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

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Experience travel that redefines comfort and elegance with this 9-day luxury road trip in Spain. Witness Spain's awe-inspiring scenery, delight in the finest culinary offerings, and enjoy the ultimate comfort in top-tier accommodations.

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 4 nights in Madrid, 2 nights in Toledo, 1 night in Avila, and 1 night in Valladolid, 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 Madrid, Toledo, Avila, Salamanca, Valladolid, Segovia, and Real Sitio de San Ildefonso 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 – Madrid - arrival day

  • Madrid - Arrival day
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  • Plaza de España
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Your luxury holiday in Spain begins as soon as you reach the city of Madrid, where you'll be staying for 3 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Start your sightseeing with a visit to Plaza De España. This square is rated an average of 4.4 out of 5 stars from 98,199 visitors.

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

After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Madrid. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Treat yourself to a wonderful meal at El miniBAR, a top-rated dining spot in Madrid. If you're in the mood for something new, try Restaurante De María - Felíx Boix, another premier location with a delectable menu. You might also want to book a table at Areia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Madrid.

After enjoying a fulfilling meal, continue your evening at Baton Rouge Cocktail Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Cafe Madrid offers a welcoming atmosphere for easing into the nightlife. Similarly, 1862 Dry Bar provides an excellent environment for a relaxed and enjoyable 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 – Madrid

  • Madrid
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Drive 15 km, 1 hour 6 min

  • Palacio de Cristal
  • El Retiro Park
  • Great Pond of El Retiro
  • Puerta de Alcalá
  • Santiago Bernabéu Stadium
  • More

Day 2 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 2 nights nights remaining.

A top pick for your self-guided sightseeing tour today is Crystal Palace. Previous visitors have rated this building an average of 4.6 out of 5 stars in 39,270 reviews.

El Retiro Park is a local recommendation that you also can pay a visit today. This urban park is rated an average of 4.8 out of 5 stars in 162,386 reviews.

Another attraction you won't want to miss is Great Pond Of El Retiro. This park is rated an average of 4.7 out of 5 stars in 22,242 reviews.

Puerta De Alcalá is another outstanding experience in Madrid. Around 43,833 travelers have rated this triumphal arch an average of 4.7 out of 5 stars.

If you long for more, Santiago Bernabéu Stadium is not far away. This association football venue is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.6 out of 5 stars in 120,158 reviews.

After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Madrid. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Begin your culinary exploration in Madrid by securing a reservation at DiverXO. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Smoked Room, celebrated for its delectable contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Paco Roncero, a top local spot known for its tantalizing creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

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 3

Day 3 – Madrid

  • Madrid
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Drive 19 km, 1 hour 26 min

  • Museo Nacional Centro de Arte Reina Sofía
  • Catedral de la Almudena
  • Royal Palace of Madrid
  • Temple of Debod
  • Casa de Campo
  • More

Day 3 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.

Drop by the renowned Museo Nacional Centro De Arte Reina Sofía. This popular art museum has been rated an average of 4.5 out of 5 stars by 46,855 visitors. Based on recent data, this attraction is visited by more than 1 traveler every year.

Another unforgettable place to experience is Almudena Cathedral. Rated 4.6 out of 5 stars by 19,842 visitors, this catholic cathedral deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Royal Palace Of Madrid. This royal palace has been rated an average of 4.6 out of 5 stars in 77,471 reviews.

Another favorite attraction in the area is Temple Of Debod. This egyptian temple and popular place of interest enjoys a rating of 4.4 out of 5 stars from 44,446 local and international travelers.

If you’re keen to explore even more, then consider a visit to Casa De Campo. With an average rating of 4.5 out of 5 stars from 50,826 travelers, this park is an attraction many avid travelers highly recommend visiting while in Madrid.

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

Make sure to reserve a table at BiBo Dani García, an iconic dining spot in Madrid. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Malacatín, a popular restaurant in Madrid. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Pum Pum Café, a hidden gem nestled in Madrid. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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Day 4

Day 4 – Madrid, and Toledo

  • Toledo
  • Madrid
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Drive 76 km, 1 hour 34 min

  • Plaza Mayor
  • San Miguel Market
  • Círculo de Bellas Artes
  • Thyssen-Bornemisza Museum
  • Museo Nacional del Prado
  • More

Wake up to day 4 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.

Take the opportunity to see Main Square. This attraction has an average rating of 4.6 out of 5 stars from 152,388 visitors.

Market Of San Miguel is another sightseeing hotspot in the area. This building has been rated an average of 4.4 out of 5 stars by 106,296 travelers.

Madrid is also the home of Círculo De Bellas Artes. Around 27,540 people have rated this movie theater an average of 4.4 out of 5 stars.

Another place you’ll want to visit is Thyssen-bornemisza Museum, which hosts up to 671,078 visitors every year. With an average rating of 4.6 out of 5 stars from a total of 32,846 reviews, a visit to this art museum is a great idea.

This day of your vacation in Madrid is also your chance to admire Museo Del Prado. This must-visit art museum enjoys an average rating of 4.7 out of 5 stars from 98,929 reviews. Approximately 3,497,345 people travel to Madrid every year to see this attraction with their own eyes.

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.

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.

Dive into a culinary adventure like no other in Toledo by booking a table at Iván Cerdeño. This popular restaurant holds 2 Michelin star and offers an exceptional menu of modern cuisine. If you're in the mood to try something new, consider Tobiko Restaurante, another top spot with a mouthwatering menu.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Buca Bar, a well-loved spot among locals and tourists. Or, head to Pub "o'briens". This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Terraza Miradero, another top-rated place in the area.

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 5

Day 5 – Toledo

  • Toledo
  • More

Drive 6 km, 31 min

  • Iglesia de Santo Tomé
  • Monasterio de San Juan de los Reyes
  • FLY TOLEDO
  • San Martin's Bridge
  • Mirador del Valle
  • More

Day 5 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.

An excellent attraction to start your day with is Iglesia De Santo Tomé. This church is rated an average of 4.4 out of 5 stars in 5,277 reviews.

Continue your journey at Monasterio De San Juan De Los Reyes, Toledo. This monastery is rated 4.6 out of 5 stars by 6,783 travelers from near and far.

Toledo is also the home of Fly Toledo. This point of interest has an average rating of 4.8 out of 5 stars from 2,381 visitors.

You can continue your self-guided sightseeing tour at San Martin's Bridge. Rated 4.7 out of 5 stars by 10,516 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Mirador Del Valle. With an average rating of 4.8 out of 5 stars from 10,058 reviews, it’s hard to refuse the opportunity to see this landmark.

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 Toledo for you so you can browse their menus in advance and make a reservation.

Make sure to reserve a table at Restaurante Taberna El Gallo Toledo, an iconic dining spot in Toledo. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Clandestina, a popular restaurant in Toledo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Restaurante "El Cobertizo", a hidden gem nestled in Toledo. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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Day 6

Day 6 – Toledo, and Avila

  • Ávila
  • Toledo
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Drive 134 km, 2 hours 20 min

  • Santa Iglesia Catedral Primada de Toledo
  • Alcázar de Toledo
  • Zocodover
  • Alcantara Bridge
  • Puerta de Bisagra
  • More

On day 6 of your luxury holiday in Spain, your road trip route will take you exploring the best of Toledo. The day's journey will conclude in Avila, 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.

Make Santa Iglesia Catedral Primada De Toledo your first stop of the day. Previous visitors have rated this church an average of 4.7 out of 5 stars in 27,938 reviews.

Next up, make a stop at Alcázar Of Toledo. With an average rating of 4.6 out of 5 stars by 30,193 visitors, it's easy to understand why so many people visit this alcázar every year.

Zocodover is another attraction you can visit on this day of your vacation. This sightseeing destination has an average rating of 4.5 out of 5 stars by 19,930 visitors.

When you’re finished at Zocodover, the perfect next stop is Alcantara Bridge. This sightseeing destination is rated an average of 4.7 out of 5 stars in 8,836 reviews.

If you’re keen to explore even more, then consider a visit to Puerta De Bisagra. This city gate is a top place to visit, with a rating of 4.7 out of 5 stars from 9,260 reviews.

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

In Avila, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.

Enjoy an outstanding dining experience at Barro, a 1-star Michelin restaurant offering an exceptional creative menu. Alternatively, experience a taste of Avila at Cervecería La Cigueña, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar La Mezquita, known for its inviting atmosphere. La Oca Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, The Black Rose provides a great setting to enjoy the night away.

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

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Day 7

Day 7 – Avila, Salamanca, and Valladolid

  • Valladolid
  • Ávila
  • Salamanca
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Drive 230 km, 2 hours 53 min

  • Muralla de Ávila
  • Salamanca Cathedral
  • Huerto de Calixto y Melibea
  • Roman bridge of Salamanca
  • More

Wake up to day 7 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 Valladolid, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Avila, and Salamanca.

An excellent attraction to start your day with is Walls Of Ávila. This city walls is rated an average of 4.8 out of 5 stars in 14,534 reviews.

Continue your journey at Cuatro Postes Lookout - Viewpoint Of Ávila. This sightseeing destination is rated 4.7 out of 5 stars by 5,843 travelers from near and far.

After soaking in Avila’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Salamanca. Expect your car journey to take a minimum of 1 hour. When you arrive in Salamanca, it's time to take a break from the road.

An excellent attraction to start your day with is Salamanca Cathedral. This church is rated an average of 4.7 out of 5 stars in 14,562 reviews.

Continue your journey at Calisto And Melibea Vegetable Garden. This park is rated 4.5 out of 5 stars by 11,760 travelers from near and far.

Salamanca is also the home of Roman Bridge Of Salamanca. This bridge has an average rating of 4.7 out of 5 stars from 9,869 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 an extraordinary dining experience at Alquimia - Laboratorio, a 1-star Michelin restaurant offering an incredible creative, and modern menu. Alternatively, if your taste buds call for something different, Trigo is one of the best restaurants for modern cuisine in Valladolid. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Llantén. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for traditional cuisine in the city.

Following your dinner, dive into the local bar culture at The Lost Child Cocktail's Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Café Bar Alborada, the perfect place for those looking to experience the best of the nightlife. Similarly, Monasterio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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 8

Day 8 – 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 8 of your luxury holiday in Spain! Remember to have a hearty breakfast because today will be filled with memorable adventures in Segovia, and Real Sitio de San Ildefonso. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

As you’ve unraveled the marvels of Valladolid, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Segovia may take around 1 hour 21 min. Upon your arrival in Segovia, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Begin your sightseeing with a visit to Alcázar Of Segovia. This alcázar gets 754,946 visitors each year and is rated an average of 4.7 out of 5 stars in 49,713 reviews.

Next up, make your way to Segovia Cathedral. This catholic cathedral has an average rating of 4.7 out of 5 stars from 18,509 reviews.

When you’re ready for your next sight of the day, continue to Aqueduct Of Segovia. This stone bridge has an average rating of 4.8 out of 5 stars from 95,202 visitors.

When you’re ready to jump back into the car and say goodbye to Segovia, you’ll hit the road in the direction of Real Sitio de San Ildefonso. This drive usually takes around 17 min. When you arrive, enjoy some sightseeing.

Make Royal Palace Of La Granja Of San Ildefonso one of your first sightseeing stops in Real Sitio de San Ildefonso. Rated an average of 4.6 out of 5 stars by 19,635 travelers, a visit to this local attraction makes for a great introduction to the area.

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.

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

Enjoy a delicious meal at Sagaretxe, a highly-rated dining destination in Madrid. If you're eager to try something different, consider Arrabal Madrid, another top spot with a tantalizing menu. You might also want to secure a reservation at Taberna El Sur. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Madrid this evening.

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

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Day 9

Day 9 – Madrid - departure day

  • Madrid - Departure day
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  • Western Park
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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 Madrid before saying goodbye.

Make the most of your final day in Spain by visiting Madrid’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 Western Park. This extraordinary park and attraction is rated an average of 4.5 out of 5 stars in 28,992 reviews, and is an excellent choice for your last sightseeing in Madrid.

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

You will then say farewell to Madrid 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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