Cellars & Kitchens of Castilian Spain

Encounter Spain

Delve into the singular gastronomy and fabled wine culture of Castilian Spain as you are introduced to the winemakers blending old world varietals into velvety vintages of note, while sipping your way through through boutique Tempranillo and Verdejo vineyards in Toro and Rueda, and the legendary bodegas of Ribera del Duero. Savor rustic Manchego in La Mancha, and sample prized jamon iberico and handcrafted embutidos in Salamanca, as your culinary journey takes you from organic olive oil producers preserving sustainable farming techniques to the truly local mercados and legendary tapas bars of Madrid.

Trip Details

10 Days / 9 Nights

Day One

Your culinary adventure through Castilian Spain will begin with arrival to Madrid Barajas Airport or Puerta de Atocha Train Station and a warm welcome from your awaiting chauffeur. Set off for the UNESCO World Heritage center of Toledo for arrival to your historic, boutique luxury hotel, Entre Dos Aguas Hotel Boutique, former residence of iconic flamenco guitar maestro Paco de Lucia. Toast to the start of your epicurean adventure with a dinner of contemporary La Mancha fare based in tradition at one of the city’s most exciting gastronomic restaurants.

Stay: Entre Dos Aguas Hotel Boutique
Meals: Dinner

Day Two

Start the day at the countryside farm of an artisan cheese producer to discover how La Mancha’s coveted Manchego is crafted, before delighting in a tasting of the producer’s fine curado and semi-curado cheeses. Set off for the legendary twelve windmills of Consuegra’s picturesque Calderico Ridge, immortalized by Cervantes in his literary masterpiece, Don Quixote, as your CB Regional Ambassador elaborates on their cultural significance and historical legacy. A lunch of reinterpreted Manchegan cuisine hosted at a scenic estate awaits you in the sprawling countryside of Toledo followed by a guided afternoon in Toledo. Admire El Greco’s triumphant masterpiece, The Burial of the Count of Orgaz, in the Church of Santo Tomé and embark on a private walking tour of the city’s medieval Jewish Quarter to learn about Toledo’s history as an ancient center of Sephardic life and culture in Spain. Visit the 13th century Cathedral of Toledo to appreciate the intricacies of its Gothic and Mudejar architecture, before having a glimpse into the city’s ancient past with a visit to an underground site not normally open to the public. Tonight you’ll delight in a lively introduction to the flavors of Toledo with a tapeo (tapas tasting walk) through the heart of the historic center.

Stay: Entre Dos Aguas Hotel Boutique
Meals: Breakfast, Lunch, Dinner

Day Three

Today travel to the sweeping landscapes of the La Mancha countryside to appreciate gifts from its sun kissed terroir. Embark on an owner-led walk through the historic olive groves of their organic estate to learn about sustainable olive oil production, before enjoying an al fresco tasting of the producer’s artisan Extra Virgin Olive Oil and a light lunch of locally produced gourmet products. Next, set off for an esteemed wine estate in Tierra de Castilla Wine Country for a private tour of their historic barrel room and an exclusive tasting of the winery’s stellar Castilla La Mancha DO wines made from varietals such as Cencibel, Syrah, Tempranillo and Cabernet Sauvignon. This evening spend free time exploring Toledo at your leisure.

Stay: Entre Dos Aguas Hotel Boutique
Meals: Breakfast, Lunch

Day Four

From Toledo your chauffeur will transport you to the UNESCO World Heritage old town of Ávila. An architectural feast for the eyes, from Romanesque and Gothic to Renaissance, your CB Regional Ambassador will help you explore its perfectly preserved medieval walls and historic treasures, such as the Puerta de San Vicente, 12th century Gothic Cathedral of Ávila, and Plaza Mayor. Stop at a historic confectionery for a taste of the local delight, Yemas, before traveling onward to the ancient city of Salamanca. Savor lunch of classic dishes reimagined with a modern twist at a storied mesón, before discovering Salamanca’s oldest quarter, a UNESCO World Heritage site, including the glorious Plaza Mayor and illustrious university buildings dating back to 1218. Take a moment to sample typical embutidos (cured sausages) indicative of the region at a specialty purveyor, before traveling to your 14th century monastery turned five-star luxury stay, Hacienda Zorita Wine Hotel & Spa, nestled in Duero Valley vineyards of Salamanca.

Stay: Hacienda Zorita
Meals: Breakfast, Lunch

Day Five

Spend the morning in the majestic dehesa as you experience Hacienda Zorita’s organic farm first hand. Embark on an exciting 4×4 ride through the sprawling meadows of the estate, followed by guided visit of the farm to learn about their cultivation of fresh produce, culminating with tasting of the estate’s handcrafted artisan products, such as prized jamon, limited edition vinegar, and rustic cheeses. Following your morning in the dehesa, have free time to enjoy the delights of your bucolic country estate, or perhaps spend the afternoon relaxing at Zorita’s Wine & Olive Spa. Tonight enjoy a multi-course winemaker’s dinner of contemporary Spanish cuisine with Sommelier-led wine pairing hosted within Hacienda Zorita’s historic cellar.

Stay: Hacienda Zorita
Meals: Breakfast, Dinner

Day Six

Depart the dehesa of Salamanca for the Toro wine appellation of Zamora, where you’ll be welcomed for a private bodega visit and tasting flight of prestigious vintages at an acclaimed estate renowned for its production of what is considered the region’s most highly regarded DO Toro wines. Travel to the Rueda Wine Route of Valladolid for an exclusive visit of the vineyards and historic aging cellars of a boutique wine estate owned by a sixth generation winemaking family, followed by a tasting of their signature DO Rueda wines crafted from the local Verdejo grape varietal, alongside local gourmet products. Be chauffeured to Ribera del Duero’s Golden Mile for arrival to your sumptuous, five-star wine estate, Abadia Retuerta LeDomaine, and free time to get acquainted with your serene vineyard setting. Tonight you can look forward to a special tasting menu comprised of modern Spanish creations paired with estate produced wines at the hotel’s acclaimed Michelin-starred restaurant, Refectorio.

Stay: Abadia Retuerta LeDomaine
Meals: Breakfast, Light Lunch, Dinner

Day Seven

Start the day with an exclusive wine experience at the Abadia Retuerta estate. Embark on an exciting private 4×4 tour of the estate vineyards for an introduction to the cycles of the grapevine. Continue with a private visit of the Preparation and Barrel Rooms, before enjoying a guided tasting flight from the estate’s celebrated Winemaker’s Collection. Travel next to the legendary estate of a preeminent Ribera del Duero winemaking dynasty, for a private visit and tasting of their high quality Reservas made from Tinto Fino Tempranillo grapes. Arrive to the modern-style cellars of an acclaimed producer celebrated for their contemporary sensibility and innovations in winemaking, where you’ll savor an inventive multi-course lunch paired with a tasting flight of estate wines. Crown the afternoon with a visit to the historic town of Peñafiel to appreciate its impressive Plaza del Coso with the inspiring backdrop of Peñafiel Castle in the distance

Stay: Abadia Retuerta LeDomain
Meals: Breakfast, Lunch

Day Eight

From the heralded vineyards of Ribera del Duero set off for the cosmopolitan heart of Madrid, the Spanish capital. Arrive to your sophisticated five-star stay, Urso Hotel, housed within a former palace from the early 20th century, and be welcomed by your CB Regional Ambassador who will introduce you to the vibrant culture and cuisine of Madrid. Embark on a guided visit of the jewel box Museo Nacional Thyssen-Bornemisza to admire its comprehensive collection of art masterpieces spanning from the 13th to the 20th century, including works by such artists as El Greco, Caravaggio, Manet, Picasso, Dali and more. For a true taste of the city, enjoy a food focused exploration of Calle Huertas in the Barrio de Las Letras neighborhood, known by the locals as one of the best places to savor the most typical flavors of Madrid. Stop for a refreshing aperitif at a bar with distinctly Madrileño flair, enjoy artisanal delicacies at a historic purveyor of fine foods and wine, before sampling typical raciones at a fabled taberna. Your afternoon will be spent discovering the scenic plazas of the Barrio de Las Letras and Los Austrias quarter, including the glorious Plaza Mayor, before relishing traditional churros con chocolate at a legendary cafe

Stay: Hotel Urso
Meals: Breakfast, Lunch

Day Nine

This morning be greeted by a local food expert who will help you experience one of the city’s most epicurean markets to procure a delicious selection of regional ingredients, while learning about their role in typical Castilian and Spanish cuisine. Fresh from the market to the plate, roll up your sleeves for a private, hands-on cooking class of traditional Castilian dishes under the tutelage of a professional chef, culminating with a lunch of your delicious creations and regional wine. The rest of the day will be free to continue discovering Madrid’s many sites and sounds at your leisure.

Stay: Hotel Urso
Meals: Breakfast, Lunch

Day Ten

Bid adios to cosmopolitan Madrid and depart by chauffeur for either Madrid Barajas Airport or Puerta de Atocha Train Station for departure, and the end of your Encounter.

Meals: Breakfast


The price of this Crafted Encounter begins at $10,350/per person*, based on double occupancy and a travel party of two.  

Groups of four or more are eligible for our small group preferred pricing, and will enjoy 25% off the total trip price. 

*The price of your Crafted Encounter will be determined by your travel party size and requested dates. This Encounter is also available for solo travelers at an additional cost.


A seamless travel experience from arrival to departure

Firsthand local knowledge & insights by our expert team

24/7 support during your Encounter

Chauffeured, private transportation for touring & transfers

Private touring with our professionally licensed & English speaking Regional Ambassadors

Stays at five & four-star boutique luxury accommodations

Engaging activities led by our family of cultural experts

Signature experiences with insider access

All tickets/entrance fees associated with touring

Organized dining experiences celebrating regional cuisine

Traveler Welcome Package

Taxes & base gratuities

Not Included

International or regional airfare

Airport taxes and charges, airport parking or excess baggage charges

Expenses for activities/excursions not included or identified in the Encounter itinerary

Transportation expenses incurred during free time

A-la-carte food orders, alcoholic beverages or wines outside of pre-arranged menus during organized meals

Any meals or beverages during free time

Personal expenditures and personal spending money

Hotel incidentals including room service, laundry services and hotel bar tabs

Hotel room upgrade requests and/or fees/supplements incurred from any room changes

Travel insurance including health, accidents, lost baggage and trip cancellation

Passport and Visa expenses

All other items that are not mentioned or included in your Encounter itinerary

Requesting Dates

Once you submit your Booking Request, our team will get to work confirming whether your preferred travel dates are available. Within 72 hours of receiving your Booking Request, we will provide you with a quoted trip price for your preferred dates and travel party size, along with booking instructions that will include steps on how to submit your required trip deposit.

Why is my quoted trip price different than the published starting price per person?

While our Crafted Encounters are pre-designed and ready to book travel experiences, there are important factors that may impact the quoted trip price, namely hotel availability, number of travelers in your party, and whether you are requesting to travel during high or low season in a specific region or during a national holiday/special event.

What happens if my requested travel dates are not available?

Should your requested travel dates not be available, or if they happen to encompass a national holiday or special event that will significantly impact your quoted trip price, we will certainly let you know and work with you to identify alternate travel dates.

Months Offered

Year Round

Arrival & Departure

This Crafted Encounter includes a chauffeured private transfer from Madrid Barajas Airport or Puerta de Atocha Train Station upon arrival, and a chauffeured private transfer to Madrid Barajas Airport or Puerta de Atocha Train Station for departure.

Private transfers to and from alternate locations not included as part of this Crafted Encounter, such as a residence, hotel, car rental office, etc., can be requested at an additional cost.

Handpicked Stays



Entre Dos Aguas Botuique Hotel


Hacienda Zorita


Abadia Retuerta LeDomaine


Hotel Urso

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Interested in a 100% tailor-made experience?
Perfectly handcrafted just for you. Our Couture Encounters are artfully designed start to finish according to your cultural interests, preferred travel pace, and ideal length.
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Booking Request
Our collection of private and expertly pre-designed Encounters are meant to awaken your inner traveler, immerse you in rich regional culture, and capture the nuances that make for exceptional travel experiences. Now that you’ve fallen in love with your ideal trip, it’s time to request your dates and tell us a little more about your travel party. Within 72 hours of receiving your booking request, we will let you know if your dates are available, and provide you with booking and deposit payment instructions. So now it’s time to sit back, relax, and let us do the rest!
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Our Encounters are private trips meticulously designed to be seamless experiences, from deluxe accommodations with character and chauffeured transport to knowledgeable local experts and engaging activities. Can’t decide between a pre-designed Crafted itinerary or a fully tailor-made Couture experience? Your next great adventure is just moments away!

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