Portugal Treasures, the Alentejo to Lisbon

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

Celebrate the culture, cuisine and history of Portugal on this elegant adventure through Lisbon and the sundrenched Alentejo. Discover sweeping landscapes of oak trees and ancient olive groves interwoven with sprawling vineyards of Aragonez and Trincadeira. Uncover the secrets of the Roman Temple of Évora and meander along the medieval streets of serene whitewashed villages, before experiencing the singular rhythms of Lisbon from soulful Fado in the Alfama to the busy hum of Remodelado trams in the Barrio Alto, and the lullaby of lapping waves as you sail along the Tagus River.

Sample Itinerary

Day 1

Be welcomed at Lisbon Airport by your private chauffeur and depart for the sweeping landscapes of Portugal’s Alentejo region. Check-in to your sophisticated, five-star country retreat and delight in a dinner of authentic Alentejan flavors within the warm hospitality of the hotel’s noted farm to table restaurant.

Day 2

Today you will uncover the historic heritage of the Alentejo, beginning with a guided visit of the ancient Roman city of Evora, an UNESCO World Heritage site. Discover the hilltop splendors of its precious whitewashed center, including the 1st century AD Templo Romano, 13th century Cathedral of Evora, and picturesque Praça do Giraldo. Sample typical Alentejo specialties at a storied eatery before traveling to a boutique olive oil mill in the countryside for a tasting of their small batch extra virgin olive oil. This afternoon you’ll explore the charming cobblestone lanes and artisan shops of the fortified village of Monsaraz, crowned by a medieval castle affording stunning views of the Alqueva Dam.

Day 3

This morning your chauffeur will transport you to one of the Alentejo’s premier Porco Preto producers for an in depth look at how this porcine delicacy is produced, followed by a tasting of the farm’s prized DOP cured ham. Set off for one of the region’s most celebrated wine estates for an exclusive vineyard visit and vertical tasting of their noted Reguengos de Monsaraz DOC wines, culminating with a gastronomic lunch of contemporary regional cuisine featuring seasonal ingredients. Your day will be crowned with an afternoon visit to a noted estate for a firsthand taste of the region’s ancient Roman tradition of producing wines in amphora pots.

Day 4

Delight in free time to enjoy a leisurely breakfast, relax at your hotel’s acclaimed spa, or lounge at the estate’s serene garden pool. At midday you’ll appreciate the natural beauty of the surrounding countryside with a guided horseback ride along idyllic trails, before savoring a scenic picnic lunch. This afternoon experience the Alentejo’s fine ceramics tradition with a hands-on pottery making lesson taught by a local artist.

Day 5

From your serene Alentejo stay you’ll set off for Portugal’s vibrant capital of Lisbon. Check-in to your chic, five-star stay nestled within one of the city’s most stunning neighborhoods. Your expert guide will welcome you with a private exploration of the 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 6

Discover Lisbon’s elegant Chiado district with free time to shop and dine along its graceful avenues of upscale boutiques and antique cafes. Be chauffeured to perhaps the city’s most majestic Miradouro for outstanding panoramic views before visiting the workshop of a local artisan to learn firsthand the art of painting authentic Azulejos tiles. Embark on a guided walk through Lisbon’s oldest quarter, the Alfama, known for its medieval labyrinth of narrow streets, charming whitewashed homes accented by intricate tilework, and historic sites like the 12th century Sé de Lisboa (Lisbon Cathedral). Tonight you will experience the soulful saudade of the nation’s most enthralling musical artform at an authentic Fado house.

Day 7

Step back in time to the age of Portuguese exploration as your expert guide leads you through the monumental district of Belem. Visit the 16th century Manueline-style fortress, the Belem Tower, an UNESCO World Heritage Site, and the Padrão dos Descobrimentos (Monument of Discoveries), immortalizing some of Portugal’s most important explorers and historical figures. Admire the uniquely mariner inspired architectural details of Jeronimos Monastery, final resting place of explorer Vasco da Gama, before embarking on your own voyage with a private sail boat tour along the Tagus River. After a leisurely free afternoon, you will enjoy an exclusive dining experience at the city's acclaimed two-Michelin star restaurant Belcanto by chef José Avillez.

Day 8

A jewel set within the forested foothills of the dramatic Serra de Sintra, today you will discover the enchanting aristocratic town of Sintra, former retreat of the Portuguese monarchs and UNESCO World Heritage Site. A celebration of 19th century Romanticism, tour the town’s stately triumphs such as the fairy-tale Pena Palace, a watercolor vision of architectural styles from medieval and Moorish to Manueline, then visit the Palace of Sintra, first constructed in the medieval period and maintained as a royal residence until the 19th century. Savor a lunch of typical Portuguese petiscos and sample Sintra’s signature pastries queijadas and travesseiros at a beloved local pastelaria, before experiencing the whimsical grandeur of the Quinta da Regaleira estate and gardens built by millionaire António Augusto Carvalho Monteiro at the turn of the 20th century.

Day 9

Be whisked away to a charming whitewashed village along the Atlantic for free time to admire its rugged coastline of dramatic cliffs, sandy beaches and frothy waves. Travel to a boutique cellar in the lesser known DOC Colares wine region for a tasting of the appellation’s covetable reds produced from the Ramisco grape, and crisp white wines kissed by the salty sea air. Dine on fresh seafood dishes at a quaint eatery before being chauffeured to former quiet fishing village turned sumptuous resort town of Cascais. Meander along the town’s breezy waterfront promenade before discovering the cobblestone streets of Old Town with its 19th century charms, and enjoy a free evening to dine at one of the many notable restaurants that can be found in Cascais.

Day 10

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

Experiences We Recommend

  • Historical walking tour of Evora including visit to ancient Roman temple
  • Private, hands-on cooking class of authentic Alentejo cuisine
  • Visit & tasting of small batch extra virgin olive oil at artisan Alentejan olive mill
  • Tasting of prized Porco Preto ham at farm of noted producer
  • Guided horseback ride through the Alentejo countryside
  • Private pottery making class of typical Portuguese ceramics with local artist
  • Private walking tour of Lisbon’s historic Baixa and Barrio Alto neighborhoods
  • Hands-on azulejo tile painting workshop
  • Private walking tour of Lisbon’s medieval Alfama & Mouraria neighborhoods
  • Exclusive performance of traditional Fado
  • Private sailboat tour along the Tagus River
  • Two-Michelin starred dining experience in Lisbon
  • Guided visit of Sintra including Pena Palace & Quinta da Regaleira estate
  • Wine tasting in coastal village of Colares
  • Guided tour of 16th century Convent of the Capuchos outside Sintra


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

Pricing for our Portugal Encounters begins at:

  • $750-$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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