Rural Portugal endures in the Alentejo: in vineyard rows, in ancestral craft, in generous sunlight. Led by our hand-picked Signature Guide, start among Lisbon’s royal quarters and journey among the whitewashed villages of Arraiolos, Monsaraz, and Vila Viçosa. Deep discovery awaits. Meet artisans preserving tradition, taste biodynamic wines with their makers, and read the night skies with an astronomer. This is rural Portugal: graceful, unhurried, golden.
Venture to the very heart of each destination on our Signature Collection, where every journey is shaped by our unrivalled local connections and insider expertise. Step beyond the ordinary with private invitations, rare encounters, and experiences few will ever share. So when someone says, “I’ve been there,” you’ll simply smile, knowing you’ve experienced it differently.
Signature Experiences
Trace constellations with an expert astronomer during a private evening of celestial discovery in the Dark Sky Alqueva Reserve
Join chef Sofia at her family farm for an immersive cookery class, preparing and sharing an Alentejano feast passed through generations
Step inside an amphora wine cellar for an intimate tasting, followed by a traditional tapas lunch that celebrates Alentejo's ancient winemaking heritage
Drift across Lake Alqueva on a private vintage boat with champagne in hand, then uncover stories of resilience at the Museum of Luz
Signature Day: Experience our distinctive Signature Day, choosing between a horseback ride across the Alentejo plains, a tile workshop in an atelier, or a guided walk along Évora’s ancient aqueduct
Signature Stay: Enjoy timeless serenity at Convento do Espinheiro, a 15th-century monastery reimagined as a luxurious retreat of cloisters, gardens, and heritage
Signature Guide: Let your hand-picked Signature guide lead you to the country’s soul – sharing their home, heritage, and heart
Activity Areas
Culture
Region & Country & City
Lisbon, Portugal
Included in the Price
- Elegant, hand-picked hotels and a Signature Stay in a 15th-century convent - All breakfasts, five lunches, and six dinners, capturing authentic Alentejano cuisine - Named Signature Guide with outstanding knowledge and guest satisfaction - Gratuities for local support staff so every detail of your journey feels effortless - Comfortable private transport for you convenience - Complimentary transfers on arrival and departure, ensuring a smooth journey
Not Included In The Price
Itinerary
Day 1 Settle into Lisbon’s rhythm | Welcome reception in a historic convent
Welcome to Lisbon, a city gilded by light where the scent of sweet pastries mingles with sea air. Settle into the Inspira Liberdade Boutique Hotel, a tranquil eco-conscious sanctuary in the heart of the city.
Complimentary arrival transfers are provided today. Those arriving early can take time to rest or join an optional private walking tour with an expert storyteller to explore elegant boulevards and uncover local life beyond the landmarks (available on request).
As evening falls, gather for our welcome reception, a refined dinner held in the graceful surroundings of the 17th-century Santa Joana Convent. Contemporary Portuguese cuisine and seasonal ingredients introduce you to the depth and warmth of local gastronomy.
Overnight at Inspira Liberdade Boutique Hotel
Day 2 Trace Alentejo’s artistry | Join celebrated vintner João Tique for a private tasting
Leaving Lisbon, we journey to Arraiolos to meet the women preserving Portugal’s hand-embroidered rug tradition. In their traditional atelier, every stitch reflects Alentejo’s soul, a centuries-old craft passed through generations. After an Alentejano lunch at O Alpendre, continue to Évora, where vintner João Tique welcomes you to his vineyard for a private tasting.
Venture behind-the-scenes to see how regenerative practices enrich the soil and foster biodiversity. Then, sip exceptional wines shaped by nature’s rhythm, often gracing Michelin-starred menus.
Continue to our Signature Stay, Convento do Espinheiro, a 15th-century convent of ancient spirituality and modern comfort. An intimate dinner awaits at the hotel’s Divinus restaurant, paired with the same wines you enjoyed among the vines.
Overnight at Convento do Espinheiro
Day 3 Step into living heritage | Private walk through UNESCO-listed Évora
A private guided tour reveals Évora’s layered past: Roman temples, Gothic cathedrals, and exclusive access to sections of the Chapel of Bones built by Franciscan monks. Each stone and square reflect centuries of faith and artistry. Lunch is enjoyed in a local tavern known for authentic Alentejo cuisine and hospitality.
The afternoon is yours to drift through Évora’s gold-stone lanes or relax in the hotel gardens. Evening dining is independent, with your Signature Guide available to make recommendations.
Second night at Convento do Espinheiro
Day 4 Follow the olive path | Cruise across Lake Alqueva in a private vintage boat
Journey to Monsaraz, Alentejo’s most timeless medieval hilltop village. A guided visit of the castle offers panoramic views over Lake Alqueva before you descend through open countryside towards the olive groves of São Lourenço do Barrocal.
Here, an olive oil experience awaits. Stroll through the family-run estate to learn age-old harvesting secrets of their native galega and bical olives, then sample olive oils during a light farm-to-table lunch.
Signature Experience: In the afternoon, enjoy a private cruise across Lake Alqueva on a vintage boat, champagne in hand. Then, step inside the Museu da Luz to discover how a displaced village found new life beyond the Alqueva dam.
Dinner follows at Convento do Espinheiro, paired with local wines.
Third night at Convento do Espinheiro
Day 5 Discover royal heritage | Create an Alentejano feast with chef Sofia
Vila Viçosa opens its doors this morning for an exclusive tour of the Ducal Palace, a masterpiece of Renaissance grandeur. Later, we meet the Flores sisters in Estremoz, whose UNESCO-listed clay dolls depict scenes of rural and religious life across Alentejo.
Lunch is served at Mercearia Gadanha, a former grocery turned contemporary restaurant celebrating inventive Alentejo dishes with warmth and flair.
Signature Experience: As evening falls, join chef Sofia Vieira at her family farm for a private immersive cooking masterclass. Together, you prepare and share a traditional Alentejan feast, celebrating rural life.
Fourth night at Convento do Espinheiro
Day 6 Signature Day | Craft, ride or explore timeless Évora
Today is your Signature Day, inviting you to connect with Alentejo’s quiet artistry and rhythm. You could:
Ride horseback through golden countryside and holm oak forests, the gentle pace revealing landscapes unchanged for centuries.
Join a local artist for a tile-painting workshop, learning traditional techniques and creating your own piece inspired by Alentejo’s patterns.
Enjoy an expertly guided walking tour, following the line of its 16th-century aqueduct through whitewashed lanes, shaded courtyards, and glimpses of everyday life behind ancient walls.
Explore Évora by e-bike, gliding between olive groves and whitewashed villages on gentle trails through the Alentejo plains.
Venture farther afield on a half-day trip to Elvas, a World Heritage city famed for its star-shaped fortifications and sweeping views across the Spanish border.
Signature Experience: As evening falls, gather beneath the vast Alentejo sky for a private stargazing experience at Dark Sky Alqueva, one of Europe’s clearest celestial reserves. Guided by an expert astronomer, watch the constellations appear with a glass of local wine in hand, a fitting finale to a day of discovery.
Fifth night at Convento do Espinheiro
Day 7 Travel through the centuries | Honour the ancient winemaking tradition of ‘vinho de talha’
An archaeologist leads a private tour of the Roman ruins of São Cucufate, revealing millennia of human connection to the land.
Signature Experience: Continue to Vila de Frades for a guided tasting of vinho de talha — wine aged in clay amphorae using methods unchanged since Roman times. At Taberna do Enteiriço, a lively tasca beloved by locals, share a traditional lunch of regional tapas and talha wine. A convivial celebration of Alentejo’s craft and character.
Our farewell dinner unfolds against the backdrop of vineyards at Fitapreta Winery, where contemporary cuisine and heritage wines bring the journey to a warm close.
Sixth night at Convento do Espinheiro
Day 8 Bid a fond farewell to Portugal
Before taking your complimentary departure transfer to the airport, take a moment to linger in the quiet cloisters of Convento do Espinheiro. The week’s flavours, the friendships, and the golden landscapes of Alentejo are etched in memory. This chapter may close, but the spirit of Alentejo endures: grounded, golden, and unforgettable.
Alternatively, extend your stay and continue your journey of discovery. Speak with your Signature Collection travel expert to explore the possibilities.
