5-Day Spain Self-Drive Road Trip With Itinerary from Madrid to Toledo

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Escape the ordinary with this exciting 5-day road trip through Spain. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Spain. You will spend 3 nights in Madrid and 1 night in Toledo. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Spain. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have you covered.

Upon arriving in Madrid, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Spain on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Spain. El Retiro Park and Main Square are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Museo Del Prado, learn more about the unique Royal Palace Of Madrid, and immerse yourself in the vibrant atmosphere of Aqueduct Of Segovia.

As you hit the open road and drive through Madrid, Toledo, Segovia, and Zamarramala, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Spain. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Spain.

Throughout your road trip in Spain, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Spain.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodations, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Spain fill up quickly, so book your spot early. Select a date and start planning your road trip in Spain today!

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Driver’s age is 30 - 65
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Pick-up: 10:00
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Day 1

Day 1

  • Madrid - Arrival day
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  • Main Square
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Your road trip adventure in Spain begins as soon as you reach Madrid and pick up your car. You’ll stay here for 2 nights and explore what to see in Madrid, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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 Main Square, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Madrid. Check-in typically starts around 2 to 4 PM at hotels in Spain. We recommend staying at a central location for easy access to key areas in the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Madrid, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Restaurante Taberna Madrid Madriz, 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 Lamucca del Carmen, 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 El miniBAR, a hidden gem nestled in Madrid. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Bar Yambala, a prime destination for a thrilling night out. Also, don’t forget to check out Baton Rouge Cocktail Bar, a bar that offers unique local touches. Likewise, Cafe Madrid provides an excellent alternative for a fun evening.

Raise a toast to the start of your 5-day road trip in Spain!

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Day 2

Day 2

  • Madrid
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Drive 11 km, 1 hour 35 min

  • Temple of Debod
  • plaza de España
  • Royal Palace of Madrid
  • El Retiro Park
  • Puerta de Alcalá
  • Museo del Prado
  • More

Day 2 of your road trip across Spain promises a magnificent time exploring what to see in Madrid. You have 1 night left in Madrid. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you decide to explore Madrid on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Look forward to a unique sightseeing adventure at the famous Temple Of Debod and allow yourself time to explore. Just a short distance away you'll find your next stop, Plaza De España, a picture-perfect public square that draws visitors from far and near.

Continue your journey to Royal Palace Of Madrid, one of the city’s most wondrous spots that you shouldn’t miss. Another great site to visit is the globally renowned El Retiro Park. When you're finished at the park, Puerta De Alcalá awaits your visit. This monument is a visually striking highlight on today's itinerary. Last up is a museum - the world-famous Museo Del Prado.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Spain. You can explore and select activities under each day of your itinerary.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Madrid. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Have a fantastic dining experience at Alhambra, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Restaurante Alabaster offers an enticing alternative with its varied menu. Additionally, Restaurante De María - Felíx Boix is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Madrid.

Unwind after your meal by stepping into Jazz Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, España Building offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook 1862 Dry Bar, another top-rated bar in the area.

Raise your glass to another unforgettable day in Spain!

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Day 3

Day 3

  • Madrid
  • Toledo
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Drive 80 km, 1 hour 48 min

  • Mirador del Valle
  • Puerta de Bisagra
  • Monasterio de San Juan de los Reyes, Toledo
  • El Greco Museum
  • Alcázar of Toledo
  • Santa Iglesia Catedral Primada de Toledo
  • More

Your itinerary for day 3 of your road trip in Spain includes 1 stop and features some of the highlights of Toledo. At the end of the day, enjoy the comforts of a top-rated hotel in Toledo, where you'll spend 1 night.

Experience Mirador Del Valle, an interesting observation deck in the city. Then, head to Puerta De Bisagra and soak in the ambiance of this standout monument.

There are many interesting places to see in Madrid, and when you are ready for more, go to Monasterio De San Juan De Los Reyes, Toledo. This is one of the city’s most locally appreciated breathtaking spots of interest. After exploring the monastery, visit the up-and-coming El Greco Museum. Not far away, you'll also find Alcázar Of Toledo. This castle is a stunning highlight in Madrid. Before wrapping up your self-guided sightseeing tour, head to Santa Iglesia Catedral Primada De Toledo, a well-known church in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Toledo. Check in and relax before you head out to tour the city.

Toledo is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Toledo.

Treat yourself to a delicious dinner at Restaurante Museo de Productos de Castilla-La Mancha, an excellent option for tonight's dining. Looking for something different? La Casa de Damasco offers a tantalizing alternative with its diverse menu. And don’t miss La Cave. Known for great service, it’s a fantastic choice for tonight in Toledo.

After enjoying a fulfilling meal, continue your evening at Buca Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Pub "o'briens" offers a welcoming atmosphere for easing into the nightlife. Similarly, Terraza Miradero provides an excellent environment for a relaxed and enjoyable evening.

Take some time to reflect on your day and savor another beautiful night in Spain.

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Day 4

Day 4

  • Toledo
  • Madrid
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Drive 258 km, 3 hours 49 min

  • Aqueduct of Segovia
  • Plaza Mayor
  • Puerta de San Andrés
  • Segovia Cathedral
  • Alcázar of Segovia
  • Mirador de la Pradera de San Marcos
  • More

On day 4 of your exciting self-drive vacation in Spain, you’ll soak in the magnificence of 2 destinations, including Segovia and Zamarramala. When you’re not sightseeing, take time to relax at your chosen hotel in Madrid, where you’ll be staying for 1 night.

Aqueduct Of Segovia leaves a lasting impression. This monument is one of the most iconic places to visit in Toledo. Next, head to Plaza Mayor, an increasingly popular public square, known for its history-steeped features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Puerta De San Andrés. This historic monument is a highly recommended experience. Nearby, you'll also find Segovia Cathedral and Alcázar Of Segovia. Visit these for an interesting touch to your journey. Finish the day with a visit to Mirador De La Pradera De San Marcos, an enchanting observation deck in Toledo.

At the end of the day, you will drive to Madrid, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Indulge in a memorable dining experience at one of Madrid's most popular restaurants, and connect with friendly locals for a true cultural experience.

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

Raise your glass to another unforgettable day in Spain!

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Day 5

Day 5

  • Madrid - Departure day
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  • Gran Vía
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Day 5 of your road trip in Spain is your departure day. This is your chance to catch a last glimpse of Madrid before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

One of the best things to do on your last day is to explore Gran Vía, a street that you shouldn't miss while in Madrid. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Make the most of your final day in Spain by visiting Madrid’s iconic markets and shopping establishments in the buzzing Salamanca District. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing vacation. You can also browse through boutiques for stylish fashion choices. Elevate your style with pieces from high-end retail stores.

Before you conclude your road trip in Spain, drop by another restaurant for a last chance at a memorable dining experience in Madrid.

If you're in the mood to try something new, consider Restaurante Lakasa, another top spot with a mouthwatering menu.

You’ll then say farewell to Madrid. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Spain!

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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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