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 start our trip and we take a guided tour of the city.

We transfer out of the bustle of Portugal's capital city, to the pretty place of Arraiolos, where the craftspeople of this region have perfected the art of weaving and their woollen cross stitched tapestries. Here take a cycle around this pretty area to warm up your legs and then relax in the village soaking in the scenery with a glass of wine.

A lovely morning start to some cycling is our trip to the Unesco Heritage city of Évora with a stop at the famous prehistoric dolmens of the area. Arrival in town, and we have a guided tour of this city, its cobblestone winding streets giving hint of its Moorish inheritance. Let your imagination run wild when you wander the Roman temple of Diana and its Corinthian columns, you'll only wish you brought your toga! Try out the tasty local specialities like Alentejo Gaspacho of the area in the quaint cafes and bars lining the plazas and squares.

A short morning cycle brings us to the interesting town of Estremoz. A most dramatic cityscape, its medieval castle looms over the town’s cobbled streets. A tour around the area takes in the many small villages and towns serving this area's two most beloved commodities, wine and tasty sweet cakes.

It is hard not to stop and stay in this area’s attractive villages but the road awaits and we continue our exploration by journeying onto Vila Viçosa, famous for its elaborate Ducal Palace. The route takes us into this town’s orchard area and its tranquil tree-lined avenues and quiet plazas. So pretty is it that it was even given as a wedding present to Dona Brites, the wife of King Afonso IV.

A relaxing day through the peaceful area and its tiny villages to end it with an arrival at Monsaraz, boasting an impressive 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.

An early morning birdsong stroll is what you have time for before we must say goodbye to this lovely area and make our way back to the hustle and bustle of Lisbon where we will make our transfers for early afternoon.