Hidden Portugal - Discover the Essence of the Alentejo

Portugal’s Alentejo region is a land of golden plains, whitewashed villages, and centuries of living history. From cork forests and scenic trails to lively antique markets, this journey is a feast of colour, flavour, and discovery — a tour designed for the curious, where each day offers a new and unforgettable experience.

Try your hand at traditional cheese-making in Redondo, sip wines matured in ancient clay amphorae and wander the grand halls of the royal palace in Vila Viçosa. Meander through the medieval streets of Évora - European Capital of Culture 2027, enjoy a sun-drenched vineyard picnic, and set off on an off-road jeep adventure — all in a region where heritage is not just preserved, but lived.

Our Head of Sales & Marketing, Ellen Walker, has nurtured a deep love for Portugal over several decades, returning time and again to places that feel like second homes and friendships that have stood the test of time. It has long been her dream to share the Alentejo — often called the “Kitchen of Portugal” — with others, creating a tour that reveals the authentic heart and soul of this remarkable region.

ITINERARY

Day 1: Welcome to the Heart of Alentejo
Your Alentejo adventure begins with a flight from London Heathrow to Lisbon before travelling into the rolling countryside of Portugal's most authentic region. Nestled among olive groves and peaceful landscapes, the charming village of Redondo welcomes you with its relaxed pace of life and traditional character. Check into the historic Hotel Convento de São Paulo, a former convent transformed into a unique countryside retreat. As evening falls, meet your fellow travellers over a welcome drink before enjoying a delicious dinner showcasing the rich flavours of Alentejo cuisine. Surrounded by centuries of history and tranquil surroundings, this is the perfect introduction to the region's renowned hospitality.

Day 2: Cheese, Culture & Songs of the Serra d'Ossa
Today is a celebration of Alentejo's proud culinary and cultural heritage. Follow the famous Cheese Route and step inside traditional dairies where generations of producers continue the art of handcrafted cheesemaking. Discover ancient techniques, meet local artisans, and even try your hand at creating one of the region's most treasured delicacies. Later, experience the beloved Alentejo tradition known as the "11 O'Clock" gathering. Once a daily ritual for agricultural workers, this social custom comes alive through regional tapas, local wines, stories, and laughter shared in true Alentejo style. The afternoon takes you into the beautiful Serra d'Ossa, where rolling hills, cork forests, and panoramic viewpoints reveal some of the region's most spectacular scenery. At the secluded Hermitage of São Gregório, enjoy a memorable performance of traditional Alentejo singing accompanied by regional wine tasting. Before returning to Redondo, pause at the historic Padrão de Montes Claros, a monument commemorating a defining chapter in Portugal's fight for independence.

Day 3: Pottery, Bread & Rural Traditions
Immerse yourself in the everyday rhythms of rural Alentejo. Begin in Redondo's celebrated pottery workshops, where skilled artisans transform clay into colourful ceramics using techniques passed down through generations. Watch intricate designs emerge by hand and discover how these crafts continue to preserve the region's identity. Continue into the countryside to experience authentic farm life. Meet the animals that contribute to local cheese production, learn about sustainable farming practices, and gain insight into traditions that have shaped Alentejo communities for centuries. The day concludes with a visit to a traditional bakery, where wood-fired ovens fill the air with the irresistible aroma of freshly baked Alentejo bread. Witness time-honoured recipes in action and enjoy a taste of one of Portugal's most cherished staples. Return to your hotel for a relaxing evening at leisure. 

Day 4: The Marble Kingdom of Vila Viçosa
Depart Redondo and travel through a landscape shaped by one of Portugal's most valuable natural treasures: marble. Along the Marble Route, discover dramatic open-air quarries and learn how this extraordinary stone has influenced the architecture, economy, and artistic heritage of the region for centuries. Arriving in elegant Vila Viçosa, enjoy time to stroll through streets lined with gleaming marble façades before visiting the magnificent Ducal Palace, former residence of the House of Bragança and one of Portugal's most important royal residences. Continue exploring the town's rich heritage with visits to the Church of Nossa Senhora da Conceição, Portugal's patron saint, as well as the medieval castle that overlooks the surrounding plains. Later, journey to the UNESCO city of Évora for check-in.

Day 5: Estremoz Treasures & Ancient Wine Traditions
Step into the artistic and cultural soul of Alentejo. This morning, explore the historic town of Estremoz, renowned for its marble architecture and vibrant antiques market. Wander through stalls brimming with vintage finds, local crafts, and regional delicacies while soaking up the atmosphere of one of Alentejo's most authentic traditions. Visit the fascinating Puppet Interpretation Centre, dedicated to the famous Estremoz clay figures recognised by UNESCO as Intangible Cultural Heritage. These colourful characters tell stories of local life, humour, and history through a uniquely Alentejan art form. From the impressive Estremoz Castle, admire sweeping views across the endless plains before continuing to nearby Borba. Here, uncover one of the world's oldest winemaking traditions: Talha wine. Dating back to Roman times, these distinctive wines are fermented in large clay amphorae using methods unchanged for centuries. Enjoy a guided tasting and discover the flavours of a truly remarkable wine culture.

Day 6: Discovering Timeless Évora 
Today is dedicated to one of Portugal's most captivating cities. A guided walking tour reveals the extraordinary layers of history that make Évora a UNESCO World Heritage Site. Wander through charming, cobbled streets, admire whitewashed houses adorned with colourful details, and discover monuments that span Roman, medieval, and Renaissance eras. The remainder of the day is yours to enjoy. Browse artisan boutiques, relax in traditional cafés, explore hidden squares, or simply absorb the atmosphere of this beautifully preserved city at your own pace. Every corner of Évora tells a story waiting to be discovered.

Day 7: Vineyards, Adventure & A Farewell to Remember
Your final full day showcases the landscapes and wines that have made Alentejo internationally renowned. Embark on an exciting jeep adventure through the Serra do Redondo, following scenic trails that wind through vineyards, cork forests, and rolling countryside. Along the way, enjoy spectacular views and a deeper understanding of the region's unique ecosystem. Continue to a prestigious wine estate where a leisurely picnic awaits among the vines. Surrounded by peaceful landscapes, savour local produce and regional flavours in an unforgettable setting. A guided winery visit reveals both traditional and modern approaches to winemaking, followed by a tasting of carefully selected wines that capture the character of Alentejo in every glass. This evening, gather one final time for a special farewell dinner in Évora, celebrating the friendships, experiences, and memories created throughout your journey.

Day 8: Departure
After breakfast, transfer to Lisbon airport for your return flight to London Heathrow.

NB: Exact order of excursions may vary according to local conditions and tour manager’s discretion.

Please note the maximum group size on this tour is 23 passengers.

Tour Grading: This tour is graded as moderate due to time spent walking and standing for viewing at attractions. Please visit the mobility page of our website, or call our team prior to booking if you have any questions.

INCLUDED

• Return scheduled flights from London Heathrow to Lisbon
• Three nights’ accommodation at the four-star Hotel Convento de São Paulo based on shared occupancy of a twin/double room
• Four nights’ accommodation at the four-star Vila Gale Evora based on shared occupancy of a twin/double room
• Five dinners and three lunches (including one tapas lunch and one picnic lunch)
• All tours and entrance fees as detailed
• Airport transfers and full coach touring itinerary
• Tour manager throughout

NOT INCLUDED

• Double for sole use supplement - £450
• Meals other than those stated
• Items of a personal nature such as drinks, laundry, telephone calls etc
• Porterage and gratuities

HOTELS

Hotel Convento de São Paulo
This unique four-star hotel is located in Aldeia da Serra d’Oss. Set within a beautifully preserved 12th-century monastery, the hotel offers a peaceful retreat surrounded by nature and history. Many of the rooms are former monks’ rooms, now elegantly restored with antique furnishings and modern comforts.
Hotel Website 

Vila Gale Evora
This modern four-star hotel is located just a short walk from the historic centre of Évora, a UNESCO World Heritage city in Portugal’s Alentejo region. It
offers two restaurants, a spa with sauna, and swimming pool.
Hotel Website 

We love to receive feedback from our customers. Their views help us to keep improving the ours we offer. If you have been on this tour and would like to submit a review, please log in to our client area here and fill in the short form.

Recent Reviews

"The convent was an amazing place to stay and a real highlight of the tour, with beautiful surroundings and a wonderfully peaceful atmosphere. I also loved the visits to the rural villages and meeting the local artisans, which gave a genuine insight into traditional life and crafts in the region." Anonymous, travelled May 2026

"Staying at the Convento de São Paulo was a real highlight of the trip, set in a beautiful area with wonderful landscapes and a peaceful atmosphere. Exploring the surrounding villages was equally enjoyable, especially seeing the local artisans at work and experiencing the authentic character of the region." Mrs W, travelled May 2026

"We particularly loved staying at the beautiful Convento de São Paulo — it was so lovely that nowhere else could quite match it! We also greatly enjoyed visiting the remarkable Herdade do Freixo and the al fresco meal at the Hermitage of São Gregório. The warm welcome from local people and the traditional singing was a highlight. Our local guide Maria was excellent, particularly around Évora, her home town, where her local knowledge and enthusiasm really brought the place to life." Richard Last, travelled May 2026

"The first hotel, the former convent, was outstanding and a real highlight of the tour. The whole tour was extremely enjoyable." Patricia Richards, travelled May 2026

"One of the highlights of the tour was meeting local people who took such genuine pride in sharing their way of life with us. Their warmth and hospitality made the experience feel very authentic and memorable. Ellen did a wonderful job throughout the trip, and our local guide, Maria Joao, was fantastic — generously sharing her extensive local knowledge and bringing each place and experience to life." David Rhodes, travelled May 2026

"The visit to the marble quarry was fascinating and gave a real insight into the region’s craftsmanship and industry. I also especially enjoyed the visit to Herdade do Freixo, for the architecture." Mr P, travelled May 2026

"One of the most memorable moments of the tour was listening to the women singing traditional local songs in the chapel. Their beautiful voices and heartfelt performances created a truly moving atmosphere and offered a wonderful insight into the local culture and traditions. It was a very special and unforgettable experience." Anonymous, travelled May 2026

"I enjoyed every part of the tour, it was a truly memorable holiday from beginning to end." Ms P, travelled May 2026

"The programme was excellent, and Ellen and Maria worked together brilliantly to make everything run so smoothly. The Convent Hotel was special and added so much charm to the trip. It was also a real pleasure meeting the local village people, who were incredibly warm and welcoming. Their friendliness and constant smiles made the experience even more memorable. Overall, it was a superb holiday, and we felt very well looked after throughout." Anonymous, travelled May 2026