Relaxed 9-Day Spain Self-Drive Road Trip With Itinerary from Madrid to Toledo

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Discover stunning scenery and hidden gems on this 9-day relaxed road trip in Spain! Madrid, Segovia, and Toledo await with vibrant culture and lasting memories as you unwind on this self-drive vacation.

Travel freely with this relaxed self-drive package in Spain, designed for comfort and exploration. Spend 5 nights in Madrid and 3 nights in Toledo, staying at top-rated hotels near the heart of each city. Between drives, indulge in local cuisine, sip refreshing drinks, and enjoy the vibrant atmosphere at popular restaurants and bars along your road trip route in Spain.

Your journey starts in Madrid, where your rental car with CDW insurance will be ready for pickup. Choose a vehicle that suits your style, then set off on your 9-day relaxed road trip in Spain to explore its rich culture, fascinating history, and stunning landscapes.

Every stop on this leisurely self-drive holiday comes with handpicked accommodations that make relaxation effortless. Choose from elegant 5-star hotels with breathtaking views or comfortable 3-star stays that offer excellent value, all providing a welcoming retreat after a day on the road.

With your self-drive itinerary in Spain already planned, you’ll enjoy the country’s most celebrated sights without the rush. Marvel at the stunning El Retiro Park and soak in the atmosphere of the magnificent Main Square.

Enjoy each stop as you explore the history, architecture, and character of each destination on this Spain road trip itinerary for 9 days.

As you travel between destinations, you’ll have plenty of time to explore local markets and boutique shops. These stops give you the chance to find unique souvenirs, taste regional specialties, and experience everyday life in Spain.

If you want to make your 9-day relaxed self-drive tour in Spain even more memorable, add optional tours or activities. Join a guided excursion, discover hidden neighborhoods, or spend an afternoon in your favorite market. Each choice deepens your connection to the places you visit.

Alongside these experiences, your laid-back self-drive package in Spain includes 8 nights in comfortable hotels, a rental car for 9 days, and convenient access to nearby dining options. You can also add flights and entry tickets to shape the trip exactly how you want it. With 24/7 travel support and a mobile app keeping your itinerary and documents organized, you can enjoy a relaxed drive and savor every mile of the road ahead.

Turn your travel plans into reality. Book your 9-day relaxed self-drive road trip in Spain today and enjoy a journey filled with discovery, freedom, and unforgettable moments!

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Driver’s age is 30 - 65
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Pick-up: 10:00
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Day1

Day 1

  • Madrid - Arrival day
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  • plaza de España
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Your relaxed road trip through Spain starts when you reach the incredible city of Madrid, where you'll stay for 4 nights. You'll pick up your rental car in Madrid and begin your adventure in Spain.

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 Plaza De España. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Madrid. Make yourself at home and unwind before heading out again.

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.

Treat yourself to a delicious dinner at Restaurante Taberna Madrid Madriz, an excellent option for tonight's dining. Looking for something different? Lamucca del Carmen offers a tantalizing alternative with its diverse menu. And don’t miss El miniBAR. Known for great service, it’s a fantastic choice for tonight in Madrid.

Before calling it a day, visit one of the best bars in Madrid. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

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

Raise a toast as you look back on the highlights of today’s relaxed road trip in Spain. Enjoy your first taste of Madrid as you soak in the city’s unique vibe.

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Day2

Day 2

  • Madrid
  • More

Drive 9 km, 1 hour 3 min

  • Museo Nacional Centro de Arte Reina Sofía
  • Main Square
  • Market of San Miguel
  • Royal Palace of Madrid
  • Temple of Debod
  • More

Day 2 introduces you to many popular attractions and activities in Madrid, further proving that leisurely self-drive tours in Spain are extraordinary.

Awaiting your discovery is the widely recognized Museo Nacional Centro De Arte Reina Sofía, a heritage-rich museum in Madrid. Next, go to Main Square.

After visiting Museo Nacional Centro De Arte Reina Sofía and Main Square, have a stroll along Madrid's streets and take in the local charm. Continue your sightseeing by heading to Market Of San Miguel. This photogenic food market offers a unique experience. Royal Palace Of Madrid is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Temple Of Debod, one of the most visually striking places to visit in Madrid.

Spain makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Spain also offers plenty of tours to enhance your relaxed road trip experience.

When you’re not driving and exploring some of the best places in Spain, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Madrid.

Experience a taste of local culinary excellence while in Madrid by securing a table at DiverXO. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Smoked Room, famous for its scrumptious contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Paco Roncero, a local favorite celebrated for its exquisite creative cuisine in Madrid. Located in the heart of the city, this 2-star Michelin restaurant is an ideal pick for creative cuisine lovers seeking top-notch culinary experiences.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

Keep the evening going at Jazz Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to España Building, which offers a similarly pleasant setting and great drinks. Another option is 1862 Dry Bar, which provides an inviting environment for unwinding after a busy day out.

Savor the rest of the night and celebrate another incredible, relaxed road trip adventure in the magical Madrid!

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Day3

Day 3

  • Madrid
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Drive 15 km, 1 hour 7 min

  • Santiago Bernabéu Stadium
  • Puerta de Alcalá
  • Great Pond of El Retiro
  • El Retiro Park
  • Crystal Palace
  • More

Day 3 of your relaxed road trip through Spain means 24 hours of making the best memories in Madrid. You’ll go sightseeing at famous attractions in Madrid. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Madrid!

Start your day at Santiago Bernabéu Stadium. This instagrammable stadium is an iconic place to see in Madrid. Then, wander over to Puerta De Alcalá. If enchanting sites excite you, this monument will be right up your alley. Nearby, you’ll also find Great Pond Of El Retiro. This awe-inspiring lake is a favorite among visitors.

Madrid offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, El Retiro Park is a timeless spot in the city that will captivate you with its unique charm. When you’re done at the park, don’t forget to check out the visually striking Crystal Palace. Take a moment to appreciate the fascinating details of this locally renowned art installation.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Spain by joining a traveler-approved tour in Madrid. There are so many fun and eye-opening activities to try out in Madrid that will make your slow-paced self-drive tour in Spain more memorable. Check out all the most recommended and top-rated tour options in the city of Madrid to find the best options for you!

Exploring the food culture in Madrid offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Savor the flavors at Areia, a top pick for dinner tonight. Alternatively, La MaMá Restaurante beckons with its unique menu offerings. Also, consider Sacha Restaurant. With its consistent customer satisfaction, it’s an excellent option for dining in Madrid tonight.

Before calling it a day, visit one of the best bars in Madrid. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Raise your glass and relax after another big day of your leisurely paced road trip in Spain!

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Day4

Day 4

  • Madrid
  • More

Drive 19 km, 1 hour 2 min

  • Casa de Campo
  • Museo del Prado
  • Thyssen-Bornemisza Museum
  • Gran Vía
  • Malasaña
  • More

On day 4 of your leisurely self-drive tour across Spain, you’ll go deep into Madrid, where you'll stay for 1 night, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Madrid, and meet locals along the way!

A visit to Gran Vía is a must on the agenda today. This street is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights. Don’t forget to check out Malasaña as well, a neighborhood that adds another layer to your exploration.

Casa De Campo leaves a lasting impression. This park is one of the most spectacular places to visit in Madrid. Next, head to Museo Del Prado, a globally renowned museum, known for its heritage-rich 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 Thyssen-bornemisza Museum. This historic museum is a highly recommended experience.

Make the most of your time in the country by joining activities that let you discover more about Spain. Check out all of the tours you can join this day of your leisurely self-drive holiday in Spain and ensure the experience of a lifetime.

Exploring new places makes you hungry. Luckily, Madrid has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Treat yourself to a delightful dinner at Taberna Mozárabe, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Restaurante Lakasa? It's another excellent option with a diverse menu. Consider reserving a table at Lambuzo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Madrid.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Madrid.

Soak in the unique atmosphere of Madrid as you commemorate this day of your relaxed road trip with a toast. Cheers to a memorable, leisurely self-drive holiday in Spain!

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Day5

Day 5

  • Madrid
  • Segovia
  • Toledo
  • More

Drive 261 km, 3 hours 23 min

  • Alcázar of Segovia
  • Segovia Cathedral
  • Plaza Mayor
  • Aqueduct of Segovia
  • More

Day 5 of your relaxed road trip across Spain offers a day of exciting discoveries. You’ll start your day in Segovia and drive in the direction of Toledo for some laid-back sightseeing. You’ll end your day in Toledo, where you’ll stay for 3 nights.

Set your GPS to Segovia and hit the road. Expect a journey of approximately 1 hour 16 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Segovia beckons with new experiences!

When you're ready for some sights, head to Alcázar Of Segovia, an impressive castle in Segovia. Explore its awe-inspiring features at your own pace before you continue your journey to your next attraction, Segovia Cathedral. This captivating church is a top recommendation in the area.

When you’re ready to explore more, Plaza Mayor is an excellent choice. Spend some time discovering what some claim to be the most romantic public square in the region. Next, continue your sightseeing at the wondrous Aqueduct Of Segovia and discover what makes this monument unique.

In Toledo, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Spain.

Exploring the food culture in Toledo offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Start your culinary exploration in Toledo by securing a reservation at Iván Cerdeño. This renowned restaurant holds 2 Michelin star and offers an exceptional menu of modern cuisine. Immerse yourself in the culinary delights of La Casa de Damasco, a popular restaurant in Toledo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

Before calling it a day, visit one of the best bars in Toledo. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Continue your lively evening at Buca Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Pub "o'briens" is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Terraza Miradero ensures a night out tailored to your taste.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Spain!

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Day6

Day 6

  • Toledo
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Drive 2 km, 38 min

  • Santa Iglesia Catedral Primada de Toledo
  • Alcázar of Toledo
  • Army Museum
  • Alcantara Bridge
  • More

Day 6 introduces you to many popular attractions and activities in Toledo, further proving that leisurely self-drive tours in Spain are extraordinary.

Whether you decide to explore Toledo 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 well-known Santa Iglesia Catedral Primada De Toledo and allow yourself time to explore. Just a short distance away you'll find your next stop, Alcázar Of Toledo, a breathtaking castle that draws visitors from far and near.

Continue your journey to Army Museum, one of the city’s most curiosity-inducing spots that you shouldn’t miss. Another great site to visit is the up-and-coming Alcantara Bridge.

Another way to make your easygoing and relaxed road trip in Spain more special is by joining unique tours and activities. Toledo offers a wide selection of experiences for every traveler.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Toledo, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Toledo. The bars in Toledo make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Spain!

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Day7

Day 7

  • Toledo
  • More

Drive 7 km, 31 min

  • Mezquita del Cristo de la Luz
  • Puerta del Sol
  • Puerta de Bisagra
  • Paseo de La Vega
  • Mirador del Valle
  • More

Day 7 of your relaxed road trip through Spain means 24 hours of making the best memories in Toledo. You’ll go sightseeing at famous attractions in Toledo. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Toledo!

Experience Mezquita Del Cristo De La Luz, a locally appreciated church in the city. Then, head to Puerta Del Sol and soak in the ambiance of this picture-perfect monument.

There are many interesting places to see in Toledo, and when you are ready for more, go to Puerta De Bisagra. This is one of the city’s most interesting awe-inspiring spots of interest. After exploring the monument, visit the underrated Paseo De La Vega. Not far away, you'll also find Mirador Del Valle. This observation deck is a visually striking highlight in Toledo.

Spain makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Spain also offers plenty of tours to enhance your relaxed road trip experience.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Spain. When you're not appreciating the best places to visit in Toledo, explore the city like a local by trying out the best restaurants in the area.

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 Bar Skala, 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 La Clandestina, a hidden gem nestled in Toledo. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Cherish every minute of your relaxed road trip vacation across Spain.

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Day8

Day 8

  • Toledo
  • Madrid
  • More

Drive 76 km, 1 hour 20 min

  • Iglesia de Santo Tomé
  • Sinagoga de Santa María La Blanca
  • Monasterio de San Juan de los Reyes, Toledo
  • San Martin's Bridge
  • More

Day 8 of your easy, relaxed road trip through Spain lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Toledo. By evening, drive toward the Madrid, where you’ll stay at a top-rated hotel of your choice for 1 night.

Catch Iglesia De Santo Tomé before the crowds roll in. This standout church is sure to ignite your curiosity. Next, dive into the standout features of Sinagoga De Santa María La Blanca, a must-visit synagogue 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 Monasterio De San Juan De Los Reyes, Toledo, a frequently visited monastery. For a change of scene, check out San Martin's Bridge, known for its visually striking features.

Continue your laid-back road trip in Spain as you make your way to Madrid. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Spain. When you're not appreciating the best places to visit in Madrid, explore the city like a local by trying out the best restaurants in the area.

Treat yourself to a delicious dinner at La Mi Venta, an excellent option for tonight's dining. Looking for something different? Mas Al Sur offers a tantalizing alternative with its diverse menu. And don’t miss HanSo Café. Known for great service, it’s a fantastic choice for tonight in Madrid.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Madrid. The bars in Madrid make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Free your mind of worries as you enjoy the taste of freedom on your laid-back road trip adventure across Spain.

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Day9

Day 9

  • Madrid - Departure day
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  • La Latina
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Day 9 of your relaxed road trip in Spain is your departure day. If you’re flying home, return your rental car with time to spare. For a stress-free farewell, book a later flight and enjoy a final, relaxed day in Madrid.

Take some time to indulge in shopping at Madrid’s popular marketplace, Gran Via. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces.

At the top of the list of places to visit today is La Latina, a neighborhood that captures the true essence of Madrid. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Over a good meal, take a moment to unwind and reflect on the past 9 days of your relaxed road trip. Savor one last traditional dish in Madrid, or keep it light with a quick bite before you go.

Treat yourself to a delightful dinner at Prada a Tope Madrid, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Restaurante Morgana? It's another excellent option with a diverse menu.

Give yourself enough time to wave goodbye to Madrid and begin your journey home. The unforgettable experiences you’ve collected along your 9-day relaxed road trip in Spain is a story you will tell for the rest of your life.

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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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