Start off from Lisbon, an ancient place, which as stories hint was founded by Ulysses and harboured many famous explorers. Baking red tile roofs, fish sold from doorways, windows hung with washing and bird cages and small narrow streets is what the old city, Alfama, is made up of. Lisbon’s oldest district, which escaped destruction in 1755, has been inhabited since the 5th century, and today is a maze of streets, overlooked by the battlements of the medieval castle. It is a wonderful place to begin our trip and we take a private guided tour of the city with Rita & Jose, residents of this illustrious place.

A lovely morning start to some cycling as our winding country roads lead us into the Unesco Heritage city of Évora by way of small hidden villages and a rail to trails path. Arrive in Evora, with its twisting cobblestone streets giving hint of its Moorish heritage. Let your imagination run wild as you spy the huge 17th century aquaduct and Roman temple of Diana with its Corinthian columns, you'll only wish you brought your toga! Staying in one of Portugal´s most famous pousadas, the enchanting Loios Convent, you are in Évora´s heart.

Continuing on, we cycle across the taste-bud tingling Redondo wine region, stopping enroute to tour and taste at a local vineyard. Remember not to over indulge as you still have some cycling to do! A late afternoon cycle brings us to the interesting market town of Estremoz. A most dramatic cityscape, its medieval castle looms over the town’s cobbled streets and we make our way up to it to stay the night at this pousada. As the light in the countryside dims, we take our dinner in the great dining room in this most impressive building.

It is hard not to stop and stay in this pretty town with its many nice examples of Art Nouveau architecture and tasty tarts but the road awaits and we continue our exploration by journeying onto Vila Viçosa, famous for its elaborate Ducal Palace, home to the last royal family of Portugal. The route takes us into this town’s orchard area, its glowing marble quarries and ending in the town´s tranquil tree-lined avenues and quiet plazas. So pretty is it that it was even given by King Afonso IV as a wedding gift to his bride, Doña Brites. Stay in the elegant monastery pousada with its verdent garden and hidden niche chapels.

A relaxing day through the peaceful area and its tiny villages with their traditional tileworks and Moorish forts. It is an area known for its brilliant coloured ceramics and it will be hard to not want to take some home when you pass the outside stalls with their brillant shades of pottery glazes. Visit a pottery workshop before an arrival at Monsaraz, boasting an awesome hilltop castle and a panoramic vista of the of the Guadiana River which separates Spain from Portugal. Relax here, admiring the sunset over the two countries.

After breakfast for those who are keen, we take a short morning cycle ride through the lake reigion to finish our journey with a true sense of accomplishment at the Portugal-Spain border. Look back at the route we´ve travelled together before going back to the hotel for a final coffee and a wave goodbye to this lovely area and each other before transfering back to Lisbon for onward afternoon connections. Boa Viagem!