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

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Photo of aerial  panoramic view of Madrid, Spain.
Photo of the famous Cibeles fountain in Madrid, Spain.
Photo of tourist woman with Spain flag rejoicing against Royal Palace in Madrid.
Photo of crystal Palace (Palacio de cristal) in Retiro Park in Madrid, Spain.
Photo of the Quinta de los Molinos park in Madrid in full spring bloom of the almond and cherry trees.
Photo of royal Palace in Madrid, Spain viewed from the sabatini gardens.
Photo of Madrid city skyline gran via street twilight , Spain.
Photo of Alcala Door (Puerta de Alcala). It was the entrance of the people coming from France, Aragon, and Catalunia. Landmark of Madrid, Spain.
Photo of tourist at the Estanque Grande de El Retiro in the city of Madrid, Spain.
Photo of Madrid, Spain financial district skyline at twilight.
Photo of old street in Madrid, Spain.
Photo of Madrid, Spain. Santa Maria la Real de La Almudena Cathedral and the Royal Palace.
Puerta de Alcalá,Madrid
Santiago Bernabéu Stadium,Madrid
photo of view of Toledo, Spain. Dramatic aerial view of the medieval Toledo Cathedral and Alcazar fortress, twilight colored sky, Castilla La Mancha.
Panoramic view of Alcazar and Alcantara Bridge in the city Toledo, Spain
photo of view of Toledo, Spain - historic Plaza de Zocodover.
photo of view of View of the city Wall in Toledo, Spain.
photo of view of  Historic street with archway in the Old Town of Toledo, Spain
photo of view of Woman tourist enjoying panoramic view of Toledo city- Castilla la Mancha, Spain
photo of view of View from the Tagus river towards the historical center of Toledo, Spain.
photo of view of Touristic view of the streets and details in downtown Toledo, Spain.
photo off view of Bridge San Martin in Toledo, Spain in a beautiful summer night
photo of view of Cityscape of Toledo with the Alcantara bridge in the forefront, Toledo, Spain
photo  of view of Primate Cathedral of Saint Mary of Toledo aerial view at sunset in Spain
photo of view of View of Toledo, Castila la Mancha, Spain, world heritage city with the Alcazar high above on a bright day
photo of view of Aerial view of the medieval old town ( Unesco World Heritage Sites) in the town Toledo, Spain
photo of view of Panoramic view of Alcazar and Alcantara Bridge in the city Toledo, Spain
photo of view of Toledo Skyline with Cathedral, Alcazar and Tagus River at night - Toledo, Spain
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Explore Spain and discover its unique charm on this 9-day relaxed road trip through Madrid, Segovia, and Toledo. Delight in a stress-free journey that focuses on exploration through the country's most captivating landscapes.

This self-drive package allows you to travel through picture-perfect landscapes in Spain at a relaxed pace. Get a dose of comfort, fun, and recreation in Madrid, Segovia, and Toledo. Make yourself at home at top-rated hotels and stay 5 nights in Madrid and 3 nights in Toledo. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Spain.

Freedom of choice is key to a relaxing road trip in Spain. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Madrid, you’ll collect your rental car of choice. From there, you’ll begin your 9-day journey across Spain and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Spain with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Spain.

We’ll introduce you to some of the best travel destinations in Spain. This relaxed road trip features the stunning El Retiro Park. Another highlight of this self-drive tour is the captivating Main Square.

Traveling leisurely through Spain means you could spend as much time as you want at the magnificent Santiago Bernabéu Stadium. With this travel plan, you could also soak in the atmosphere of the memorable Market Of San Miguel. Get close to the spectacular Museo Del Prado and the wonderful Royal Palace Of Madrid. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Spain's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Spain.

Between sightseeing, you can make the most of your downtime and join a popular tour in Spain. This relaxed road trip also gives you plenty of time to stroll through Spain's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Spain.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Spain. You’ll have a cozy place to stay for 8 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 9 days of your self-drive road trip in Spain. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 9-day vacation in Spain and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Spain today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
plaza de España
Museo Nacional Centro de Arte Reina SofíaMain SquareMarket of San MiguelRoyal Palace of MadridTemple of Debod
Santiago Bernabéu StadiumPuerta de AlcaláGreat Pond of El RetiroEl Retiro ParkCrystal Palace
Casa de CampoMuseo del PradoThyssen-Bornemisza MuseumGran VíaMalasaña
Alcázar of SegoviaSegovia CathedralPlaza MayorAqueduct of Segovia
Santa Iglesia Catedral Primada de ToledoAlcázar of ToledoArmy MuseumAlcantara Bridge

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Day 1

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

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Madrid. Make yourself at home and enjoy some downtime 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.

Enjoy a delicious meal at Restaurante Taberna Madrid Madriz, a top-rated dining destination in Madrid. If you're in the mood to try something new, consider Lamucca del Carmen, another top spot with a mouthwatering menu. You might also want to secure a reservation at El miniBAR. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Madrid this evening.

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.

Extend your evening after a delightful meal by visiting Bar Yambala, which offers the perfect atmosphere for a night out. Moreover, Baton Rouge Cocktail Bar is another popular option for a drink or two. Likewise, Cafe Madrid also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 2

Day 2

  • Madrid
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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.

Start by visiting Museo Nacional Centro De Arte Reina Sofía, a prime spot to begin your journey. This instagrammable museum is sure to impress. Next on your list is Main Square, another must-visit landmark and iconic public square renowned for its majestic features.

While exploring and sightseeing, take time to savor the culture of Madrid by sampling some local delicacies. When you’re ready for more sightseeing, head to Market Of San Miguel. This standout food market is an essential place to visit for anyone looking for the full Madrid experience. We also recommend visiting Royal Palace Of Madrid, a wondrous palace. Nearby, you'll also find Temple Of Debod, ready to add charm to your journey.

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

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.

Have a memorable dining experience in Madrid by booking a table at DiverXO, renowned as a 3-star Michelin restaurant presenting an exceptional creative menu. For a different culinary experience in Madrid, Smoked Room shines as one of the top destinations, known for its delicious contemporary cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Paco Roncero is known as a top local spot for its delicious creative cuisine in Madrid. This 2-star Michelin awardee is a highly recommended choice for an unforgettable meal.

If you feel like it, head out to a bar to celebrate another fantastic day in Madrid and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

After your meal, keep the night alive at a bar like Jazz Bar, known for its lively atmosphere. España Building is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, 1862 Dry Bar offers an excellent atmosphere for those looking to amp up the evening.

Look back at an amazing day filled with adventure in Spain. And don’t forget to get some rest so you can continue your relaxed holiday in Spain tomorrow with new energy.

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Day 3

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

On day 3 of your leisurely self-drive tour across Spain, you’ll go deep into Madrid, where you'll stay for 2 nights, 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!

Today’s agenda in Madrid includes a stadium, a monument, a lake, a park, an art installation and much more! Santiago Bernabéu Stadium is must-visit stadium and a great starting point for the day. Next, continue your journey to Puerta De Alcalá, a widely recognized monument, located just a leisurely stroll away. Next, head to Great Pond Of El Retiro, a romantic lake, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Madrid. When you're ready, let your sightseeing route take you to the world-famous El Retiro Park. If you’re looking for more, Crystal Palace is also a popular attraction that is worthwhile a visit.

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!

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.

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.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Spain.

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

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Day 4

Day 4

  • Madrid
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Drive 19 km, 1 hour 2 min

  • Casa de Campo
  • Museo del Prado
  • Thyssen-Bornemisza Museum
  • Gran Vía
  • Malasaña
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Day 4 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!

Gran Vía is one of the highlights of today. Take your time exploring this iconic street in Madrid, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city. Be sure to also visit Malasaña, a neighborhood that showcases another side of Madrid.

Brace yourself for today’s incredible lineup of attractions in Madrid, featuring fun adventures, natural wonders, and scenic views. Start at Casa De Campo, an extraordinary park in the city. Then, head to Museo Del Prado and soak in the ambiance of this respected museum.

There are many interesting places to see in Madrid, and when you are ready for more, go to Thyssen-bornemisza Museum. This is one of the city’s most locally renowned visually striking spots of interest.

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.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

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

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.

A leisurely self-drive holiday in Madrid can’t get any better than this! Toast to another amazing day in Spain!

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Day 5

Day 5

  • Madrid
  • Toledo
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Drive 261 km, 3 hours 23 min

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

Day 5 of your self-drive tour in Spain is your opportunity to see and experience the diversity of the country. You’ll stay in Toledo for 3 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Spain.

Brace yourself for today’s incredible lineup of attractions in Madrid, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Alcázar Of Segovia, an impressive castle in the city. Then, head to Segovia Cathedral and soak in the ambiance of this picture-perfect church.

There are many interesting places to see in Madrid, and when you are ready for more, go to Plaza Mayor. This is one of the city’s most beloved enchanting spots of interest. After exploring the public square, visit the timeless Aqueduct Of Segovia.

When you’re not exploring beautiful places, you’ll have a relaxed time at Toledo. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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.

Get ready for an unforgettable culinary journey in Toledo by reserving a table at Iván Cerdeño. Renowned as a 2-star Michelin restaurant, it offers an exceptional modern menu. If you're in the mood to try something new, consider La Casa de Damasco, another top spot with a mouthwatering menu.

Experience the amazing nightlife in Toledo and unwind at the coolest bars in the city.

Unwind after your meal by stepping into Buca Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Pub "o'briens" offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Terraza Miradero, another top-rated bar in the area.

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

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Day 6

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

Get ready to discover some of the most iconic wonders in Toledo, including a church, a castle, a military museum, a monument and much more! Start your day at Santa Iglesia Catedral Primada De Toledo. This stunning church is a notable place to see in Toledo. Then, wander over to Alcázar Of Toledo. If historic sites excite you, this castle will be right up your alley. Nearby, you’ll also find Army Museum. This instagrammable military museum is a favorite among visitors.

Toledo offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Alcantara Bridge is an underrated spot in the city that will captivate you with its unique charm.

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

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.

Have a fantastic dining experience at Tobiko Restaurante, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Entre Dos Fuegos Restaurante offers an enticing alternative with its varied menu. Additionally, El Trébol is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Toledo.

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.

Toast to another unforgettable and relaxing road trip adventure in Spain!

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Day 7

Day 7

  • Toledo
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Drive 7 km, 31 min

  • Mezquita del Cristo de la Luz
  • Puerta del Sol
  • Puerta de Bisagra
  • Paseo de La Vega
  • Mirador del Valle
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On day 7 of your leisurely self-drive tour across Spain, you’ll go deep into Toledo, 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 Toledo, and meet locals along the way!

Set out on a day brimming with fun adventures, breathtaking views, and photo-friendly spots. Next, go to Puerta Del Sol.

After visiting Mezquita Del Cristo De La Luz and Puerta Del Sol, have a stroll along Toledo's streets and take in the local charm. Continue your sightseeing by heading to Puerta De Bisagra. This respected monument offers a unique experience. Paseo De La Vega is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Mirador Del Valle, one of the most enchanting places to visit in Toledo.

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 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 Toledo.

Treat yourself to a delicious dinner at Restaurante Taberna El Gallo Toledo, an excellent option for tonight's dining. Looking for something different? Bar Skala offers a tantalizing alternative with its diverse menu. And don’t miss La Clandestina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Toledo.

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.

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

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Day 8

Day 8

  • Toledo
  • Madrid
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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
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Day 8 of your leisurely self-drive tour in Spain is another opportunity for an in-depth travel experience in the country. You’ll stay in Madrid for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, picturesque spots, and history-rich sites. 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. Iglesia De Santo Tomé is the first of them. Spend some time admiring this heritage-rich church before continuing your journey. Sinagoga De Santa María La Blanca is your next stop. This beloved synagogue is one of the best-rated sights in Toledo.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Monasterio De San Juan De Los Reyes, Toledo. This picture-perfect monastery is a sight to behold. To round off your sightseeing experience, visit San Martin's Bridge.

Continue your laid-back road trip exploration of the best attractions in Spain at Madrid. Select from top hotels and accommodations in the city to recharge and rejuvenate.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Treat yourself to a wonderful meal at La Mi Venta, a top-rated dining spot in Madrid. If you're in the mood for something new, try Mas Al Sur, another premier location with a delectable menu. You might also want to book a table at HanSo Café. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

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

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Day 9

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 have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Madrid.

On your last day in Spain, take time to indulge in shopping at Madrid’s popular marketplace, Salamanca District. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces. If you’re in the mood for luxury shopping, high-end stores await you.

One of the best things to do on your last day is to explore 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.

Unwind and look back at the past 9 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Madrid or just grab something light to keep you going.

Have a fantastic dining experience at Prada a Tope Madrid, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Restaurante Morgana offers an enticing alternative with its varied 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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