Luxury 10-Day Spain Road Trip from Madrid to Toledo and Cuenca and surrounding area

Your luxury holiday in Spain begins as soon as you reach the city of Madrid, where you'll be staying for 6 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

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, we recommend you try one of the best places to eat in Madrid. Enjoy the local flavors, unwind, and reflect on the day's adventures.

Reserve a table at DiverXO, a 3 Michelin star restaurant and a Bib Gourmand dining establishment in Madrid. This epicurean hotspot’s delicious creative offering makes it a crowd favorite. DiverXO is highly regarded in the culinary world and boasts an impressive track record of satisfied customers.

Another popular dining spot in Madrid is Smoked Room, which critics have graced with 2 Michelin stars. This Bib Gourmand establishment’s pleasant ambiance and food choices leave a lasting impression on everyone who dines here. Its contemporary menu, characterized by its exquisite flavors, is a true testament to the Smoked Room’s culinary excellence.

Locals and foreign travelers alike recommend the popular Bib Gourmand restaurant, Paco Roncero. Captivated customers consistently praise this restaurant in Madrid for its appetizing selection of food, including its creative courses. As a leading food haven, it boasts 2 Michelin stars for giving an unforgettable dining experience to its patrons.

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Madrid.

Many locals go to El miniBAR for an evening cocktail or glass of wine. This bar is rated an average of 4.7 out of 5 stars by 4,297 customers.

If you feel like going somewhere else, another popular option in the city is Areia. This bar has an average rating of 4.4 out of 5 stars by 3,973 customers.

Raise a toast to the start of your 10-day luxury vacation in Spain and look forward to more fantastic days to come!

On day 2 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Madrid. You’ll stay in Madrid for 5 nights, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Madrid to the fullest.

This activity is one of many you can add to your luxury travel plan to make your vacation in Spain truly memorable.

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

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

Celebrate this wonderful day with sumptuous cocktails at 1862 Dry Bar, a terrific bar to unwind after a busy day. Around 1,987 customers rated this bar with an impressive average of 4.6 out of 5 stars.

You can continue your amazing night of celebration at Taberna del Alabardero de Madrid. This bar has been rated an average of 4.3 out of 5 stars by 1,525 customers, and is an excellent place to mingle with locals and fellow travelers.

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.

On day 3 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Madrid. You’ll stay in Madrid for 4 nights, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Madrid to the fullest.

This activity is one of many you can add to your luxury travel plan to make your vacation in Spain truly memorable.

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 Madrid. Savor the local cuisine and relax as you recount the day's experiences.

As your day in Madrid is coming to an end, retreat to a bar where you can celebrate the start of your exciting luxury holiday in Spain. Enjoy a signature cocktail or a glass of fine wine as you toast to the adventures that await you.

If you’re up for classic drinks with a modern flair, consider going to Baton Rouge Cocktail Bar. Around 966 customers have given this incredible bar an average rating of 4.6 out of 5 stars.

Locals of Madrid also enjoy the cocktails at Harvey's Cocktail Bar. This place is rated an average of 4.4 out of 5 stars by 1,137 customers and is one of the best you can experience in the city.

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.

Day 4 of your luxury itinerary in Madrid will be filled with memorable experiences. With magnificent attractions, delicious food, and great entertainment, you're guaranteed a lovely day in the city. Make the most out of the 3 nights you have left of your luxury holiday in Madrid.

This activity is one of many you can add to your luxury travel plan to make your vacation in Spain truly memorable.

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.

As your first day in Madrid is coming to an end, retreat to a bar for some celebration. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

Whether you prefer your drink shaken or stirred, Cafe Madrid is a great place to enjoy a well-deserved celebratory drink. This bar is rated an average of 4.4 out of 5 stars from 662 customers.

Alternatively, check out Inclán Brutal Bar, a place many travelers consider their favorite in Madrid. Inclán Brutal Bar offers drinks for every taste and is rated an average of 4.4 out of 5 stars by 662 guests.

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

On day 5 of your exciting luxury holiday across Spain, you will continue exploring the city of Segovia. You still have 2 nights left in the city. Enjoy your break from the road and spend this day sightseeing and eating at some of the best restaurants in Segovia. Your accommodation will be conveniently located close to several of the best attractions in the city.

This activity is one of many you can add to your luxury travel plan to make your vacation in Spain truly memorable.

After a long day of exploring top attractions in the area, 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 the city for you, so you can check out the menus and make your reservation in advance.

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Madrid.

Many locals go to Taberna El Sur for an evening cocktail or glass of wine. This bar is rated an average of 4.5 out of 5 stars by 5,959 customers.

If you feel like going somewhere else, another popular option in the city is Mercado de la Reina 12. This bar has an average rating of 4.2 out of 5 stars by 6,470 customers.

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.

On day 6 of your luxurious vacation in Spain, you’ll start and end your day in Madrid, but spend most of the day exploring attractions outside of the city. On this day of your road trip you’ll get the chance to visit exciting attractions in the city of Real Sitio de San Ildefonso and the village of Valsaín. After a long day of sightseeing, you'll drive back to Madrid, where you'll stay for 1 night more.

Valsaín’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Madrid behind. This drive usually takes around 1 hour 10 min. Valsaín welcomes you with a multitude of unique vacation experiences.

Journey into the unknown at Área recreativa Los Asientos, a unique attraction awaiting your visit. This remarkable park has an average rating of 4.5 out of 5 stars from 1,454 reviews.

Real Sitio de San Ildefonso’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Valsaín behind. This drive usually takes around 7 min. Real Sitio de San Ildefonso welcomes you with a multitude of unique vacation experiences.

When you arrive, enjoy some sightseeing.

When you’re done exploring the best attractions, you’ll drive back to your luxury accommodation near the city of Madrid.

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.

Check out La Bien Aparecida. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.5 out of 5 stars from 2,473 reviews.

Locals also recommend Prada a Tope Madrid as one of the best restaurants to have dinner at in Madrid. Prada a Tope Madrid is rated an average of 4.4 out of 5 stars by 2,511 customers, including locals as well as travelers.

As the day is coming to an end, you can head back to your hotel to relax, or, go out for a drink.

Whether you prefer your drink shaken or stirred, Café Central is a great place to enjoy a well-deserved celebratory drink. This bar is rated an average of 4.1 out of 5 stars from 5,181 customers.

Alternatively, check out Mas Al Sur, a place many travelers consider their favorite in Madrid. Mas Al Sur offers drinks for every taste and is rated an average of 4.1 out of 5 stars by 5,181 guests.

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.

Wake up to day 7 of your luxury holiday in Spain! Remember to have a hearty breakfast because today will be filled with memorable adventures in Hinojosa de San Vicente, Talavera de la Reina, Santo Domingo-Caudilla, and Toledo. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries. Your stay of 1 night at a luxury hotel in Toledo adds a touch of comfort to your journey.

Embrace the thrill of the open road as you wave goodbye to Madrid and set your GPS to Hinojosa de San Vicente. 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 24 min. Upon reaching Hinojosa de San Vicente, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Fasten your seatbelt and make your way to your next stop. Talavera de la Reina, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Hinojosa de San Vicente to Talavera de la Reina may take around 20 min without traffic disruptions. Upon arrival, we highly recommend checking out some of the top attractions.

When you arrive, enjoy some sightseeing.

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

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.

Check out Bar La Malquerida de la Trinidad. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.4 out of 5 stars from 5,059 reviews.

Locals also recommend Restaurante Alfileritos 24 as one of the best restaurants to have dinner at in Toledo. Restaurante Alfileritos 24 is rated an average of 4.3 out of 5 stars by 3,860 customers, including locals as well as travelers.

Alternatively, for another culinary experience you will remember, book a table at Restaurante Hierbabuena. This popular restaurant has an average rating of 4.5 out of 5 stars by 1,791 customers.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

One of the top bars in Toledo is La Clandestina. This claim is supported by 1,595 customers who have rated it an average of 4.5 out of 5 stars.

Another great bar with an extensive drink menu is La Cave. If you ask the 1,714 customers who have rated it an average of 4.3 out of 5 stars, La Cave is the perfect place for a unique drinking experience.

Locals also enjoy El Trébol, a great place to experience the local scene and unwind during your visit. This bar has an average rating of 4.3 out of 5 stars by 7,790 customers.

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

Wake up to day 8 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 Cuenca, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Consuegra, Ocaña, and Cuenca.

Consuegra’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Toledo behind. This drive usually takes around 50 min. Consuegra welcomes you with a multitude of unique vacation experiences.

After soaking in Consuegra’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Ocaña. Expect your car journey to take a minimum of 49 min. When you arrive in Ocaña, it's time to take a break from the road.

Continue your road trip and head to your next destination, Cuenca. This car ride takes around 1 hour 16 min.

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

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

According to reviews, Grotte del Huécar is one of the absolute best places to eat in Cuenca. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.4 out of 5 stars from 2,935 reviews.

Alternatively, if you’re curious to try a local favorite, check out Restaurante Recreo Peral. This restaurant is rated an average of 4.4 out of 5 stars by 2,722 customers and guarantees you a nice dining experience to end your day.

If your taste buds call for something different, book a table at Restaurante El Torreón. This popular restaurant has an average rating of 4.4 out of 5 stars by 1,390 customers.

After dinner, visit some of the best bars in the city of Cuenca. Strike up a conversation with the friendly locals to end the day perfectly.

When you’ve finished your meal, visit Las Brasas for a well-deserved after-dinner drink. One of the best bars in the city, Las Brasas has an average rating of 4.4 out of 5 stars from 1,335 customers.

If you’d rather go to a different spot, La Ronería De La Habana is another great option. This bar enjoys an average rating of 4.3 out of 5 stars from 1,072 bar-goers.

Restaurante Sidrería La Figal is also a great city bar with a welcoming atmosphere. Restaurante Sidrería La Figal has an average rating of 4.3 out of 5 stars from 1,526 customers.

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

On day 9 of your luxury holiday in Spain, your road trip route will take you exploring the best of Cuenca, Cuenca, and Madrid. The day's journey will conclude in Madrid, 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.

Soak in the beautiful landscapes as you drive and look forward to exploring your next destination.

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

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

At the top-rated restaurant Arrabal Madrid, you can enjoy a mouthwatering selection of both food and drinks. This restaurant has an average rating of 4.5 out of 5 stars by 1,924 customers.

As the day is coming to an end, you can head back to your hotel to relax, or, go out for a drink.

Cap off the evening at Cervantes Cervecería. This bar has an average rating of 4.3 out of 5 stars from 3,073 customers and is one of the best bars in Madrid.

Another popular place to go for refreshing drinks and delicious bites is Sagaretxe. Rated an average of 4.1 out of 5 stars by 3,358 customers, this spot offers customers an unforgettable bar experience.

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.

Today is the last day of your 10-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.

On your last day in Spain, take time to indulge in shopping at Madrid’s popular marketplace. Thanks to your accommodation’s strategic location, city’s bustling commercial district is only a stone’s throw away, giving you ample time to leisurely explore the area, filled with local shops.

Take time to find the perfect present, reminding you of the charms of Spain. Each store here is brimming with unique finds.

Don’t travel hungry. Take the opportunity to savor the local cuisine in 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!