Deep Into the Alentejo ⏤ Portugal

Day 1: Pick up in Lisbon

On our first day in Lisbon you’ll be picked up at 9:30am. After check-in, you will be delved into two important components of our Alentejo tour: wine with Os Galiardos, the terroirists and so-called activists of authentic wines; architectural modernism and its legacy with architect Frederico Valsassina; and their combination at Herdade o Freixo, a splendid winery that might as well be a museum of contemporary art. You’ll be able to relax with serendipity time in Lisbon, followed by a stimulating dinner.

Day 2: Custard Tarts, Artisan Crafts and Sunset Seranades

Day two will commence with a quest for the perfect pastel de nata at a real Lisboa institution: Pasteis de Belém, where the fabled custard tarts have been satisfying sweet tooths since 1837. Sated, we’ll then uncover Lisbon’s history of azulejo tiles through decorative arts museums, monasteries, ateliers and more: seeking inspiration at the Museu Nacional do Azulejo and handpainting your own tiles; visiting the artisan Ruí in Bicesse at Azulejos Artesanal. At sunset we’ll be serenaded by Julio Brecho on a private cruise, all before winding down for dinner and a restful night’s sleep...

Day 3: Experiencing Nature’s Gifts

Departing Lisbon, we’ll transfer to our next two-night resort to check in, relax and recharge at the understated countryside retreat. Once we regain our energy levels, we are in for a fascinating geologic tour of the nearby land with the savant Manuel Calado, followed by a picnic lunch in a serene setting. We’ll take to the winery of Esporão, part of the Alentejo’s cork oak forests, and wind down for dinner at Sabores de Monsarez, till the sun sets and the sky is dark. Then we’ll head to Alqueva to stargaze under one of the darkest, clearest skies in the world, to observe the stellar bodies that connect us to the earth.

Day 4: Sunrise to Sunset

We will experience a beautiful tour of the Alentejo from a beautiful perspective in a hot air balloon. In the afternoon, we will take a tour with a local wine producer and visit a small traditional wine talha maker to learn more about the roots of Portuguese winemaking.

Day 5: Explore the beautiful nearby town of Evora

We’ll take a ride assisted bike tour to Herdade do Freixo for wine tasting in an architectural gem, before strolling through Evora and taking lunch at a typical tavern. Visitors can opt to go for a Lusitano horseback tour at Monte Velho, or go to the Almendres Cromlech with archeologist Mario Carvalho to learn about the megalithic complex. We’ll check in to Casas Caiadas, which hints at hushed relaxation, and we’ll relax and recharge. We’ll stay in for a relaxing dinner at the end of an active day.

Day 6: Explore the Hilltop Town of Estremoz

We will explore the hilltop town of Estremoz, enjoy some wine history and tasting with a wine producer at an awe-inspiring facility and have dinner at a local organic family wine farm accompanied by the delightful winemaker.

Day 7: Farewells

On our last day in Portugal, we’ll visit a local market so you can pick up some souvenirs to bring back home. We’ll sit down for our last lunch with a special wine tasting at Herdade dos Outeiros Altos, a family-run affair, and learn all about their production. Our bags packed full with sun-drenched clothes, we’ll travel back to Lisbon, remembering to bring the slowed-down rhythms of Alentejo back to our everyday life.

Day 1: Pick up in Lisbon

You will be picked up in Lisbon at 9.30am to transfer to our first amazing retreat - a luxurious farmhouse on the Alentejo coast. After checking in, we will take advantage of the stunning location and enjoy a day on horseback with a picnic lunch. We will visit a hidden distillery and finish the day off with a relaxing welcome dinner on the farmhouse.

Day 2: Morning Hike

We will start the day right with a beautiful coastline hike and enjoy a picnic out in nature. In the afternoon, we will visit a local winery that has earned a solid international reputation with the quality of its wines for a tasting and dinner among the vines.

Day 3: Vineyards on Horseback

After breakfast, we will transfer to our next hotel – a unique family estate that is certain to impress! We will relax and savor a lunch on the property, followed by a horseback ride through the vineyard and wine tasting. A local wine and olive oil producer will host us for an authentic dinner.

Day 4: Hot Air Ballooning

See Alentejo from a lofty perspective as we take a sunrise hot air balloon ride over the countryside. Later, our local host will give us a tour around the area and in nearby villages to meet artisans and learn the local history of arts and crafts,. We will be treated to a special dinner.

Day 5: Night Sky

Transfer to another lovely retreat for a two-night stay, check-in and time to relax. Afterwards, a fascinating geologic tour of the nearby land followed by a picnic lunch in a serene setting. We are in for a treat in the evening for a sunset followed by a night sky experience and an amazing dinner at the hotel restaurant.

Day 6: A Relaxing Morning

A relaxing morning with a beautiful breakfast and time to enjoy the pool. In the afternoon, we will take a tour with a local wine producer and visit a small traditional wine talha maker to learn more about the roots of Portuguese winemaking.

Day 7: Ride to Evora

We’ll then transfer to Evora – on ride assisted bikes if desired – to enjoy lunch at a local gem of a restaurant and make our way to the next hotel. This estate has everything you could possibly ask for in a retreat: hushed relaxation in a dream vacation home. After check-in, you will have time to kick back and enjoy the splendid surrounds. In the evening, we will make our way to a neighbouring village to meet a true artisanal olive oil producer for a story and dinner.

Day 8: The Hilltop Town of Estremoz

We will explore the hilltop town of Estremoz, enjoy some wine history and tasting with a wine producer at an awe-inspiring facility and have dinner at a local organic family wine farm accompanied by the delightful winemaker.

Day 9: Farewells

On our last day in Portugal, we’ll visit a local market so travellers can pick up some souvenirs to bring back home! We’ll sit down for our last lunch with a special wine tasting at Herdade dos Outeiros Altos, a family-run affair, and learn all about their production. Our bags packed full with sun-drenched clothes, we’ll travel back to Lisbon, remembering to bring the slowed-down rhythms of Alentejo back to our everyday life.