Madrid & Toledo: Spain Tour

A 5 day trip to Spain 
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Open your eyes to the beauty of Spain. The awe-inspiring art, magnificent monuments, convivial culture, and unbelievable nightlife will dazzle you. Celebrate the moment and discover the country’s grandiose past. This tour offers a wonderful insight into the fascinating contrasts of Spain. The bustling modern city of Madrid immerses you into the vibrant energy of Spanish culture, while the perfectly preserved ancient city of Toledo transports you to another era.

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Most tours are customized for private travel.

General Information

Traditional windmills in the Spainish countryside.
Detailed Itinerary

Places Visited 

Madrid and Toledo

Departure Dates 

Flexible and customizable for private departures.

Detailed Itinerary 

Day 1 - Arrive in Madrid, Spain

The tour begins with your arrival at the Madrid airport. To ensure that you have a stress-free start to your vacation, you’ll be greeted at the airport by your driver who will provide a private transfer to your hotel. Today after you’ve checked in to your hotel and have taken some time to relax, you can begin your discovery of Madrid. 

Spain was the most powerful country in the world in the 16th and 17th centuries—during the Age of Exploration. As Spain’s capital city, Madrid became the center of the world. Although the Spanish empire declined in following centuries, Madrid has recently reemerged as a great city. Ever since Spain joined the European Union, there has been a renaissance of culture and cuisine in Madrid. The city boasts world-class art museums, from the Museo Nacional del Prado that was created as the Royal Museum of Painting and Sculptures for King Ferdinand VII, to the Museo Thyssen-Bornemisza that opened in 1992 to display two remarkable private art collections. There are also many new culinary landmarks where you can sample the finest, most innovative Spanish gastronomy. 

Madrid is a lively place to visit and tapas is one enjoyable tradition that you can’t miss. The Spanish equivalent of the American happy hour or pub-crawl, meeting for tapas is a casual social gathering. Friends may decide to meet at a bar in the late afternoon or early evening to enjoy a glass of wine. In Spain, wine is always accompanied by “tapas,” small snacks such as fried anchovies, specialty ham, canapés and olives. Ask the locals where to go and experience the Spanish social life from an insider’s point of view. The Madrilenos are friendly and open people, and you’ll find it’s easy to strike up a conversation even though it’s a big city. Immersion into the culture becomes more interesting when you get to know the people.

Day 2 & 3 - Guided Tour of Madrid’s Habsburg Quarter & Afternoon at Your Leisure

Today after breakfast at your hotel, set off for a private guided tour of Madrid’s historical Habsburg Quarter. The Habsburg dynasty ruled Spain from 1516 to 1700 and presided over a global empire, with Madrid as their capital. You’ll begin at the Puerta del Sol, the vibrant plaza that is the heart of Madrid. Then you’ll wander the elegant streets of this regal neighborhood to appreciate the beautiful architecture. Habsburg buildings are distinguished by brick and granite façades with balconies, corner towers and slate spires. You can see the architectural influence of Austria, where the Habsburg family originated. The tour includes a visit to the breathtakingly immense Royal Palace that was inspired by the Louvre Palace in Paris. Seeing the grandeur of this palace allows you to understand that Spain was once a super power. A tour through the lavish interior of this palace shows you the wealth of the Spanish empire in the 16th century. Admire the masterpieces of art by Tiepolo, Goya and Velázquez. Take in the splendor of the Hall of Mirrors that rivals the exquisite hall of Versailles Palace. 

After your guided tour, the rest of the afternoon is at your leisure. You may want to continue sightseeing at your own pace. Stroll along Madrid’s impressive boulevards and fashionable side streets and stop at the beautiful public squares. Those who enjoy shopping should visit the fashionable Barrio de Salamanca, which is Madrid’s most chic and exclusive district. For art lovers, the Museo del Prado is an absolute must! This world-class museum houses the most important collection of Spain paintings in the world. The galleries hold more than 4,800 paintings, including the masterpieces of El Greco, Goya and Velázquez. The Goya section alone displays 140 paintings. While the Museo del Prado focuses on art from the great Spanish masters, the Museo Thyssen-Bornemisza displays a wide range of art genres. A compilation of two exceptional private collections, the Museo Thyssen-Bornemisza displays renowned works of art from the medieval era to Rococo and Impressionism. Another highly recommended tourist attraction is in an unlikely location, at a former convent of barefoot Franciscan nuns. The Convento de las Descalzas Reales was once a part of a royal palace and became a convent in 1557. Despite the uninviting exterior, this convent’s ornate interior boasts masterpieces by Titian, Brueghel and other renowned artists along with an exceptional collection of tapestries based on Rubens drawings. The tapestries are so exquisitely detailed that four or five artisans were required to weave just one square meter over one year. After sightseeing, be sure to save time for a siesta or at least to freshen up before the evening. 

The evening is when Madrid truly comes to life. Tonight is your opportunity to experience Madrid’s amazing nightlife and sample the exceptional cuisine. Some restaurants combine dining with nightlife, such as La Terezza restaurant at the Casino de Madrid, an exclusive private club. La Terezza offers an amazing dining experience in a glamorous Belle Epoque setting. This highly acclaimed two Michelin-starred restaurant features avant-garde Spanish gastronomy. La Terezza’s cuisine has been described as “lighthearted” and “original.” The chef prepares his own interpretation of classic tapas recipes and the results are unforgettable. The special degustation tasting menu includes the restaurant’s signature dish called “Kellogg’s Paella,” prepared from Rice Krispies, shrimp and vanilla-infused mashed potatoes. For another type of truly special dining experience, the Biblioteca restaurant is highly recommended. Located in what was once the library of the Duke of Santo Mauro, this intimate restaurant only accommodates 30 dinners and allows you to soak up the ambience of another era. The beautiful dining room features an antique fireplace and cherry wood paneled walls. In summer, you may enjoy cocktails on the terrace overlooking the lovely Santo Mauro garden. Despite the old-fashioned setting, the restaurant focuses on modern Spanish cuisine and offers delightfully imaginative dishes. 

If you’re interested in this type of fine dining experience, you should reserve ahead of time. However, gourmet dining may not be your preference. For a more casual culinary experience, you can try the typical Spanish custom of tapas. It’s not meant to be a complete meal, tapas are snacks to tide you over between meals (although if you eat enough, tapas will suffice). The word “tapas” means “cover” and the custom began as a snack for country field workers. The plate was used as a cover to protect the wine from flies, and eventually it became a tradition to use the plates to serve small bites. In Madrid, the tapas experience is more convivial than rustic and you’re likely to find gourmet appetizers like Serrano ham, chorizo sausage or fried anchovies.

Day 4 & 5 - Guided Visit to Toledo, UNESCO World Heritage Site

After breakfast at your hotel, you’ll take the high-speed train from Madrid to Toledo. When you arrive at the Toledo train station, your local guide will greet you and you are sure to be immediately awed by the city’s unique beauty. Even the train station is a lovely building that pays tribute to the city’s architectural heritage. The station was designed in the characteristic Neo-Mudéjar style, influenced by Islamic designs of old Moorish buildings. Your guide will lead you from the train station to the historic city to Toledo, which has been designated in its entirety as a UNESCO World Heritage Site. It is quite rare to have an entire city receive this UNESCO designation. However, Toledo is a special case. Toledo is one of the Spanish cities with the greatest wealth of monuments: palaces, fortresses, mosques, the medieval quarter with magnificent gothic cathedral, and the old Jewish Quarter with medieval synagogues.

Your sightseeing tour begins at the impressive ancient gateway of Puerta Bisagra, built by the Moors in the 6th century and crowned by the city’s imperial coat of arms. Toledo was an important Moorish city until the 10th century. However, in 1085 Toledo became a capital of Christian empire of Spain under King Alfonso VI. Toledo became an important medieval city. In this era, Toledo became a city of three religions groups: Christians, Muslims and Jews. Toledo is a city well-known for its religious tolerance and peaceful coexistence in Spain. Next you’ll visit the Alcázar, the ancient Moorish palace that was redesigned as a Christian royal residence for King Carlos I. Finally visit the spectacular gothic cathedral that is filled with priceless works of art. The renowned painter El Greco lived most of his life in Toledo and produced exceptional masterpieces that are on display in Toledo’s cathedral. You’ll have a chance to wander the city’s maze of narrow cobblestone streets that take you on a winding journey back in time. Everywhere you turn, you’ll stumble upon an important historic monument.

After the tour of Toledo, you’ll enjoy an excellent lunch in one of the best restaurants in the city. Then you’ll take the high-speed train to return to Madrid by the late afternoon. You’ll have the evening at your leisure in Madrid. You may want to have dinner at a restaurant near your hotel, so that you can also go out on the town. Take advantage of Madrid’s incomparable nightlife. Get tickets to see a Flamenco show, listen to live music at a club or check out one of the city’s stylish jazz lounges. 

Day 6 - Day of Leisure

You can take this day to tour more of Madrid at your own pace. If you're a student of art or into world-class gastronomy, Madrid has no shortage of experiences to impress. As Madrid is one of the gastronomy capitals of Europe and where chefs go to eat, many travelers have enjoyed visiting a few renowned tapas bars and restaurants, namely Botín, known for serving timeless dishes that you can easily say is authentically of Madrid. Or, try La Corral de la Morería, famous for its classic dishes.  They also have one of the best Flamencos in the city to end the perfect evening.

Madrid is also famous for its collection of world famous art. If you didn't get a chance to visit the museums, now is your chance!  The Prado Museum is a popular destination for tourists and locals alike as it houses the masterpieces of Goya and Velasquez, Madrid's two native sons. The Thyssen-Bornemisza Muesum also boasts an impressive collection of priceless art with over 1000's of unique pieces from artists like Rothko and Picasso. The Reina Sofia Museum has collections of the famous contemporary art works by artists Miro and Dali.

Day 7 - Tour Concludes with Departure from Madrid

The tour concludes today after breakfast at your hotel. You’ll be provided a private transfer to the airport and departure for your return flight home. Alternatively, you may want to consider a customized tour extension to the vibrant city of Barcelona or the sunny beach towns of Costa del Sol.


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.