Into the Heart of Castilian Spain

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
  • Custom Quote

Encounter a land rich with medieval castles, noble palaces and stunning wine country on this voyage through Central Spain. Your cultural exploration will take you to Europe’s largest royal palace and to the UNESCO heritage burgs of Avila, Salamanca and Segovia, before welcoming you to the illustrious vineyards of Ribera Del Duero.

Sample Itinerary

Day 1

Upon arrival in Madrid, be welcomed by your private chauffeur and transported to your luxury five-star hotel located just steps from the Thyssen-Bornemisza and Prado museums. After settling in, embark on a privately guided visit of Madrid’s Royal Palace, Europe’s largest royal palace, with a local expert. In the evening, dine at the world’s oldest known restaurant where you’ll indulge on their renowned suckling pig and roasted game, as well as other typical dishes prepared in the traditional Castilian way.

Day 2

Depart on a scenic train ride to the UNESCO world heritage site of Toledo, rich in Christian, Jewish and Moorish influences, architecture and cultural treasures. Your local expert will take you on a unique walking tour of the city’s hidden streets, while stopping along the way to visit its marvelous Gothic Cathedral and Synagogue de El Transito. Stop for a lunch of Toledo’s signature dishes at a historic eatery. In the afternoon, admire El Greco’s triumphant Burial of the Count of Orgaz in the church of Santo Tomé, before visiting the Monasterio de San Juan de Los Reyes. End your day with a sampling of Toledo’s typical marzipan confections, a treat descended from the city’s Moorish roots.

Day 3

Depart Madrid in the late morning for a scenic chauffeured drive through the countryside of Castilla y Leon. Stop at the splendid town of San Lorenzo de El Escorial and enjoy a visit to the UNESCO world heritage site of El Escorial with your local expert. Explore the intricacies of this iconic building, which remains today a functioning royal palace, monastery, school, and museum. Afterward, travel to the historic city of Ávila and enjoy an abundant lunch of typical regional dishes. Set off on a privately guided exploration of the city’s UNESCO honored historic core, including the Puerta de San Vicente, 12th century Gothic Cathedral of Ávila, and perfectly preserved medieval walls. From Avila you will continue on to your stunning five-star hotel nestled in Salamanca’s wine country.

Day 4

Spend the day visiting the ancient city of Salamanca with your local expert. Explore the oldest part of the city, declared a UNESCO world heritage site, as well as Salamanca's illustrious university, which dates back to 1218. Savor a lunch of regional delights at a historic restaurant in the center of town, before continuing your guided walking tour with a visit to the Tower of Clavero and Salamanca’s Roman bridge. In the afternoon, spend free time experiencing Salamanca’s charming streets at your leisure.

Day 5

Following check-out, you'll whisk away to the glorious city of Valladolid, the former 16th century capital of the Spanish Kingdom. Roam its picturesque Plaza Mayor and stop for an intriguing visit to the House of Cervantes where the noted author completed his literary masterpiece, Don Quixote. Tour Columbus’s final residence where you’ll have the chance to survey the many documents and artifacts on display pertaining to the exploration of America. From Valladolid you will travel by chauffeur to Ribera Del Duero’s Golden Mile for check-in to your historic five-star wine estate. Enjoy a horseback ride through the breathtaking countryside and vineyards, before indulging in an outdoor tasting of estate wines paired with local products. In the evening, delight in a special dinner of seasonal ingredients artfully prepared at your hotel's acclaimed Michelin-starred restaurant.

Day 6

Start your day off with a special wine tasting at one of Ribera del Duero’s most famed wineries, known for their high quality Reservas made from Tinto Fino Tempranillo grapes. Afterward, be transported to the town of Peñafiel where you will enjoy lunch at a historic asador. Spend the afternoon exploring Peñafiel’s 9th century castle, its medieval wine cellars, and its famed wine museum, at your leisure.

Day 7

Depart the quaint Ribero Del Duero countryside via private chauffeur for the mighty city of Segovia, a UNESCO world heritage site. Relive the city’s ancient history while touring its perfectly preserved Roman aqueduct built in 50 AD. Enjoy a private tour of the city’s Alcazar, the most important fortress of the province and onetime residence of the Kingdom of Castile’s nobility. Savor a lunch featuring the area’s celebrated olives and local charcuterie before traveling by chauffeur to Madrid for check-in to your five-star city center hotel, to enjoy a final night in the city.

Day 8

After breakfast your chauffeur will transport you to Madrid Barajas Airport, in preparation for your return flight or the next leg of your adventure.

Experiences We Recommend

  • Privately guided visit of Madrid' Royal Palace and Armory
  • Historical walking tour of Toledo including visits of the city's Gothic Cathedral, Synagogue of El Transito and El Greco's masterpiece the Burial of Count Orgaz
  • Tasting of typical Marzipan dessert
  • Guided exploration of the UNESCO designated El Escorial the former residence of the King of Spain
  • Historical tour of Avila's city center and medieval walls
  • Visit to the oldest university of Europe in Salamanca and the city' Roman bridges
  • Expert-led tour of Cristopher Columbus' final residence and the birthplace of Spanish author Miguel de Cervantes
  • Scenic horseback ride through the Castilian countryside
  • Wine tasting of premium Ribera Del Duero vintages at renowned producers
  • Historical walking tour of Sevogia's ancient aqueducts and Alcazar fortness


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Spain Encounters begins at:

  • $800-$950/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)
  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Barbara R.

    Getaway to Tuscany and Northern Italy
    CountryBred thought of every detail for our trip. We didn't have to think about or worry about anything because they had it all covered by professionals every step of the way. From the chauffeurs, to the private boats, to the ambassadors who were extremely knowledgeable and spoke good English, to the amazing hotels, to the selection of restaurants and wines...WOW!

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


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