews.

Continue your journey at Alcantara Bridge. This sightseeing destination is rated 4.7 out of 5 stars by 8,836 travelers from near and far.

Toledo is also the home of Puerta De Bisagra. This city gate has an average rating of 4.7 out of 5 stars from 9,260 visitors.

You can continue your self-guided sightseeing tour at Monasterio De San Juan De Los Reyes, Toledo. Rated 4.6 out of 5 stars by 6,783 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on San Martin's Bridge. With an average rating of 4.7 out of 5 stars from 10,516 reviews, it’s hard to refuse the opportunity to see this point of interest.

After a long day of discovering the unique quirks of Spain, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Toledo so you can check out the menus and make advance reservations.

Enjoy a lovely meal at Restaurante Taberna El Gallo Toledo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Clandestina is another top choice with a popular menu. You could also check for a table at Restaurante "El Cobertizo". As an establishment that gains consistently high praises from customers, it’s an ideal choice in Toledo tonight.

Celebrate another great day of your luxury holiday in Spain 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 7

Day 7 – Toledo

  • Toledo
  • More

Drive 1 km, 21 min

  • Alcázar de Toledo
  • Army Museum
  • Zocodover
  • Santa Iglesia Catedral Primada de Toledo
  • More

Day 7 of your luxury road trip in Spain begins and concludes in the city of Toledo. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Toledo, where you still have 1 night nights remaining.

When you're ready to see some sights, Alcázar Of Toledo is a great place to start. This alcázar is rated an average of 4.6 out of 5 stars by 30,193 visitors.

Another popular attraction you can visit today is Army Museum. This military museum has an average rating of 4.5 out of 5 stars from 5,537 travelers.

We also recommend a stop at Zocodover. The sightseeing destination has been rated an average of 4.5 out of 5 stars by 19,930 visitors.

If you're keen to explore more, consider visiting Santa Iglesia Catedral Primada De Toledo. This church is a popular attraction with an average rating of 4.7 out of 5 stars from 27,938 reviews.

After a day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Toledo. Savor the local cuisine and relax as you recount the day's experiences.

Treat yourself to a delicious dinner at Jacaranda Bar, an excellent option for tonight's dining. Looking for something different? Taberna el Botero offers a tantalizing alternative with its diverse menu. And don’t miss La Orza. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Toledo.

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

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Day 8

Day 8 – Toledo, San Lorenzo de El Escorial, El Escorial, Puerto de Navacerrada, and Valladolid

  • Valladolid
  • San Lorenzo de El Escorial
  • El Escorial
  • More

Drive 302 km, 3 hours 56 min

  • Royal Seat of San Lorenzo de El Escorial
  • More

On day 8 of your luxury holiday in Spain, your road trip route will take you exploring the best of San Lorenzo de El Escorial, El Escorial, and Puerto de Navacerrada. The day's journey will conclude in Valladolid, 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 Spain.

When you’ve had your share of Toledo, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of San Lorenzo de El Escorial. Your travel time is around 1 hour 29 min.

A top pick for your self-guided sightseeing tour today is Royal Monastery Of San Lorenzo De El Escorial. Previous visitors have rated this monastery an average of 4.7 out of 5 stars in 25,732 reviews.

Frailes Garden is a local recommendation that you also can pay a visit today. This park is rated an average of 4.6 out of 5 stars in 2,686 reviews.

After soaking in San Lorenzo de El Escorial’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: El Escorial. Expect your car journey to take a minimum of 4 min. When you arrive in El Escorial, it's time to take a break from the road.

An excellent attraction to start your day with is Casita Del Príncipe. This park is rated an average of 4.1 out of 5 stars in 2,248 reviews.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Puerto de Navacerrada. This drive usually takes around 36 min, without any stops or traffic disruptions.

Start your sightseeing with a visit to “puerto De Navacerrada” Ski Station. This park is rated an average of 4.4 out of 5 stars from 12,637 visitors.

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

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

Treat yourself to a delicious dinner at La Parrilla De San Lorenzo, an excellent option for tonight's dining. Looking for something different? Restaurante Pide por esa Boquita offers a tantalizing alternative with its diverse menu. And don’t miss Villa Paramesa. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Valladolid.

Celebrate another great day of your luxury holiday in Spain 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 9

Day 9 – Valladolid - departure day

  • Valladolid - Departure day
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  • Parque de las Moreras
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Today is the last day of your 9-day luxury holiday in Spain and it’s soon time to start your journey home. This is your chance to get one last glimpse of Valladolid before saying goodbye.

Make the most of your final day in Spain by visiting Valladolid’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Spain.

Make the most of what's left of your luxury vacation and head out to the stunning Parque Y Playa De Las Moreras. This extraordinary park and attraction is rated an average of 4.4 out of 5 stars in 3,395 reviews, and is an excellent choice for your last sightseeing in Valladolid.

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

You will then say farewell to Valladolid 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 Spain in your luggage!

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