Luxury One-Week Spain Road Trip from Madrid to 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 5 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

When you’re ready for some sightseeing, make your way to plaza de España. This much-appreciated square is rated 4.4 out of 5 stars in 98,199 reviews.

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 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 Madrid so you can check out the menus and make advance reservations.

After savoring a delicious meal, step into the vibrant nightlife at Baton Rouge Cocktail Bar, where the evening is just getting started. In the same way, Cafe Madrid offers a unique charm perfect for experiencing the local bar scene in Madrid. 1862 Dry Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise a toast to the start of your 8-day luxury vacation in Spain and look forward to more fantastic days to come!

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 4 nights nights remaining.

Kick off the day at Santiago Bernabéu Stadium, a top pick for today’s sightseeing. This association football venue is rated an average of 4.6 out of 5 stars in 120,158 reviews.

Today is also your chance to visit Crystal Palace. Crystal Palace is a building with an average rating of 4.6 out of 5 stars from 39,270 reviews.

El Retiro Park is another top attraction we highly recommend you visit today. This urban park is rated an average of 4.8 out of 5 stars by 162,386 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Museo del Prado. This art museum is rated an average of 4.7 out of 5 stars by 98,929 visitors. Visiting Museo del Prado means you'll be one of 3,497,345 people who do so every year.

Lastly, don’t miss out on Casa de Campo, a famous park in Madrid. This attraction is rated an average of 4.5 out of 5 stars by 50,826 travelers.

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

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

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 3 nights nights remaining.

A top pick for your self-guided sightseeing tour today is Museo Nacional Centro de Arte Reina Sofía. Over 1 traveler visit this attraction every year. Previous visitors have rated this art museum an average of 4.5 out of 5 stars in 46,855 reviews.

Main Square is a local recommendation that you also can pay a visit today. This square is rated an average of 4.6 out of 5 stars in 152,388 reviews.

Another attraction you won't want to miss is Market of San Miguel. This building is rated an average of 4.4 out of 5 stars in 106,296 reviews.

Royal Palace of Madrid is another outstanding experience in Madrid. Around 77,471 travelers have rated this royal palace an average of 4.6 out of 5 stars.

If you long for more, Temple of Debod is not far away. This egyptian temple is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.4 out of 5 stars in 44,446 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.

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 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.

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 Madrid so you can check out the menus and make advance reservations.

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.

Day 5 of your luxury road trip in Spain is another opportunity to explore what this region has to offer. Start your day with a drive to visit the amazing attractions in the surrounding area of Madrid. After a day of sightseeing, return to the city, where you still have 1 night nights left to enjoy. End your evening with a fulfilling dinner at one of the finest restaurants in Madrid, savoring the local culinary delights.

Segovia’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Real Sitio de San Ildefonso behind. This drive usually takes around 20 min. Segovia welcomes you with a multitude of unique vacation experiences.

Start your sightseeing with a visit to Mirador de la Pradera de San Marcos. This sightseeing destination is rated an average of 4.8 out of 5 stars from 2,894 visitors.

Alcázar of Segovia is another popular attraction you could visit today. This alcázar has a rating of 4.7 out of 5 stars from 49,713 visitors. Alcázar of Segovia attracts up to 754,946 visitors every year.

Fasten your seatbelt and make your way to your next stop. Real Sitio de San Ildefonso, 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 Madrid to Real Sitio de San Ildefonso may take around 1 hour 13 min without traffic disruptions. Upon arrival in Real Sitio de San Ildefonso, we highly recommend checking out some of the top attractions.

Kick off the day at Royal Palace of La Granja of San Ildefonso, a top pick for today’s sightseeing. This museum is rated an average of 4.6 out of 5 stars in 19,635 reviews.

When you’ve had your share of Madrid, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Real Sitio de San Ildefonso. Your travel time is around 1 hour 13 min.

Seize the day by visiting some of the best attractions in the area, like Royal Palace of Riofrío. This extraordinary royal palace has an average rating of 4.5 out of 5 stars from 3,059 visitors.

When you’ve completed everything you want to see and do, you will drive back to your luxury accommodation in Madrid.

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

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.

Wake up to day 6 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 Azuqueca de Henares, Guadalajara, and Torija.

As you’ve unraveled the marvels of Madrid, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Azuqueca de Henares may take around 45 min. Upon your arrival in Azuqueca de Henares, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make Quebradilla Park your first stop of the day. Previous visitors have rated this park an average of 4.2 out of 5 stars in 1,847 reviews.

Guadalajara’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Torija behind. This drive usually takes around 17 min. Guadalajara welcomes you with a multitude of unique vacation experiences.

Your sightseeing of the day begins at Santa Maria, a remarkable church where it’s easy to get lost in exploration. This top attraction is rated an average of 4.3 out of 5 stars in 1,112 reviews.

Next, satisfy your wanderlust at San Roque Park. This park has an average rating of 4.4 out of 5 stars from 1,342 travelers.

Set your GPS to Torija and hit the road. Expect a journey of approximately 24 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Torija beckons with new experiences!

A top pick for your self-guided sightseeing tour today is Castle of Torija. Previous visitors have rated this castle an average of 4.4 out of 5 stars in 3,875 reviews.

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.

After your meal, keep the night alive at a bar like Café Hispano, known for its lively atmosphere. Bogart is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, CAFE BAR PRINCESA offers an excellent atmosphere for those looking to amp up the evening.

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.

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 Cuenca. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Admire the views and listen to some good music as you drive in the direction of Cuenca.

Seize the day by visiting some of the best attractions in the area, like Castilla-La Mancha Paleontological Museum. This extraordinary fossil museum has an average rating of 4.7 out of 5 stars from 5,372 visitors.

Next, make your way to San Pablo Bridge. This bridge is rated an average of 4.6 out of 5 stars in 2,784 reviews.

While in Cuenca, we also recommend a visit to Castillo de Cuenca. This museum has been rated an average of 4.5 out of 5 stars in 2,266 reviews.

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

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.

With its reputation for pleasing customers, it’s a fantastic choice for tonight in Madrid.

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

Today is the last day of your 8-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, the 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. These souvenirs will help you treasure your memories of Spain forever.

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

Savor the flavors at Taberna del Alabardero de Madrid, a top pick for dinner tonight. Alternatively, Café Central beckons with its unique menu offerings.

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!