Alentejo Bike Tour

Your guides will greet you in Lisbon and drive east towards the Spanish border. The Alentejo region is a striking contrast to the bustling metropolis of Lisbon, with its unhurried pace of life, cork tree quintas, hundred-year-old olive groves, and flocks of sheep that roam the meadows. A beautiful lunch awaits amidst the olive trees at our boutique wine hotel. Set in the heart of the Alto Alentejo wine region, this enchanting estate was once home to the prominent Basilii family who inhabited the property in the 14th century. After a bike fitting and safety briefing, we’ll set off on a ride through the surrounding countryside, an undulating landscape of gold and green. Back at the hotel, enjoy a welcome drink and settle in before gathering for an evening of wine and contemporary Alentejo cuisine at the estate’s restaurant.

A gourmet breakfast prepares us for a ride through the gently rolling countryside of upper Alentejo. Pass through the dreamy scenery of world-class vineyards before we pause for a mid-morning coffee next to a wild stream where the locals plunge. Our ride continues along the western edge of the São Mamede mountains to a beautifully renovated farmhouse where we’ll enjoy a picnic-style lunch, prepared by our friends Walt and Ilde. Choose to hop in the van or bike all the way back to our hotel where you can take the rest of the afternoon to relax by the pool, explore the grounds of our historic hotel, or stroll through the surrounding vineyards. Tonight, we’re invited to the tower in the main house to learn how to make a medley of local Alentejo dishes with a local chef. Our class is followed by the dinner you helped prepare, paired with wines from the estate.

Our ride today takes us through the idyllic villages and fertile plains of Alentejo. Stop for a coffee before continuing to our friend Vasco’s family farm for lunch and some true Portuguese hospitality. Afterwards, we’ll ride to our next hotel—a meticulously restored homestead tucked among vineyards and cork oaks. Settle in and spend some time exploring the estate or unwind by the pool. Later, regroup for a hands-on workshop to learn the art of pão Alentejano. Baked in a wood-fired oven, this traditional bread is widely considered the finest in Portugal. Our day ends in the restaurant, where a meal crafted from fresh, local ingredients is served alongside the bread we baked together.  

Today’s ride is one of the week’s most challenging, as we pedal past rows of gnarly olive trees, pristine vineyards, and whitewashed farms. In the town of Redondo, we visit an artisan potter at work in his studio, watching as these traditional pieces are hand painted. From there we continue our travels over rolling country plains to Nossa Senhora de Machede, where we’ll have lunch at one of our favorite local restaurants. End the day with an optional ride all the way to Convento do Espinheiro, our luxurious hotel built around a 15th-century convent or hitch a ride in the van. This evening, join your guides for a guided walk through the UNESCO World Heritage city of Évora, wandering centuries-old streets and squares from the intriguing Chapel of Bones to the Roman Temple. Dinner follows at your discretion: your guides can suggest a few favorite restaurants in Évora, or you may prefer to return to your hotel for a laid-back meal from the convent’s once-upon-a-time monastic kitchen.

Our first stop this morning is a local cork producer, where we’ll learn about harvesting and processing this uniquely sustainable material—and why it thrives here in particular. Afterward, spin through pastures, vineyards, and oak groves, where the only sounds are the chirping of birds and the bells of grazing sheep. We arrive at a 14th-century estate that has been rejuvenated at the hands of a Portuguese wine wunderkind. After touring the cork-walled winery, we’ll head into in the medieval cellar where a wine-paired lunch awaits. Choose to finish the short ride back to Convento do Espinheiro or take a lift in the van. Tonight’s farewell dinner will take place at the hotel’s Divinus restaurant.

Relax this morning over a well-deserved gourmet breakfast before our drive back to Lisbon, where your guides will take you to your hotel or the airport.