Into the Heart of Madrid & La Mancha

Into the Heart of Madrid & La Mancha

Experience the prolific history and rich culture of Spain’s Castilian heart with a journey through its vibrant capital Madrid and the surrounding provinces. Savor your way through the city’s beloved Mercado de San Miguel before exploring its esteemed art museums, architectural marvels and the region’s  folkloric musical traditions. Examine the historical treasures and unique heritage of Toledo before uncovering Castile’s noble legacy in San Lorenzo de El Escorial.

    Into the Heart of Madrid & La Mancha

    Sample 5-Day Private Trip Itinerary

    Madrid, Toledo, San Lorenzo de El Escorial


    Day 1

    royal_palace_of_madrid_spain_private_tour_countrybredUpon arrival in Madrid, be greeted by your private chauffeur and be transported to your deluxe four-star hotel located on Madrid’s famed Gran Via. Make your way to the bustling Mercado de San Miguel where you will enjoy a guided gastronomy walk. Sample your way through the market’s cornucopia of artisanal cheeses, olives, charcuterie and sweet confections. Afterward, partake in 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

    prado_museum_madrid_spain_private_tour_countrybredBegin your day by experiencing the illustrious Prado Museum, where you will admire master works by Velasquez, Goya and Titian, among countless others, under the guidance of a resident art expert. Spend the rest of the afternoon enjoying Madrid at your leisure with free time to explore its iconic plazas and boulevards like the Plaza Mayor, Plaza España, Puerta del Sol and the Plaza de Oriente. In the evening, experience the passion of Flamenco while you savor typical Madrileño tapas at one of the city’s most celebrated Tablaos.

    Day 3

    toledo_spain_tour_countrybredDepart for a scenic drive of La Mancha’s countryside 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, Synogogue de El Transito and El Greco’s triumphant Burial of the Count of Orgaz in the church of Santo Tomé. Stop for a lunch of Toledo’s signature dishes including venison stew and other local specialties at a historic eatery. In the afternoon, explore Don Quijote’s windmill route in the province of Consuegra before returning to your hotel in Madrid for a free evening.

    Day 4

    plaza_mayor_spain_private_tour_countrybredSpend a free day soaking in Madrileño life shopping at the city’s many boutiques or admiring art at the Reina Sofia Museum, which houses Spain’s most coveted 20th century masterpieces. End your day with an elegant farewell dinner of creative Spanish cuisine at a Michelin starred restaurant in the city center.

    Day 5

    Depart Madrid for your return flight home or the next leg of your trip.

    – As part of our Enriched Booking process your customized itinerary will be designed with the assistance of a CountryBred specialist.
    – This trip can be specifically tailored for organizations, associations and corporate incentives.


    The recommended trip length for this sample itinerary is 5 days/4 nights with pricing options beginning at $3,250/person based on double occupancy. Please note that the “Share Bred With Friends” preferred pricing program will be applied to travel parties of four or more.

    The final price of your custom trip 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.

    Included in this sample CountryBred Encounter are:

      • 4 Nights at CountryBred approved, four-star boutique accommodation
      • Deluxe and/or Superior room stays
      • Chauffeured luxury transport for all intercity travel, day trips and excursions
      • Airport / Train station transfers with baggage assistance
      • Private touring with professionally licensed local guides and cultural experts
      • Flexible guided time with local experts based upon your preference
      • 3 Gourmand dinners
      • 2 Regionally authentic lunches
      • Daily breakfasts
      • Museum tickets & entrance fees
      • All gratuities & taxes
      • Traveler welcome package including customized Culture Guide
      • Please note that transfers to airports other than Madrid Barajas for arrival/departure are available upon request for an additional, supplemental fee. Airfare is not included.

    Featured Deluxe Hotels

    hotel-de-las-letras-madridHotel de Las Letras ****

    A boutique luxury hotel located on Madrid’s illustrious Gran Via, Hotel De las Letras is a historic fixture of this grand boulevard. The building in which the hotel is housed dates back to 1917 and included in the city’s prestigious heritage register. Originally created by architect Cesáreo Iradier as the home of the Count of Artaza, the property was renovated for use as a hotel in 2005 by architects Virginia Figueras and Franco Corada.

    Encounter Something Unexpected

    Experiential travel takes time, passion and local ingredients to make something truly special. When you travel with CountryBred, you can look forward to the following:

        • A personalized and private travel experience, whether you’re a solo voyager, a couple, group of friends, family or an organization


        • A well crafted itinerary that is a reflection of your cultural interests, which we bring to life through our unparalleled insider knowledge, local access and dedicated team


        • A thoughtful travel pace that leads you down roads less traveled while leaving time to enjoy the quiet moments that make for remarkable memories


        • Enriching activities that immerse you in local culture and traditions


        • Premium accommodations that are distinct reflections of the regions they reside in, with real histories and real people behind them


        • Regional ambassadors and local cultural experts that go beyond educating, to invite you into their community and introduce you to their unique corner of the world.


      • Authentic dining that ensures you enjoy the finest in regional culinary traditions from quaint family owned eateries to innovative Michelin-starred restaurants. Each meal is in itself a work of art, passionately prepared and uniquely local.


    Authentic is Premium