After pick-up at our meeting hotel in Lisbon we will shuttle (~1.5hrs) to the ancient pre-Roman settlement of Évora. There will be time to have lunch (if you haven’t already) on your own in the town center while we set up bikes for a short ride (4mi.) through the historic streets to our hotel for check-in. Casual (non-cycling) clothing is adequate for this brief test ride. In the early evening, we will meet for dinner and an overview of the tour. We will be spending the next three nights at the Convento do Espinheiro, a 15^th-century recovered convent.

Cycle into the countryside this morning on your way to the visually stunning whitewashed village of Igrejinha, where the buildings are cheerfully trimmed in bright colors. Visit a family-run prickly pear farm to sample juice made from their fruits or tea from the flowers. Our last stop is at a cork factory to see the many uses for cork and how it is transformed from tree bark into various products. You can cycle from here back to Convento do Espinheiro, or shuttle in the van.

UNESCO sites, small farms and a charming white and blue village are some of the highlights on our morning ride from the hotel to Arraiolos village – famous for its long history, local pastries, beautifully embroidered wool rugs, and the views from the castle. Much of the cycling is via a bike path built on an old railway. In the afternoon we visit the Fitapreta Winery for a tasting (included). Experience the 14^th century palace setting as we get our first sample of some award-winning Portuguese wines! We return to Convento do Espinheiro after the ride. Dinner is on your own tonight.

Most of the route today is on a brand-new, peaceful, traffic-free, cycling path, hopping off the path here and there to enjoy some quaint little villages en route. Highlights along the way include leather artisans in the traditional village of Nossa Sra. de Machede, pottery masters São Pedro do Corval, and the mysterious Castle of Valongo. Visit a winery (included) where their best wines are still aged in massive clay pots. Spend the next two nights at Horta da Moura near Monsaraz.

Choose between cycling or using your time to rest and explore Monsaraz on your own today. Given its strategic location and the massive view from the hilltop castle, going back to pagan times virtually every major civilization in the West – Celts, Romans, Goths, Muslims, Jews, and Christians – has used the location as a stronghold. The bike route passes by some megalithic monuments on your way to the lake. Lunch is on your own today – either at the lake, or in Monsaraz.

Today’s ride takes you to the marble capital of Portugal, one of the largest marble producing areas in Europe. Known locally as “white gold,” marble not only shapes the actual landscape of the region, but it has also provided (literally) the building blocks for the streets – yes, marble streets! – as well the area’s most towering buildings. After lunch and a visit to an impressive, fortified sanctuary with a captivating history, you’ll enjoy a rare view over vibrant, colored lagoons formed by marble extraction. Continue cycling to Vila Viçosa, a small village often described as an open-air museum. We spend the last two nights of our tour here in a perfect blend of history and comfort at Pousada de Vila Viçosa, established in the 16^th century as an “aristocratic convent” primarily housing women from noble or wealthy families.

Today’s ride is fairly easy, providing us with the perfect opportunity to take our time. Pedal from tavern to tavern stopping to savor local delicacies – petiscos (Portuguese snacks) – along the way, trying not to overeat! Marvel at all the marble when we reach Estremoz – don’t forget your sunglasses today! Climb the 13^th century castle’s “donjon” tower for more unforgettable views before cycling back to Estremoz alongside vineyards and marble quarries. Explore more artesans’ shops and enjoy a celebration dinner on our last night in Vila Viçosa.

Sadly, it is time to say goodbye to the Alentejo region. After breakfast (included), we transfer you back to Lisbon at 10am. Drop-offs will be at our meeting hotel in Lisbon between noon and 1pm. If you are flying out today, we ask you to arrange your departure flight for 5pm or later.