Grand Journey to Spain & Portugal

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

Set-off on a grand tour through Castilian Spain and the heart of Portugal on an epic journey that will take you from the legendary countryside of Salamanca and banks of the Douro River, to the cosmopolitan centers of Madrid, Porto and Lisbon. Fine art, gastronomy, medieval hilltop villages, and the romance of the Atlantic coast await in this celebration of Spanish and Portuguese culture.

Sample Itinerary

Day 1

Be welcomed at Madrid Barajas Airport by your chauffeur and depart for the cosmopolitan center of magnificent Madrid, where you will check-in to your chic, five-star hotel housed within a former palace from the early 20th century. Enjoy an epicurean start to your Encounter with a unique tapas tasting tour led by a local food expert. Experience Madrid's lively Chamberi district as you savor tapas, both traditional and contemporary, at the city's most revered tapas bars along famed gastronomic street, Calle Ponzano.

Day 2

Begin the morning with an exclusive private visit of the acclaimed Thyssen-Bornemisza Museum, where a resident art docent will guide you through the museum’s intriguing permanent collection of art spanning from the 13th to the late 20th century. Visit the tranquil green space that is Buen Retiro Park punctuated by a central lake where romantic row boats while away the day, before savoring a lunch of Castilian fare alongside local Madrileños at a historic meson. Experience Madrid’s oldest district, the Los Austrias quarter, for a sense of how the city felt during the Hapsburg reign with its grand architecture and beautiful civic spaces like Plaza Mayor and end the day with a sweet repose of classic churros con chocolate.

Day 3

Depart your sophisticated city stay in Madrid for the UNESCO world heritage site of El Escorial. With your local expert you’ll explore the intricacies of this iconic 16th century complex, comprised of a royal palace, monastery, basilica, library, and college. Be chauffeured to the ancient city of Salamanca to discover the charms of its UNESCO Old City, home to Spain’s oldest university dating back to the 13th century, and the stunningly Baroque Plaza Mayor. Lunch will be enjoyed at a historic restaurant noted for its traditional flavors and elegant service, before admiring the Gothic and Baroque architecture of the city’s Catedral Nueva built during the 16th and 18th centuries. This evening, you’ll check-in at your stunning five-star hacienda nestled in Salamanca’s wine country.

Day 4

Travel deeper into the sweeping Salamanca countryside, where you’ll spend the day visiting your hacienda’s very own organic farm. Learn about the estate’s sustainable farming techniques while visiting its idyllic vegetable garden and enjoying a leisurely walk along scenic nature trails. Your day at the farm will culminate with a tasting of estate produced Jamon Iberico and embutidos, golden olive oil and sheep’s milk cheeses, before returning to the hacienda for an afternoon at your leisure. Tonight you will dine on contemporary Castilian cuisine paired with the hacienda’s signature wines, within the private setting of the estate’s exclusive wine cellar.

Day 5

Today you will bid farewell to España and travel into neighboring Portugal. Stop to explore the medieval fortified village of Bragança to admire its 12th century Romanesque town hall and 13th century Castle of Bragança. Delight in a lunch of local specialties, before being chauffeured to the UNESCO World Heritage vineyards of the majestic Douro Valley for check-in at your sumptuous, five-star wine country retreat. In the evening, delight in exquisite views of the river as you sample the region’s signature Port at one of the region’s most storied quintas.

Day 6

Privately cruise along the Douro River aboard an authentic wooden Rabelo Boat, as your knowledgeable captain describes the Rabelo’s significance in the historic production of Port. For lunch, be dazzled by splendid riverfront views as you savor a tasting menu of contemporary Portuguese cuisine with wine pairing at one of the region’s most exciting gastronomic restaurants. Spend the afternoon discovering stellar reds like Touriga Nacional and Tinta Roriz while taking in dramatic views of the Douro vineyards at two of the region’s most esteemed producers.

Day 7

From your serene Douro River retreat set off for the medieval town of Guimaraes to explore its magnificent UNESCO designated center with your local guide. Journey back to the middle ages as you encounter the 10th century Castelo de Guimarães and such sublime civic squares as the Largo da Oliveira and Largo de São Tiago with their historic wooden houses and balconies typical of Northern Portugal. Dine on modern interpretations of regional specialties at a chic gastronomic restaurant before traveling to the ancient Roman city of Braga for an insider’s look at the Baroque masterpiece, the Santuário do Bom Jesus do Monte, known for its unique zig-zag staircase, adorned with intricate sculptures and fountains. Tonight check-in to your sophisticated five-star stay in the center of Porto’s historic heart, and celebrate local flavors with an elegant dinner at the city’s most clandestine gourmet treasure.

Day 8

Get acquainted with the authentic sights and sounds of Porto with your expert guide. Discover the city’s historic downtown, the Baixa, from the architectural splendor of the Avenida dos Aliados and Clerigos Church to the spectacular Azulejos of the São Bento train station and Belle Epoque enchantment of a fabled cafe. Visit the Morro da Sé neighborhood with its Romanesque Sé do Porto (Porto Cathedral), before touring the sinewy medieval streets of the Ribeira district, leading to colorful Praça da Ribeira, with its enchanting riverfront of colorfully whimsical houses. Travel across the Dom Luís I Bridge to Vila Nova de Gaia for a gourmet lunch featuring panoramic city views at an esteemed Port wine house. This afternoon you’ll uncover the finest Ruby and Tawny Ports with a vertical tasting at a distinguished cellar.

Day 9

From the vibrant splendors of Porto depart for a treasure of the middle ages, the hilltop town of Coimbra, a tumble of glorious medieval neighborhoods spiraling toward the 13th century University of Coimbra. Your local expert will lead you through its Baroque Chapel of São Miguel and 18th century Biblioteca Joanina housing over 300,000 books within its series of opulent gilded bookcases. After lunch in the town’s scenic center of winding stone stairways and antique dwellings, be chauffeured to one of central Portugal’s most ancient towns, Tomar, a former Roman settlement turned 12th century stronghold of the Order of the Knights Templar for a guided visit led by a local expert. Set off for Portugal’s vibrant capital of Lisbon for check-in to your chic, five-star stay nestled within one of the city’s most stunning neighborhoods. Tonight you will experience the soulful saudade of the nation’s most enthralling musical artform at an authentic Fado house.

Day 10

Your expert guide will welcome you with a private exploration of Lisbon’s historic Baixa district, with time to admire its exquisite Pombaline splendors, such as the Praça do Comércio and Pedro IV Square, commonly known as Rossio Square, an important center since the medieval period. Enjoy an enchanting ride up the statuesque Santa Justa lift, a Neo-Gothic vision in iron, for panoramic views overlooking the Baixa district, Castle of São Jorge and Tagus River in the distance. Dine at one of the city’s most exciting gourmet eateries for lunch, then discover the atmospheric Barrio Alto with its narrow sloping streets, 16th century architecture and distinctly Bohemian vibe.

Day 11

Discover Lisbon’s elegant Chiado district with a free morning to shop along its graceful avenues of upscale boutiques and antique cafes. Be chauffeured to a former 17th century fortress nestled along the majestic Atlantic coast, for a Michelin-starred lunch of innovative dishes inspired by Portugal’s coastal bounty. Next depart for the former fishing village turned sumptuous resort town of Cascais, for free time to meander along its breezy waterfront promenade and discover the cobblestone streets of Old Town with its 19th century charms. Following your chauffeured return to Lisbon, enjoy a free evening to celebrate your journey through Portugal.

Day 12

Bid Adeus to Lisbon as you are chauffeured to Lisbon Airport for departure.

Experiences We Recommend

  • Private docent-led visit of Thyssen-Bornemisza Museum in Madrid
  • Guided exploration of the UNESCO designated El Escorial the former residence of the King of Spain
  • Visit to the oldest university of Europe in Salamanca and the city's Roman bridge
  • Organic farm visit for overview of sustainable farming with jamon iberico tasting
  • Private rabello boat tour along Douro River
  • Exclusive private winery tours and tastings in Douro Wine Country
  • Privately guided visit of historic cities of Guimaraes and Braga
  • Traditional azulejos workshop led by local artisan in Porto
  • Visit to quaint fishing village outside Porto to experience local coastal cuisine
  • Premium port cellar visit and tasting in Porto
  • Visit of Porto Cathedral and city’s oldest quarter, the Morro da Sé
  • Guided tour of UNESCO heritage city of Coimbra
  • Fado music performance in Lisbon
  • Michelin-starred dining experience in seaside village of Cascais


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

  • Gay B.

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