Luxury 5-Day Spain Self-Drive Road Trip With Itinerary from Madrid traveling east to Cuenca

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Description

Escape for the holiday of a lifetime with this 5-day luxury road trip 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 Madrid and 1 night in Cuenca, 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 5-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 5-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 5-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 and Cuenca 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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Itinerary summary

See a summary of the itinerary that you can fully customize

Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Puerta de Alcalá
Santiago Bernabéu StadiumMuseo del PradoMuseo Nacional Centro de Arte Reina SofíaTemple of DebodCasa de CampoEl Retiro Park
Main SquareMarket of San MiguelRoyal Palace of MadridEl Retiro ParkCrystal Palace
Castilla-La Mancha Paleontological MuseumTorre de ManganaScience Museum of Castilla La ManchaSan Pablo Bridge
plaza de EspañaEl Retiro Park

Personalize your itinerary

Customize tours under each day and destination

Day 1

Day 1 – Madrid - arrival day

  • Madrid - Arrival day
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  • Puerta de Alcalá
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Your luxury holiday in Spain begins as soon as you reach the city of Madrid. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Madrid is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Puerta De Alcalá or taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

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.

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

Dine in style at Restaurante Taberna Madrid Madriz, a top recommendation for dinner tonight. Or, for a change of pace, Lamucca del Carmen boasts a menu that's sure to impress. Also, be sure to check out El miniBAR. Known as a local hotspot, it’s a great choice for tonight in Madrid.

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

Raise a toast to the start of your 5-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 28 km, 3 hours 24 min

  • Santiago Bernabéu Stadium
  • Museo del Prado
  • Museo Nacional Centro de Arte Reina Sofía
  • Temple of Debod
  • Casa de Campo
  • El Retiro Park
  • 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 1 night remaining.

Immerse yourself in Madrid’s rich culture with today's sightseeing itinerary. Start your journey at Santiago Bernabéu Stadium. This historic stadium is sure to ignite your curiosity. Next, dive into the photogenic features of Museo Del Prado, a must-visit museum in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Museo Nacional Centro De Arte Reina Sofía, an astonishing museum. For a change of scene, check out Temple Of Debod, known for its visually striking features.

Spain is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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.

Enjoy an outstanding dining experience at DiverXO, a 3-star Michelin restaurant offering an exceptional creative menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Smoked Room, known for its delicious contemporary cuisine. Another highly-recommended restaurant in Madrid is Paco Roncero, a renowned restaurant with a 2-star Guide Michelin recognition, known for its delicious creative menu.

Explore the vibrant nightlife at Jazz Bar after your meal, a hub for lively evenings and memorable moments. Or, head to España Building for a great selection of flavorful drinks and a charming setting. Furthermore, 1862 Dry Bar is perfect for those looking to extend their night with a touch of local flavor.

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 – Madrid and Cuenca

  • Madrid
  • Cuenca
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Drive 172 km, 2 hours 20 min

  • Main Square
  • Market of San Miguel
  • Royal Palace of Madrid
  • El Retiro Park
  • Crystal Palace
  • More

On day 3 of your luxury holiday in Spain, your road trip route will take you exploring the best of Madrid. The day's journey will conclude in Cuenca, 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.

Discover a day packed with a romantic, a breathtaking, a photogenic, a historic, a culturally significant, and a masterful in Madrid. Begin your sightseeing with Main Square. This world-famous public square is one of the top attractions in the city. Proceed to Market Of San Miguel, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Madrid, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Royal Palace Of Madrid. This timeless palace is a traveler-favorite. Not far away, you’ll find Crystal Palace, another key site on your sightseeing itinerary.

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

Have a memorable dining experience in Cuenca by booking a table at Olea Comedor, renowned as a Bib Gourmand restaurant presenting an exceptional modern and fusion menu. Immerse yourself in the culinary delights of Sibuya Urban Sushi Bar, a popular restaurant in Cuenca. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

Continue your lively evening at Bar Tu Rincón, a perfect place for winding down or revving up the night, depending on which mood you’re in. Café Hispano is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bogart ensures a night out tailored to your taste.

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 4

Day 4 – Cuenca and Madrid

  • Cuenca
  • Madrid
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Drive 170 km, 2 hours 38 min

  • Castilla-La Mancha Paleontological Museum
  • Torre de Mangana
  • Science Museum of Castilla La Mancha
  • San Pablo Bridge
  • 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 Cuenca. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Today’s route brings a visually striking, a historic, a breathtaking, a culturally significant, a charming, and an UNESCO world heritage-listed. The first attraction of today is Castilla-la Mancha Paleontological Museum. This increasingly popular museum is a history-steeped place to see in Cuenca. Continue your discovery at Torre De Mangana, a picture-perfect monument with stories to tell.

As you stroll around Cuenca, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Science Museum Of Castilla La Mancha. San Pablo Bridge is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Cuenca.

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.

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

Make sure to reserve a table at Areia, 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 La MaMá Restaurante, 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 Sacha Restaurant, 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 a toast to another amazing day of your luxury holiday in Cuenca, Spain and seize the opportunity to celebrate.

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Day 5

Day 5 – Madrid - departure day

  • Madrid - Departure day
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  • plaza de España
  • El Retiro Park
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Today is the last day of your 5-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.

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

Make the most of what's left of your luxury vacation and head out to the stunning Plaza De España. This extraordinary public square and attraction is rated an average of 4.4 out of 5 stars in 98,199 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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